road trip planner from boston to maine

15 Stops on a Boston to Bar Harbor Maine Coast Road Trip Itinerary

Lobsters and lighthouses. Charming towns and rocky coasts. The best way to discover the beauty and uniqueness of Vacationland is with a Boston to Bar Harbor road trip along the Maine Coast. I’ve driven this way many times and each time I discover something new. After so many trips to Maine, I put together this one to two-week Maine coast road trip itinerary from Beantown all the way up to Acadia.

If you are traveling from Boston to Bar Harbor, you will want to take at least a week to explore the Maine coast. Of course, you can drive straight through in under five hours, but there is so much to see on the Maine coast.

This Maine coast road trip includes some of my favorite places to go in Maine in the summer , with stops in:

• The Maine beaches region
• Maine’s midcoast including Boothbay Harbor, Rockland, and Camden
• Acadia National Park

After spending a few days around Bar Harbor, you can then take a fast way back home or continue Downeast off the beaten path to the New Brunswick border.

Where to Stop on Coastal Maine Road Trip

Note: This post may contain affiliate links. If you click a link and make a purchase, I may receive a small commission. All opinions are my own.

Day 1-2: Maine Beaches

The first region you will encounter on your Maine coast road trip will be the Maine Beaches. Of course, if you have even more time, you can always add in stops in Salem , Gloucester , Newburyport, or Portsmouth on your way up to Maine.

With a one-week itinerary, plan on spending at least two nights exploring this region. You can always break up two to three nights between two destinations to really get a sense of the differences between the various towns.

Your first stop in Maine is just across the border in Kittery. Kittery is known for its extensive shopping outlets, some of which you may not find in every outlet mall. But I don’t come to Maine to shop, at least not at brand-name outlets.

My first stop is usually at Bob’s Clam Hut , just north of the Kittery outlets on Route 1. While Bob’s is a popular tourist stop, they actually have some of the best lobster rolls and fried clams around. The lines are long for a reason. And yes, the lines are loonnngg. Don’t be surprised to find the parking lot full and the wait for food an hour long in high season.

On my recent trip, I decided to skip Bob’s and try something new so I went where the locals hang out and tried the quieter Chauncey Creek Lobster Pier. You can watch the lobster boats coming in while eating fresh seafood right on Chauncey Creek. But I’ll be honest with you, I still prefer Bob’s.

For a scenic stop, you can also check out Fort McClary, a historic fort in Kittery Point where you can walk along the battlements and get a view of two lighthouses in the distance. There are picnic grounds here for a scenic lunch.

Fort Foster is another great spot for spending a day outdoors, with excellent views of the entrance to Portsmouth Harbor and Whaleback Light, Portsmouth Harbor Light, and Fort Constitution. But you do need to a pay $20 per car parking fee.

Your next stop in the Maine Beaches, about 15 minutes up the coast, should be York Harbor and the York Beaches. Foodies will want to make a pitstop at the Stonewall Kitchen factory store on Route 1 in York. Here you will find all the delicious Stonewall Kitchen sauces, dressings, and other food products, as well as cooking classes and the culinary school, and a cafe.

York Harbor is a quaint oceanfront area with a few rocky beaches that are connected by the York Cliff Walk. If you are looking to stay overnight in this area, the York Harbor Inn is perfectly located right across from the town park and the entrance to the Cliff Walk . The Stage Neck Inn is another great choice.

The York Beaches, both Long Sands and Short Sands Beach are great for surfing, but the accommodations around the beaches are primarily seaside motels. This is also where you will find a majority of the gift shops, restaurants, and souvenir shops. Nearby you have family attractions like York’s Wild Kingdom, mini golf, and more. If you are looking for a quaint downtown and nice sand beaches, head a little further north to Ogunquit.

Cape Neddick

Before you get to Ogunquit, be sure to stop in Cape Neddick, just five minutes further, at the Nubble Lighthouse . Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door (bring cash!) or Dunne’s Ice Cream down the street.

From here, follow Shore Road 15 minutes north into Ogunquit. If you are looking to stay in this area and are ready for a splurge, overnight at the luxurious Cliff House Maine .

Ogunquit is very popular with travelers and many of the hotels and motels are not located right on the beach. So if the beach is your priority and you want to stay overnight, be sure to check and see if your accommodations are truly beachfront. The town itself is quaint and upscale, but also touristy. You will find a mix of fine dining options along with your typical tourist clam shacks and seafood restaurants. Ogunquit makes a nice place for a day trip.

We like to stop into Perkins Cove , the small shopping and dining area on the harbor. I’ve eaten at Barnacle Billy’s in Perkins Cove and it was fine, but there are probably better options in the area. In Perkins Cove, you can take in the view of the incoming fishing boats from the Footbridge, or take a 1.25-mile stroll along Marginal Way, past stately inns and rocky beaches.

Kennebunkport

If you haven’t stopped yet, you will want to bed down for your first night in the popular town of Kennebunkport , just another 25 minutes further north. There are many options near downtown Dock Square, but I would recommend a stay at The Inn at English Meadows . This lovely mid-18000’s Greek Revival-style inn is located in Kennebunk’s Lower Village, just a half-mile walk to downtown Dock Square. Perfect for romantic getaways , this bed and breakfast has been tastefully renovated to offer historic charm with modern luxuries such as Frette fine linens, toiletries by Malin+Goetz, and comfortable Vera Wang beds.

There are some accommodations that can fit a family, but families may prefer a resort such as Nonantum Resort , just south of town and on the water, even if not on the beach.

In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack. We also like to head out of town to Cape Porpoise Chowder House , which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. I’d highly recommend a scenic drive around Cape Arundel, although it will cause some serious house envy!

If you are looking for beach time, Gooch’s Beach is wide and long and great for families, but street parking is limited so get there early. You can also try nearby Goose Rocks Beach or Colony Beach.

Old Orchard Beach

Thirty minutes north of Kennebunkport is another popular beach town. Families love Old Orchard Beach not only because it has a gorgeous, flat, wide beach, but kids also love the rides at Palace Playland and the arcade games at the pier. This section of the Maine beaches feels almost out of place given the rest of the Maine coast, almost as if someone plucked it off the Jersey shore and plopped it in Maine.

My daughter also loves going to Funtown Splashtown , an amusement park/water park, nearby. But if the boardwalk vibe isn’t your jam, you might want to skip over Old Orchard Beach and try Scarborough Beach State Park instead.

Day 3-4: Portland

I would recommend spending one to two nights in the Portland and Casco Bay region, 25 minutes north of Old Orchard Beach. On your way into town, be sure to stop at Portlandhead Light in Cape Elizabeth. It is a great place to scramble on the rocks, walk along the coast, and enjoy those lighthouse views.

We love staying in the Old Port area at the Press Hotel , AC Hotel Portland , Courtyard Marriott, Hilton Garden Inn, or Cambria Old Port. Downtown Portland is a foodie city, with many great restaurants to try. You can also take a tour on the Beer Bus or stop at one of the many breweries nearby. My favorite one to tour and visit is Allagash Brewing Company. For some great lobster with a view, go to Luke’s Lobster on the wharf.

You can hop on a ferry boat and explore some of the islands in Casco Bay, or sign up for a lobster boat tour, where you can learn all about lobstering and help pull up the traps. Best of all, you can eat what you catch! If you don’t want to stay in town, you can also enjoy a car-free couple of nights at the Inn at Diamond Cove on Great Diamond Island.

Read more: weekend in Portland Maine

Freeport (day trip from Portland)

From Portland, you can also take a day trip to Freeport, about 20 minutes north of Portland. Famous for being the headquarters of L.L. Bean , it has become a shopping mecca. In addition to the large company store and L.L. Bean outlet, many other designer outlets and outdoor outfitters have set up shop in town.

You can also stop in for a tasting at Maine Beer Company and sample some of their IPAs. If you are looking for a great lobster roll nearby, head down to the water at Harraseeket Lunch and Lobster Company .

Day 5-6: Maine’s Mid Coast

After your time in Portland, it is time to move on to Maine’s midcoast. This area has miles of coastline, hundreds of islands, and countless charming coves to explore. Picture an open hand pointed down with outstretched fingers and you can imagine the many peninsulas that jut out into Casco Bay and the Atlantic Ocean.

It is good to base yourself in this region for at least two to three nights, broken up between two or more destinations. Although many vacationers might decide to spend a week on Orrs Island and be quite content.

Your mid-coast exploration can start off in the town of Brunswick, a 30-minute drive from Portland, with a walk across the Androscoggin Swinging Bridge . This pedestrian bridge connects Topsham and Brunswick, offering beautiful views of the Androscoggin River. After, take a stroll through downtown Brunswick, home to Bowdoin College.

Harriet Beecher Stowe, the author of Uncle Tom’s Cabin and member of the Underground Railroad, lived and worked in town and her house is now a designated National Historic Landmark. If you need a good lobster roll in this area, head to Cameron’s Lobster House.

From Brunswick, head south on Route 123 to the tip of the peninsula for lunch at Erica’s Seafood . This little hidden gem offers seafood fresh off the boat that you can enjoy at picnic tables overlooking the harbor. From there, turn towards Route 24, which leads down through Sebascodegan Island to the town of Harpswell, Orr’s Island, and Bailey’s Island.

You will get to the end of the line when the road reaches the ocean at Land’s End gift shop. Backtrack a little to the Giant’s Stairs Trail . You can park at the All Saints by-the-Sea Episcopal Chapel and walk along the path that runs parallel to the rocks that make up the Giant’s Stairs. When I went, I was hoping for something more like Giant’s Causeway in Northern Ireland. The rock formations aren’t that unique but it is still a cool view and fun place to explore.

If you have more time in the area, you can spend a day at Reid State Park or Popham Beach, or visit the Maine Maritime Museum in Bath. You may also want to line up for a lobster roll at Red’s Eats in Wiscassett, just don’t make my mistake, be sure to get there before they close! Give yourself about an hour to get from Giant’s Stairs to Boothbay Harbor.

Boothbay Harbor

Boothbay Harbor was one of the first places I visited in Maine, over twenty years ago! I was happy to see that it has only gotten better since my last visit, although the good old Tugboat Inn is still there! This time I stayed at the lovely Harborage Inn , which was located right on the water and just a short walk into the center of town.

In town, there are so many cute shops, from Maine Sea Bags to Sherman’s Books, along with other gift shops, galleries, and boutiques. You will also have your choice of restaurants including Mine Oyster, Kaler’s Lobster, Boathouse Bistro, Ports of Italy, and Shannon’s Unshelled.

For lunch, I would recommend eating fresh seafood outside at Boothbay Lobster Wharf . It is across the bay from town but you can easily walk across the pedestrian bridge connecting the two sides of town.

A very popular thing to do in Boothbay Harbor is to take a whale-watching tour. However, since I’ve been whale watching many times, on this trip I opted for a puffin cruise with Cap’n Fish out to a wildlife preserve on Eastern Egg Rock instead. This 2.5-hour cruise passes by lighthouses on the way, with opportunities to see dolphins or even whales.

The boat is large so it can only get so close to the island, however, the puffins often raft up in the water along the shore so you are bound to see plenty of puffins. Just bring along some good binoculars or a super zoom lens because puffins are small and you won’t get to see their cute, colorful beaks without a little assistance.

Read more: things to do in Boothbay Harbor, Maine

Damariscotta

From Boothbay Harbor, it is only 15 minutes over to Glidden Point Oyster Farm on the Damariscotta River. I was hoping to take a oysters and wine-tasting cruise with Damariscotta River Cruises , but unfortunately, they weren’t running on the day I was in town. So an oyster farm tour seemed like the next best thing!

Eighty percent of Maine’s oysters are farmed in the Damariscotta River! My tour at Glidden Point Oyster Farm explained why the river was the perfect spot for oysters and its history that goes back thousands of years to pre-Colonial times. After learning about the farming process, I stepped up to the window to order some oysters to taste on their outdoor patio. I even learned to shuck an oyster! And I was thrilled to learn that Glidden Point ships nationwide.

If you have more time to stay in the area or prefer a quieter town versus Boothbay Harbor, Damariscotta has a very cute but small downtown. Stop into the Sherman’s Maine Coast Book Shop and Sheepscot River Pottery. You can also visit the Whaleback Shell Midden State Historic Site.

You can stay at the Newcastle Inn and have dinner at King Eider’s Pub or Newcastle Publick House. Locals love Shuck Station Raw Bar and if you want to head a little out of town for some beer tasting, stop into Oxbow Brewing Company at their rural farmhouse brewery.

Pemaquid Point Lighthouse

From Damariscotta, it is a 20-minute drive down to the Pemaquid Point Lighthouse , which can be a great spot for sunset. Of course, when I went it clouded up so I didn’t stick around that long, but that’s ok because I was able to get to my next stop in Rockland a little early.

From Bristol, it is an hour’s drive to Rockland. I took Route 32 through Bremen and it worked out perfectly when I came across a park with fields of beautiful purple and pink lupines stretching down to the water. If you have time, also stop at the Marshall Point Lighthouse (you may have seen this in Forest Gump.)

Rockland is the Art Capital of Maine, a bustling town with art museums, galleries, shops, and restaurants on a working waterfront. It is also a port for Maine Windjammer ships and even small-ship cruises, so it attracts its share of day trippers as well.

It is certainly a larger and more touristy town than many of the others along the Maine coast, but I loved it and returned recently to spend some time before my Maine Windjammer Cruise on the Schooner Heritage.

Make time to visit either the Farnsworth Art Museum , which celebrates Maine’s role in American art, or the Contemporary Arts Museum downtown. If it is open, you can also stop into the Project Puffin Visitor Center to learn about all things puffin. It is a fun town to explore, check out the many murals and public art, and shop at the many boutiques (my favorite was Barefoot in Denim !)

There are so many great spots to eat in town. I had an amazing dinner at Primo, a farm-to-table Italian restaurant just a short drive from downtown. I’d also recommend Rock City Coffee and Rock Harbor Brewing.

If you have time, just south of town follow signs for the breakwater. It is about a mile walk out along the breakwater to the lighthouse at the end, but it is a fun outing on a nice day. Another day trip option is to take a ferry to Vinalhaven, which is known for its beautiful scenery, rocky coast, and granite quarries.

The best place to stay in Rockland is 250 Main Hotel . This modern, art-forward hotel has a rooftop deck overlooking the waterfront and spacious rooms.

Read more: things to do in Rockland , Maine

A 15-minute drive from Rockland, Camden is another popular town on Maine’s midcoast. There are excellent views of the Camden harbor front from the Camden Public Library, and the lawn is a great spot to enjoy a picnic or relax and soak up the view.

Downtown there are many shops and restaurants, such as The Waterfront Restaurant, Peter Otts, and Fresh and Go. If you would rather stay in Camden instead of Rockland, the Lord Camden Inn is right in the center of everything, while the Camden Maine Stay Inn will be a bit quieter and laid back.

Outside of downtown, you can enjoy scenic views from the top of Mt. Battie in Camden Hills State Park. Also, try hiking along Maiden’s Cliff or the Megunticook Ocean Lookout Trail. Unfortunately, during my visit the fog rolled in and I could barely see to drive through that area, let alone take in a scenic view.

Before you get to Bar Harbor on Mount Desert Island, you may also want to stop at the Penobscot Narrows Bridge & Observatory or visit Fort Knox State Park. That was my plan too but with the fog, it wasn’t worth it.

Day 7-8: Bar Harbor

Camden to Bar Harbor is about an hour and forty-minute drive, although you may want to stop in Ellsworth before arriving on Mount Desert Island, for a beer tasting at Fogtown Brewing Company. Instead of staying in the town of Bar Harbor, I chose to stay at Terramor Outdoor Resort about 15 minutes from Acadia National Park and Bar Harbor.

If glamping isn’t your thing, you may want to opt for the luxurious Claremont Hotel in Southwest Harbor or the charming Salt Cottages overlooking Hulls Cove. Of course if you are going all the way to Bar Harbor, you will want to spend some time downtown and walking along the Shore Path along Frenchman’s Bay. From town you can also take a whale watching cruise. Bar Harbor is also a fun town for shopping and restaurants.

If you are visiting Acadia National Park in the summer, be prepared for crowds and make reservations if you want to drive to the top of Cadillac Mountain for sunrise. (You could try this Acadia National Park sunrise hike instead!) To avoid crowds, also check out these things to do near Acadia .

A Maine coast road trip should be on everyone’s bucket list. It is hard to get tired of seeing fishing boats bobbing in a harbor, lighthouses standing tall over rocky coasts, and eating endless amounts of lobster and seafood. Hopefully, this itinerary makes it easier to plan your trip!

Read More Maine Articles

• Best places to go in Maine in the summer
• Things to do in Portland in the winter
• 7 Must-Try Outdoor Adventures in the Maine Highlands
• Maine Highlands Road Trip
• Maine Road Trip Itinerary

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: March 23, 2024

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From Boston to Bar Harbor: a New England road trip [+Map]

This New England road trip itinerary will take you on the scenic route from Boston to Portland then to Maine’s Mid Coast and Acadia National Park. You’ll experience the east coast food – like lobster and seafood – and take in the beautiful Maine lighthouses that still guide the ships along the rocky coastline. Find an interactive map at the bottom of this post.

What you need to know about New England

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NOTE: Travel is not recommended at this time. These posts are here to serve as inspiration when we can explore again. Hey there – this post likely contains affiliate links, which means I earn a commission (at no extra cost to you) if you purchase from them. This helps me earn a few dollars to run this website.

When the Women in Travel Conference announced that they would be heading to Portland, Maine for their three-day summit, I immediately started planning for an epic New England road trip along the coastal regions. While I’ve crossed Maine off of the places I’ve been – I drove through it when I did an east coast road trip a couple of years back – I never did get to the coast.

The summit was the perfect excuse to explore more of Maine’s incredible coast. While this was not the exact itinerary I took – since I did spend three days at a conference – this guide is how I would split up my trip if I did not have a conference to attend.

New England is one of the oldest colonial regions in the United States, comprising of six states in the northeastern section of the country. Spanning from Maine to Vermont, New Hampshire, Massachusetts, Rhode Island and Connecticut.

Known as the birthplace of colonial America, New England is now home to nearly 15 million people. The area is known for its hills (with part of the Appalachians running through it) and for its rugged, unforgiving coastline. Because it is so far north compared to the rest of the USA, I find that its climate is similar to the east coast of Canada.

That means winters are long and snowy, and the summers are short but popular with visitors. Fall is peak season for New England when millions of visitors come to the region to take in the fall colours. In spring, the trees are in bloom. The coastal areas of Maine are just waking up for the season in spring, and many attractions open in mid to late May, around the American Memorial Day holiday.

New England is made up of 38 different regions. This New England road trip itinerary focuses on only four, Metro Boston, Southern Maine/ Portland, Mid-Coast and Acadia/ Down East.

Unless you have a car yourself and can drive the whole route, my suggestion is to wait until day five or six of this New England road trip itinerary to rent a car and here’s why: Boston is hazardous even to walk. Seriously, you’ve got to keep your eyes peeled at all times, and I would not wish driving in the city on anyone. However, it’s very walkable and has a public transportation system to get you from point A to point B.

You can then take the Amtrack Downeaster to Portland. It takes 2h 30m, and it’s a lovely train trip up the coast. After a couple of days in Portland, you’ll want to rent a car for the rest of the way to hit all the lighthouses and lobster shacks on the way to Acadia National Park.

A majority of this New England road trip will take you along the United States Route 1, the longest north-south route in the US.

Route 1 takes you from the Canada-US border in Maine to the tip of the Florida Keys. While you won’t be travelling all 3,818km (2,369 miles) on this New England road trip, you’ll be taking the scenic route through Maine’s Mid Coast, stopping at various small coastal towns and beautiful lighthouses.

If you’d rather zip from Portland to Acadia National Park without stopping, then take the I-95.

RELATED: 10 treasures to discover in New Brunswick

The first stop you’re going to make on a New England road trip is in Boston. Whether you can drive up or fly in, spending at least two nights in this historic city is a must. Boston is the epicentre for cultural activities and historical architecture. And the best part is it is all walkable.

Day one: Land in Boston, explore the downtown

There is so much to see in Boston, but two full days will help you get the lay of the land and see some of the best of what Boston has to offer. On day one, you’ll land in Boston and explore the city’s most famous neighbourhood: Beacon Hill.

Next up is the Downtown, where you’ll find history lurking behind every corner and enjoy Boston’s little central park, the Boston Common. Start your morning off right at a coffee shop and later, dig into some of the best grilled cheese in Boston.

Beacon Hill and Acorn Street: Is it even a trip to Boston if you don’t visit the city’s most famous neighbourhood? Beacon Hill is where Boston was settled by colonials back in the 1600s and is known for its redbrick row houses and stunning façades.

There was an actual signal from which Beacon Hill got its name. You might be surprised to hear that it was not a great place to live for several centuries before it was gentrified in the 19th century. Make sure to visit Acorn Street, the most photographed street in the US, early in the morning, since you’ll want to capture the morning light on the stunning cobblestone street and red brick houses.

Massachusetts State House: This golden domed building, located on the outskirts of Beacon Hill, is where the seat of government is in Massachusetts. Dating back to 1798, this building is actually the second statehouse in Boston. Inside is filled with history and traditions dating back to the beginning of the country, so it’s definitely worth a tour!

Boston Common and Public Gardens: Opposite the state house is the Boston Common and Public Gardens, Boston’s central park. It’s the oldest city park in the US, where you can sit and relax, stroll along the many pathways, watch people play a game of baseball, visit the site of the Great Elm, throw a coin into the Brewer Fountain, or catch a musical performance at the bandstand.

The Public Garden sits adjacent to the Boston Common. There, you’ll find a pond, several flowerbeds, statues and a trail. Sit on one of the park benches, like the one Robin Williams used to sit by or jump into a Swan Boat in the summertime. Don’t miss the little ducks in the bronze statue called Make Way for Ducklings. People like to dress up the ducks in different outfits. They were little judges when I was there.

Boston’s Freedom Trail: The Freedom Trail is a 4km pathway through the heart of Boston’s downtown that stops at 16 historically significant locations. You can do the trail yourself, or take a tour to soak in all the history . On the trail, you’ll see the Granary Burying Grounds, Massachusetts State House, King’s Chapel, The Old Corner Bookstore, Old State House, Boston Massacre Site, Faneuil Hall, the U.S.S. Constitution and more.

The Boston Globe: As a journalist, I had to stop and see the home of the (new) Boston Globe building. (Have you seen Spotlight?!) It’s located in Exchange Place, which is built with the facades of the old stock exchange building.

Fan Pier Park: If you want lovely views of the Boston skyline, then cross the bridge to Fan Pier Park, on the way you’ll see Boston’s old swing bridge, which closed to pedestrians in 2014. Walk along the pier and then turn around to see the marvellous Boston cityscape.

Boston Tea Party Museum: This floating museum allows you to re-live some of the critical moments of US history and take a peek into what life was like during the American Revolution.

Tatte Bakery and Café: Grab your breakfast at this adorable cafe; one location is located right on Beacon Hill. I suggest a delicious chai latte and a morning bun, a sweet pastry that tastes like a cinnamon bun and a croissant had a baby.

Quincy Market: Located near the Faneuil Hall, Quincy Market is this marvel of a building. It houses hundreds of shops from food to clothes to keepsakes. Along the middle of the market, you’ll find so many food options that exist only here. Try the Boston Chowdah or the baked beans that gave Boston its nickname: Beantown.

Thinking Cup: End your first night in Boston at the Thinking Cup, a bistro near the Boston Common. They have so many incredible sandwich options, but I suggest building your own grilled cheese – it’s to die for!

Day two: Explore Back Bay and Fenway Park

Day two of this New England road trip itinerary will take you into Boston’s Back Bay neighbourhood and Fenway Park. Back Bay is a beautiful area known for its stunning residential architecture, New England’s tallest buildings and shopping districts. Walk along the green space, called Commonwealth Avenue Mall, between Commonwealth Ave’s streets. 

Women’s Memorial and history trail: Women had (and still have, obviously) a huge part in the shaping of Boston. Often overshadowed by the influential white men at the time, we are starting to understand the role that women have played in history. It is so important that we don’t lose these accounts. The Boston Women’s Memorial is a sculpture in the Commonwealth Avenue Mall that depicts Phillis Wheatley, Abigail Adams, and Lucy Stone. This memorial is one of the stops on the Boston Women’s Heritage Trail – an important experience in this historical city.

View this post on Instagram Hello Boston! It’s me @iamfirstmehta, here for #TakeoverTuesday. With spring coming ahead here’s a last glimpse of snowy Trinity Church ❄️ A post shared by Boston Convn & Visitors Bureau (@visitboston) on Mar 12, 2019 at 8:13am PDT

Trinity Church: Likely one of the most famous churches in Boston’s Back Bay area, Trinity Church has been a staple of the skyline since it was built in the 1700s. You can take a self-guided tour of the church or go on a guided tour ($10 or free on Sundays). The building itself has been on American Association of Architects list of top 10 buildings in the United States for centuries.

Boston Public Library: Not only is the Boston Public Library the third largest public library in the United States, but it is one of the most historic. It was founded back in the mid-1800s. Today you can visit the central branch for free on your own or a public tour. Make sure to check out the Grand Staircase, Bates Hall, the courtyard and the various galleries.

Sky Walk observatory: If you’ve read any of my other posts, then you know I love to get views from above. Boston has one of those birds-eye views of the city at the Prudential Center. It costs $21 USD, which includes the ride up and down, an audio tour, the Dreams of Freedom exhibit and a multi-media movie theatre.

View this post on Instagram Happy Friday! Where are you going this #weekend? #mapparium #boston #travel A post shared by The Mary Baker Eddy Library (@mbelibrary) on Nov 3, 2017 at 12:45pm PDT

Mapparium: Probably one of the coolest experiences is at the Mapparium at the Mary Baker Eddy Library in Back Bay. You get to walk inside a three-story tall globe made of stained glass. It was built in 1935 and shows the world as it was at the time (notice how some of the political borders and names have changed).

View this post on Instagram 26 days until Opening Day at Fenway, Boston’s favorite sign of Spring! ⚾ ? @clusk61 A post shared by Boston Convn & Visitors Bureau (@visitboston) on Mar 14, 2019 at 8:44am PDT

Fenway Park: Known as “America’s most beloved ballpark,” Fenway Park is home to the Major League Baseball team Boston Red Sox. Not only is it the oldest MLB ballpark in the United States, but it’s more than just a place to watch a game. You can take a behind the scenes tour of Fenway Park to get the insider details of how the place operates. Tours take you on a 60 minute guided walk . If you don’t have the time, you can take a 15-minute tour that brings you to the archives, a roof-top deck and ends with a panoramic view of the stadium. There are also other tour options based on what you would like to see in Fenway. You can buy tickets online up to 30 days before the date, after that you can chance getting a ticket at the door.

Brunch at Sonsie: With all this walking, you’ll want to stop for a bite to eat. Why not a delicious spot for brunch? Sonsie is a classy bistro known for its brunch. From seafood to pancakes to sandwiches to eggs, their menu will please just about everyone.

Seafood at Saltie Girl: When on the east coast, you have to dig into the local cuisine, which means seafood! They create every fish and seafood dishes that you could imagine, from smoked fish to seafood towers to fried lobster and waffles.

Budget – HI Boston Hostel : While the price of this hostel is higher than I’ve paid for a dorm bed, I can’t deny how much I enjoyed the HI Boston. Not only was it cozy and clean with beautiful décor, but the staff was incredibly friendly. Plus it had great WiFi and a delicious free breakfast.

Midrange – The Revolution Hotel : Boston is not cheap to stay. Their mid-range prices are more like luxury prices, and you’ll generally find cheaper hotels the further you stay out of the downtown. The Revolution Hotel is a trendy boutique hotel outside the city centre and offers a cool meeting/ working space called Conspire.

Luxury – The Godfrey Hotel Boston : This hotel is as fancy as it gets in Boston. From beautiful décor to the location right in the heart of the city, I’m sure you’ll enjoy your stay at the Godfrey Hotel.

RELATED: The ultimate weekend getaway to Portland, Maine

There are so many reasons why you need to visit Portland, Maine. Not only is it the craft brew capital of the United States, but the city has been named the 2018 restaurant city of the year . With over 200 establishments calling Portland home, it isn’t any wonder that there are more restaurants per capita than any other city in the US (except San Francisco). Trust me; you’re going to love it here.

Day three: arrive in Portland, brew bus tour

After taking the Amtrak Downeaster from Boston to Portland, you’re going to get settled before jumping on the Brew Bus. Trust me; you’re going to want to sample as many places as possible. Then take a bite into your first lobster dish.

Disclosure: I was invited by the Maine Brew Bus on one of their tours through the Women in Travel Summit conference. All opinions are my own.

Maine Brew Bus : Let me just say that I’m not a big drinker. I’ll enjoy a cocktail or two every once, and a while and I love Ontario cider, but it’s very rare for me to actually have a drink. And beer is just out of the question. But I had the opportunity to go on a brew tour through the Women in Travel Summit, and I can honestly say it has changed my perspective on drinks.

Not only was our driver and host hella funny, but each establishment was welcoming and thoroughly explained their passion to us. Our first stop was Foundation Brewery . I don’t like beer, truly, but I really enjoyed two of the three beers I tasted. Plus, when one of them, Pale Blue Dot, which was created to celebrate Earth Day and to support the local Sebago Clean Waters project, I was sold.

Our second stop was at Eighteen Twenty winery, whose owner Amanda explained how her love of wine drove her to make it out of something that grows well in Maine: rhubarb. She had me in stitches explaining how she got to the point of actually selling her craft, and I have to admit, rhubarb wine might be better than actual wine JUST SAYING.

Our last stop was at Hardshore Distillery for my poison of choice: gin. Founder Jordan showed off his incredibly cool copper distilling beast and explained every effort he and his team puts into making their smooth-as-silk gin.

Maine Mead Works: I also had to check out Maine Mead Works, because (and this is true) it sounded bada$$. Who else pictures Vikings and Lord of the Rings when you think if mead? Well, think again, because this place is classy! I suggest trying the tasting flight, which is based on the bottles they have in season.

Mead is made through the fermentation of honey, water and any other flavours you wish to mix in. The Honeymaker Mead at Maine Mead Works is made through the South African method, which is apparently different than what you would think mead would be. PS: Try the Lavender Mead. It’s the first alcohol I’ve EVER brought home from a trip, so that explains how great it is.

High Roller Lobster Co: What started with two dudes and a food truck, turned into this trendy spot in the heart of Portland’s downtown. High Roller Lobster Co is just one of the man places to get a classic lobster roll, but did you know you can also get a lobster grilled cheese, lobster taco and a lobster on a stick? Yup. All right here.

Day four: Explore Old Port

After *buzzing* into town yesterday (ha get it?), you’re going to want to spend your second day in Portland (and fourth on the New England road trip) exploring Portland’s old port and historic district.

Harbor Fish Market: You’ll find the freshest fish and seafood right in the heart of the Portland waterfront at the Harbor Fish Market. See where many of the city’s restaurants get their catch of the day at one of the oldest fish markets on the east coast. Don’t worry; they won’t throw their fish at you!

Old Port: In Portland’s old port, you’ll still find cobblestones and red brick buildings paying homage to this old New England city. Wander the street and take a peek into the several one-of-a-kind shops. Make sure to stroll along Fore Street and Wharf Street and don’t miss the Longfellow street art. Henry Wadsworth Longfellow was a poet from Portland who is known for his poems capturing the plight of the Acadians.  

Exchange Street: Where everything is happening in Portland. Seriously, from shops to restaurants, all the cool kids are hanging out on Exchange Street. Here is where you’ll find the infamous Holy Donut.

Historic Waterfront: Zigzag through the floating piers and watch the boats zoom by at the Historic Waterfront District. Here you’ll even find a piece of the Berlin Wall!

Congress Street: Find more of Portland’s history on Congress Street, including Congress Square Park, Public Market House and Monument Square. Keep your camera out because you’re going to want to keep snapping photos!

Becky’s Diner: Go where the locals go to find the best eats in town. You’ll find that at Becky’s Diner on Commercial Street. Try the unbelievably delicious blueberry pancakes (made with Maine blueberries) or the lobster and Swiss omelette! PS: As a Canadian, I have to tell you, don’t you dare skimp on the real maple syrup.

The Holy Donut: Find out what all the fuss is about at the Holy Donut. These fresh and delicious doughnuts are made from Maine potatoes. Yup, that’s right potatoes. And you’re not going to have just one. There’s almost always a line up out the door so be patient, because they are freaking worth it.

Portland Lobster Co: Ready for lobster roll round two? The Portland Lobster Co was voted the best lobster roll four years in a row. Plus they have a great location right on the water with a picnic-style area that can’t be beaten. Go try it for yourself!

Day five: Munjoy Hill, Eastern Promenade and Portland lighthouses

Now that you’ve spent a day wandering around the Old Port, on day five of a New England road trip, it’s time to get out of the downtown and see some of Portland’s other famous areas.

Munjoy Hill: Like Boston’s Beacon Hill, Munjoy Hill is a historic residential neighbourhood. Many of the old ship captains’ homes still stand facing the water like guards of their own. Technically starting at Washington Street and then surrounded by water on three sides, Munjoy Hill is one of the more affluent neighbourhoods in Portland. Like Beacon Hill, it wasn’t always that way. Today you’ll find a quiet area with beautiful views everywhere you look.

Portland Observatory: While the Portland Observatory looks very much like a lighthouse, it is not a lighthouse. Built in 1807 by Captain Lemuel Moody, the 26-metre tall structure was used as a marine signal tower for passing ships. Today you can climb the 103 steps to the top to get a wonderful view over Portland and the surrounding bay. Keep in mind that the observatory is only open from Memorial Day (late May) to mid-October and costs $10.

Sumner Park: For a free view of the city, and a great place to catch the sunset, head to the highest point on Munjoy Hill located at Sumner Park.

Eastern Promenade: The Eastern Promenade is a massive park that stretches along the Portland peninsula’s most eastern side. Here you can take a walk along the trails, or lounge on the beach and stick your feet in the ocean. The most southern point is Fort Allen Park, where you’ll find monuments to several wars in American history.

Portland Head Lighthouse: Next, head all the way to Cape Elizabeth south of Portland to visit one of the most famous lighthouses in the world: Portland Head Lighthouse. It’s also the oldest lighthouse in Maine.

George Washington commissioned the lighthouse before he became the first president of the US. The Portland Head Lighthouse is located within Fort Williams Park, which was operating as a military fort from the late 1800s until the mid-1960s. You can explore the old batteries that dot the coastline. New in 2019, out-of-town visitors will now have to pay $2/hour for parking within the Fort Williams Park.

Spring Point Ledge Lighthouse: Heading north, you’ll visit Spring Point Ledge Lighthouse, a short, squat lighthouse with a small, rocky path jutting out from the shore. It dates back to 1897, but today you can tour the lighthouse and Fort Preble, where it is located. It is adjacent to the Southern Maine Community College.

Bug Light: Also known as the Portland Breakwater Light, Bug Light is a tiny lighthouse located in South Portland. What’s interesting about this lighthouse are the fake Corinthian columns that decorate the side, are actually used to hide the seams of the iron façade. The land surrounding Bug Light has an interesting tale. During the Second World War, the area was used for a shipyard for the New England Shipping Company, where the crews, of mostly women, built 236 Liberty Ships, a military-grade cargo ship, for the war efforts. You can see a reconstruction of a hull’s frame at the park today.

Disclosure: I was invited on a tour with the Real Portland Tour through the Women in Travel Summit conference. All opinions are my own.

Real Portland Tour : Did you know that Portland burned to the ground, not once but four times in its history? I sure didn’t. That’s just one of the insane facts I learned from local Derek of Real Portland Tour. The 90-minute tour takes you along old roads of Portland and to the three lighthouses mentioned above. Along the way, Derek explains the city’s fascinating history and might even do a Portland rap for you! I highly suggest this knowledgeable and entertaining tour if you have limited time in Portland.

Bite into Maine: As the name suggests, you’re going to bite into Maine cuisine at this food truck located at Fort Williams near the Portland Head Lighthouse. Owner Sarah has concocted several versions of the classic lobster roll. Each at mouthwatering as the other. I tried the classic Maine style with Maine-made root beer and finished it off with a delicious blueberry whoopie pie. Dare I say it, I think this way my favourite lobster roll to date.

Duckfat Friteshack: Just writing about these delicious fries from Duckfat is making me drool. Duckfat makes their fries the Belgian way – double fried – but in duck fat, instead of oil. They were crispy, melt in your mouth, delicious. They also have a restaurant located in the Old Port, if you want more of a sit-down dinner.

Eventide: Get fresh oysters, a warm lobster roll and other tapas-style dishes at Eventide. This trendy spot serves up some delicious food. And I have to say, I really enjoyed the warm, buttery lobster roll. It’s different than anywhere else I tried.  

Budget – Black Elephant Hostel : This independently-run hostel is the only hostel operating in Portland. It’s definitely a funky place to stay just outside of the Old Port area in Portland. They have twelve different rooms that can accommodate a range of people.

Midrange – the Spring Point Inn : Run by the hospitality students at Southern Maine Community College, the Spring Point Inn is a lovely place to rest your head for the night. There are eight cozy rooms, with many overlooking the Spring Point Ledge Lighthouse. While the Inn is located outside of the city of Portland, it’s a comfortable place to stay in the mid-price range.

*Disclosure: I was hosted by Portland Harbor Hotel for a night. All opinions are my own.

Luxury – Portland Harbor Hotel : If you want to feel treated like a queen right in the heart of Portland, then stay at the Portland Harbor Hotel. This lovely old hotel is Portland’s only AAA four-diamond hotel. The recent renovation gives the entire hotel a nautical theme, perfect for this east coast location. The service from when you check in to the thoughtful turndown service was exemplary. I could have stayed here in luxury forever.

Next up on the New England road trip itinerary is Maine’s Mid-Coast. Once you’ve got a taste of Maine’s most populous city, then you’re going to head north for the perfect place to relax and see the spectacular rugged coast.

Day six: Route 1 to Camden

You’re officially halfway on your New England road trip itinerary, but the best is yet to come. Start your morning with a coffee (see suggestions below) and hit the road!

Eartha Globe, Yarmouth: First stop is to visit Eartha, a giant, moving globe located at Garmin’s Maine office in Yarmouth. In fact, it’s the world’s largest revolving globe. As an avid traveller, I just had to check it out. It was built inside an atrium in 1998 at the DeLorme headquarters; Garmin bought the company in 2016.

L.L. Bean flagship and giant boot, Freeport: When you’re on a road trip, you have to check out giant roadside attractions. And the L.L. Bean boot is one of them. Located at L.L. Bean’s flagship store and outlet in Freeport, the giant boot and the surrounding shopping complex is a must experience. It’s the first and largest L.L. Bean store in the world and its open 24/7!

Androscoggin Swinging Bridge, Brunswick: The Androscoggin Swinging Bridge is a pedestrian suspension bridge that crosses the Androscoggin River in Brunswick. Stop here for a little rest or stroll along the Riverwalk, because this is where you’ll hook onto the Scenic Route 1 for the rest of the trip.

Whaleback Shell Midden State Historic Site, Damariscotta: The Damariscotta River is known for its oysters, who love the cold, deep water. This place has been a gathering point for Indigenous Peoples for millennia before settlers arrived in the Americas. Evidence of this is at Whaleback Shell Midden State Historic Site, where heaps of oyster shells, discarded by the Indigenous peoples, were found.

Pemaquid Point Lighthouse, Pemaquid Point: This lighthouse is located at the southern point of one of the peninsulas along Maine’s coast. It was built way back in 1827 on the orders of US President John Quincy Adams. What’s neat about this lighthouse is where it’s located. The geological surroundings are striking, and the rocks look like they are folding into each other and the sea. Try to spot some of the sparkly white rock running like ribbons along the darker grey rock. PS, I totally called this place “Permasquid” like a squid with a perm, but it’s called Pemaquid.

Owls Head Lighthouse, Rockland: Next stop is Owls Head Lighthouse near Rockland. Here, you’ll find a short lighthouse atop a hill. You’ll need to climb a few stairs, but the view is worth it. This little light overlooks the Penobscot Bay; you’ll just want to stare out into the sea forever.

Center for Maine Contemporary Art, Rockland: Take a break at the Centre for Maine Contemporary Art, located in Rockland. This art gallery is right in the heart of Rockland’s downtown, and perfect to stretch your legs and engage your mind. It’s open from 10am to 5pm, Wednesday to Saturday and noon to 5pm on Sunday. Admission is $8.

Rockland Harbor Breakwater Lighthouse, Rockland: For your last lighthouse of the day, don’t miss the Rockland Breakwater Harbor Lighthouse. Located just outside the town of Rockland, this cottage style lighthouse sits at the end of a 1.4 km (7/8 mile) breakwater. You can walk the entire length and get up close to the building. We timed ourselves. It takes 18 minutes to walk along the rocky outcrop. I suggest not doing this during bad weather, or you’ll be swept into the ocean.

Megunticook Falls, Camden: The Megunticook River runs right underneath the town of Camden, so when you get here you have to check out the Megunticook Falls, a cascade of water that runs right from underneath the stores and into the harbour. Make sure to go on both sides of the falls for different views!  

Downtown Camden: Camden is known as the Jewel of Maine, and it’s easy to see why, with its tree-lined streets, homey-atmosphere, and lovely ocean views. Stroll along the downtown and duck into one of the many antique shops. And don’t forget to search for a bite to eat!

Higher Grounds, Portland: Start your morning in Portland at Higher Grounds for coffee. They serve locally-roasted coffee and a variety of fine foods. Try their morning bun; it’s delicious!

Shuck Station Raw Bar, Newcastle: The Damariscotta River is known for the high-quality oysters that grow here. The cold, deep river is the perfect breeding ground for these delicious delicacies, so what better place to have your oysters and a shuck shack right on the river? Shuck Station Raw Bar does just that, plus they have a variety, depending on your tastes.

Sea Dog Brewing Co, Camden: Eat and drink your heart out at the Camden location of Sea Dog Brewing Co. From seafood to tacos to salads and burgers, they’ve got just about everything here. Plus you can sample their 10 different beers. Bottoms up!

Budget – Towne Motel: Located inside the town limits, this motel is a simple, yet affordable option for resting your head in Camden. The rooms are nautical themed to keep the with Maine coast vibe.

Midrange – The Inn at Camden Place: This Inn is located right on the Megunticook River in an old renovated factory. You’ll want to cozy up in their plush beds or sit at a chair by the window watching the river speed by.

Luxury – Grand Harbor Inn : This AAA four-diamond hotel is right in the heart of Camden, with views overlooking the harbour. Plus, this boutique hotel is pet-friendly, who can say no to that?!

You’re at the home stretch of the New England road trip itinerary. Spend the next two nights in Bar Harbor, right on the outskirts of Acadia National Park. On this leg of the trip, you’ll get up early for sunrise on Cadillac Mountain, wander the streets of Bar Harbor and walk along the rugged coast of Acadia National Park.

Day seven: route 1 to Bar Harbor

On day seven of the New England road trip itinerary, you’ll be taking Scenic Route 1 then leaving the highway to drive to Bar Harbor, a sleepy town in the offseason and a busy town in the summer and fall. That’s because Bar Harbor is the largest town next to Acadia National Park, where people flock to in the summer and go leaf peeping in the fall. But before you get there, you’ll want to stop at a few places first.

Main Street, Belfast: Like many small towns in America, Belfast has a beautiful and historic downtown. Take a quick stroll along the shops to see if anything catches your eye. Make sure to see the Belfast and Area Chamber of Commerce, which is situated in an old-timey gas station. Definitely one of the more colourful buildings in town.

Belfast Harbor Walk, Belfast: Hop onto the harbour walk path, which takes you through the Front Street Ship Yard where you can see some BIG boats in BIG slings being worked on.

Belfast Armistice Bridge, Belfast: You’ll take the path all the way until you reach the footbridge. The Belfast Armistice Bridge is a pedestrian bridge that crosses the Passagassawakeag River. It used to be an old rail line but was converted into a trail recently. Check out the River views from here.

Fort Knox, Penobscot: Next stop is Fort Knox! No, not that famous Fort Knox, which houses the US gold reserves. This is the other Fort Knox. It’s one of the best preserved military fortifications from the 1800s on the east coast. It was designed and built after the war of 1812, to protect the area from further British invasion. The troops here never saw military action. Today, the fort is open from May 1 to October 31. It costs $6 to enter, or $8 if you would like to visit both the fort and the observatory.

Penobscot Narrows Bridge and Observatory, Penobscot: The Penobscot Narrows Bridge is fairly new. It opened in 2006 as a replacement for the historic Waldo-Hancock Bridge that had corroded beyond repair. However, when building this bridge, the designers thought an observatory at the top of one of the support towers would be a cool idea. They were right. Today, you can take an elevator to the top of the word largest bridge observatories for views up and down the Penobscot River. You can get an $8 ticket that includes both Fort Knox and the observatory.

If you would like a free view of Fort Knox and Penobscot Bridge, then head across the river to Bucksport Veterans Park, in Bucksport, which is what I did since the observatory was not open at the time of my visit.

Main Street, Bar Harbor: You finally made it to Bar Harbor. Your first stop is to explore Main Street and surrounding downtown. Make sure to stop into any one of the unique shops along the downtown to get made in Maine products and souvenirs. Check out the Village Green and grab an ice cream at one of the delicious ice cream shops downtown.

West Street, Bar Harbor: Next head to West Street, which is the street nearest the harbour. This is where you’ll catch a boat tour if you elect to take one. You’ll want to take pictures at Agamont Park since it has such nice views over the surrounding bay. You’ll also want to come back here for dinner!

The Shore Path, Bar Harbor: For a quick walk, this 1.6 km (1 mile) round trip path follows along Bar Harbor’s sea wall. It passes by some of Bar Harbor’s most luxurious estates and gives excellent views of the surrounding bay and islands.

Sunset at Blue Hill Overlook: Make sure to check the time of the sunset when you go, because you’re going to want to take the drive up to Blue Hill Overlook for sunset. Because Blue Hill Overlook faces west, you’ll be in for a treat when the sun dips below the horizon. If you can’t get there for sunset, no worries, Blue Hill Overlook is still beautiful at other times of the day and should not be missed!

Bagel Café, Camden: Grab your fill of coffee and fresh bagels at the Bagel Café. Pick up two for the road! You never know when you might want a delicious snack!

West Street Café, Bar Harbor: Less of a café, more of a bistro, the West Street Café is a great spot to satisfy your hunger at dinner time. Try their lobster roll while you stare out their big windows to the sea!

Day eight: Sunrise and Park Loop Road

On day eight of the New England road trip itinerary, you’ll want to get up early for sunrise. Trust me; it’s worth it. Then, power through so you can explore the rest of Acadia National Park.

Sunrise at Cadillac Mountain: Up and at ‘em! It’s time for sunrise on Cadillac Mountain. Timing is everything. It takes about 30ish minutes to get from Bar Harbor to the top of Cadillac Mountain (don’t worry you can drive right to the top), which means you’ll want to time your trip to arrive about 30 minutes before sunrise since that’s when the colours are at their best.

Did you know? Cadillac Mountain is the supposedly first spot in Maine and the continental US to see the sunrise. While the exact place may be up for debate, the height of Cadillac Mountain and the beauty of the surrounding area certainly leads people to flock here every morning for a beautiful sunrise. Just bring warm clothes and a couple of blankets, because it can get pretty windy up there.

Blue Hill Overlook: If you didn’t get a chance to catch sunset last night, then drive over to Blue Hill Overlook to take in the beautiful surroundings with the sun at your back.

Duck Brook Bridge: Before jumping onto the Park Loop Road, take a small detour to see the Duck Brook Bridge, which is part of the dozens of carriage roads that wind throughout Acadia National Park. And who can pass up a quaint little waterfall?

Thunder Hole: Jump onto the Park Loop Road 43km (27-mile) loop around Acadia National Park’s most beautiful scenery. Much of the trip is one way, so make sure to stop at every place you want to stop, because you won’t be able to turn around. Because it’s one way, you can actually park on the right side of the road, which the left lane can keep traffic moving.

Stop at Egg Rock Overlook, Schooner Head Overlook, and Great Head for a quick hike, then make your way to Thunder Hole for high tide. A naturally forming cave lies beneath the rocky surface. At low tide, you can head down the step to have a peek inside, but at high tide, it’s a different story. The waves and the cave combine to create a thunderous boom, giving the place its name. Apparently, the best time to go is between low and high tide, where the waves are just right to make the thunderous boom and launch the spray nearly 40 feet into the air. It’s a natural marvel you don’t want to miss!

Otter Cliff Lookout: Another great scenic lookout stop is at Otter Cliff Lookout, located just a little further down from Thunder Hole. You can park in a small parking lot just off the road then make your way across the road to the overlook. Here you’ll get some amazing views of Acadia National Park’s rocky coast. I loved listening to the waves crash against the cliffs.

Little Hunters Beach: Next stop along the Park Loop Road is Little Hunters Beach. You can park in a small pull over and climb down the stairs to a beach that is hidden from view from the road. First, marvel at the little waterfall running right under the road. The beach is made up of smooth rounded rocks, created by erosion from the constant waves. You can hear the rocks scrape against each other as the waves roll back into the sea. It sounds like one of those rain sticks people had when I was a kid.

Jordan Pond: After stopping at Little Hunters Beach, the Park Loop Road heads back inland, cutting a path through the middle of the park. Pull over at the Jordan Pond parking lot and head down to walk along the shore of this lake. The two lumpy mountains to the north are the Bubbles, after their round shape.

A Slice of Eden, Bar Harbor: Just like the name suggests, a Slice of Eden is a delicious spot for heavenly food. They have everything from sandwiches to salads to breakfast foods to cakes and treats. You’ve got to try their whoopie pie, which is Maine’s official state treat (their official state dessert is blueberry pie.) For the whole story on that, you have to ask Derek of the Real Portland Tour!

Project Social, Bar Harbor: If you want a light lunch or dinner, or can’t decide what you want, then Project Social is where it’s at. This place is known for its tapas and craft cocktails.

Thirsty Whale, Bar Harbor : For pub fare and a spot that was recommended to me, head to the Thirsty Whale, a charming tavern in the heart of Bar Harbor. They’re known for their lobster rolls, fish sandwiches and homemade chowders. Definitely worth a stop!

Day nine: Western portion of Mt. Desert Island, back to Portland

It’s your last day on the New England road trip itinerary! I know, so sad, I bet the trip just flew by. After checking out a few places on the western side of Mount Desert Island, you can take the I-95 to rush back to Portland. If you’re trying to make it back to Boston, there’s the last Downeaster that leaves Portland at 6:15pm and arrives in Boston for 8:45pm. If you’re not rushing back, then take it easy and enjoy the rest of your trip!

Bass Harbor Head Lighthouse, Bass Harbor: In the western portion of Mount Desert Island, which is where the majority of Acadia National Park is located, you’ll find the Bass Harbor Head Lighthouse. This is also the southernmost point of the island. A Coast Guard family occupies the house next to the light, so respect their privacy, but you can get up close to the lighthouse and the original fog bell. Take the short Bass Harbor Lighthouse Trail to get some incredible views of the ocean, the red Acadia National Park rocks and the lighthouse all on one photo!

Wonderland Trail: If you want to take a short, easy hike while in Acadia National Park, then the Wonderland Trail is the perfect place to do that. This 2.5km (1.6-mile) trek is an easy in-and-out trail that takes you through forest before spitting you out on the rocky shoreline.

Choco-Latte, Bar Harbor: Fuel up your morning at Choco-Latte in downtown Bar Harbor. They have a lot of items made with fine chocolates, but you can also get breakfast food and sandwiches too. You have to try their chocolate latte! It’s delicious.

Budget – Quality Inn : This motel may have budget prices in Bar Harbor, but the digs are not. It was a cozy and comfortable stay, and the motel is just on the outskirts of town. It was the perfect medium between a short jaunt into town and access to the park. One morning, three deer decided to visit on the hill right behind the motel, a perfect little slice of nature, right in their backyard.

Midrange – Acadia Hotel : In the centre of Bar Harbor sits the Acadia Hotel, a friendly and comfortable boutique hotel with a winning location. You’ll enjoy the nautical themed rooms that are beautifully decorated. Plus Project Social is part of the hotel, so you don’t have to go far for a great bite to eat.

Luxury – Bar Harbor Inn : If you want to stay in luxury, then you’ll find it waiting for you at Bar Harbor Inn, a historic waterfront hotel. From their plush rooms to the stunning views of the ocean, this place can’t be beaten. They also have a water view infinity pool!

New England Road Trip Itinerary

From Boston to Bar Harbor, this New England road trip will take you to the best of the best along the coast. Visit historic downtown Boston, stroll the trendy Portland streets, take in the beautiful scenery along Maine’s Mid Coast, and finally enjoy some time outdoors at Acadia National Park.

Olivia Rutt

Olivia Rutt is the travel writer and photographer behind My Wandering Voyage, a travel website helping working millennials find time to travel. She shares insight in trip planning, travel inspiration and photography tips. Olivia hails from southern Ontario, Canada where she works in the media industry between travels. Follow Olivia on Instagram where she shares her travel photos, or catch up with her on Facebook or Twitter.

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Mywanderingvoyage.

Privacy Overview

Road Trip from Boston to Maine

Maine is known for its beautiful coastline and rugged inland scenery dominated by rivers, lakes and mountains. It's a great place to enjoy the great outdoors and is home to some of the country's oldest towns, where you'll find historic squares and quaint redbrick homes on the seaports looking out across the Atlantic.

The 960-mile road trip from Boston to Maine and back takes about 22 hours to drive. On the coast you'll pass York, Portland, Bar Harbor and Acadia National Park; then head inland to Bangor, Moosehead Lake, Greenville, Kennebec Valley and Bigelow Preserve.

This is a trip full of big, beautiful views, magical scenery and charming towns - the perfect ingredients for an unforgettable road trip. So, continue reading on the learn about the best route, our recommended stop and the best time to set off on this scenic adventure.

How far is Maine from Boston, and how long will the road trip take?

Boston and Maine are near neighbours, and you can make the 70-mile drive from Boston to York, Maine in just over an hour.

Once you've arrived in Maine, you'll have longer distances to cover, but fortunately, there's so much to see and do in the Pine Tree State that you'll find something to break up even the longest of stretches on your trip.

We'd recommend following our suggested round trip route below, which hugs the coast northeastwards as far as Acadia National Park then swings inland through Bangor to explore Baxter State Park, the Kennebec Valley and Maine Highlands.

This sets you up for a 775-mile circuit around the state which takes around 19 hours of driving, plus a little extra if you're making any extra side trips off our main route.

Add in a couple of hours for the drive back from Sebago Lake to Boston, and you're looking at a total of 22 hours 30 minutes for the complete, 960-mile road trip.

To help you with your route planning, we've provided more detailed driving distances further down the page.

You could drive the loop around Maine in just a couple of days if all you want is some great photographs and a lobster roll or two. But with so much to see, and hundreds of half or full-day hikes to choose from, we'd recommend taking at least a week.

Best road trip route from Boston to Maine

If you follow the interstate north from Boston, one of the first places you'll pass in Maine is York. Made up of four distinct towns – you might hear it called ‘the Yorks' – it's the perfect place to begin your tour around Maine.

With some of the best Maine Beaches right here, offering long stretches of sand, beautiful bays and stunning ocean views, where better to exit the interstate and begin to explore?

From here, you'll follow the Atlantic coast right the way to Acadia National Park, close to the Canadian border. This is a rugged and beautiful stretch of coast, so take your time exploring the inlets and islands that stretch out to the south of the highway.

Heading inland from Bar Harbor you'll soon find yourself driving through Maine's beautiful interior, where rivers, lakes, forests and mountains create a beautiful backdrop to any trip.

After passing Bangor and Medway you can enjoy views of Mount Katahdin, Maine's highest peak, and endless opportunities to enjoy outdoor pursuits, before the road starts to swing south again through the Maine Highlands and Kennebec Valley, passing Kokadjo and massive Moosehead Lake.

The circuit ends at Sebago Lake, one of the state's most popular destinations, and from here it's just a couple of hours back down the interstate to return to Boston.

Whether you're flying into Boston or you simply don't have your own transport in the city, renting a car for your road trip is something you'll want to take care of ASAP.

For an easy-to-compare view of rental options for your road trip from Boston to Maine, take a look at our partner site, RentalCars.com .

Road trip route from Boston to Maine: a round trip of the state

Follow Route 1 out of Boston then join the interstate heading north. Seeing as it's only a short drive up to Maine, you might like to detour towards the coast to visit Salem, Gloucester or Rockport along the way.

Otherwise, simply follow Interstate 95 (I-95) North all the way across Massachusetts and New Hampshire until you reach Portsmouth, where the Piscataqua River Bridge takes you into Maine.

Road Trip Route from Boston to Maine

Part 1: drive from york to ellsworth - a road trip through greater portland, mid-coast and downeast.

Once you've crossed over from New Hampshire to Maine, make your way north eastwards, keeping the coast on your right-hand side. You can either use the interstate here or hop onto the highway if you want to explore at a more leisurely pace.

You'll pass York and Kennebunkport before arriving in Portland, from where you'll take Route 1 to skirt around beautiful Casco Bay.

The highway then takes you on through Wiscasset and Thomaston. You might like to explore the miles and miles of rivers, inlets and rugged coast that sits to the south of the highway here, including Harpswell, Popham Beach, Georgetown Island and Boothbay Harbor.

Carrying on along Route 1 around Penobscot Bay, turn right when you reach Ellsworth and follow the road toward Trenton, where you'll cross the Mt Desert Narrows. Spend some time exploring Acadia National Park and Bar Harbor before returning along the route back to Ellsworth.

If you have a little extra time, detour east along Highway 1 here towards Schoodic Head, where the National Scenic Byway offers more fantastic views. Otherwise, simply continue up the highway from Ellsworth as far as Bangor.

Part 2: drive from Bangor to Greenville - a road trip through the Maine Highlands

From here, rejoin the interstate and follow it north as it runs parallel to the Penobscot River up to Medway. Then turn off the interstate and head towards Millinocket.

At East Millinocket you can take a detour up to North Penobscot to pick up the Katahdin Woods & Waters Scenic Byway, or continue on past Millinocket and join Golden Road on the narrow strip of land that separates Millinocket Lake and Ambajejus Lake.

Golden Road skirts the edge of Baxter State Park, where you'll find Mt Katahdin and dozens of amazing trails. Continue along Golden Road as it starts to swing back south again. When you reach Caribou Lake, which will be on your right, take the left fork and head towards Kokadjo and Greenville.

Here, you can spend some time exploring Moose Lake Scenic Byway, the Maine Highlands and the northern part of the Kennebec Valley, before continuing south through Abbot and Kingsbury Plantation to reach Bingham.

Part 3: drive from Kennebec River back to Casco Bay - a road trip through the River Valley and Lakes & Mountains

Follow the highway south the short distance to Solon, then turn onto Route 201A to cross the Kennebec River before taking Cross Town Road as far as Embden. Here, take Wentworth Road onto ME-16, continuing straight ahead onto Long Falls Dam Road where ME-16 swings round to the west.

With Gilman Pond to your left, continue on Long Falls Dam Road until you reach the southern tip of Flagstaff Lake. Here, you can park up to explore the trails of Bigelow Preserve or continue further along East Flagstaff Road to enjoy views out across the lake.

When you're ready to move on, return back along Long Falls Dam Road, turning right to briefly follow ME-16 west before taking a left onto the road to New Portland.

Next, head south past Farmington, Livermore Falls, Mechanic Falls and Casco, before continuing south onto Frye Island to enjoy some time on the shores of Sebago Lake.

From here, return to the highway, following Route 302 south as far as Riverton, where you'll rejoin I-95 to begin your drive back to Boston.

Best places to stop between Boston and Maine

Maine offers a fabulous blend of activity and relaxation, and there are some fabulous hotel stops along the route which let you combine the two seamlessly.

Watch the sunrise over the Atlantic in Bar Harbor

Around 8 hours and 30 minutes out of Boston, Acadia National Park is one of the must-see stops along this route and spending a night or two in nearby Bar Harbor gives plenty of time to enjoy the national park.

Ascend Cadillac Mountain, the first place in the US to see the sun each day (for 6 months of the year), or head to Thunder Hole where waves break impressively into a natural inlet. It's also a great place to see Maine's stunning fall foliage on display.

As well as being a gateway to Acadia National Park, there are great food and drink options in the town of Bar Harbor itself, and beautiful views out over the ocean. If you're lucky you might be able to see whales feeding in the bay here in summer.

One of the top hotels in town is Queen Anne's Revenge , a beautiful location known for its fantastically welcoming team, and for the immaculate design that runs through every room. You can really immerse yourself in the coastal vibe here.

The town was once a summer getaway for wealthy city dwellers, who helped to shape the streets into what you'll see today - take a walk through West Street Historic District to get a feel for the legacy they left behind.

Immerse yourself in nature in Greenville

On the northern stretch of the route, with around 8 hours of driving between here and Boston, Greenville is the perfect place to base yourself for a few days to explore parts of the Maine Highlands and Moosehead Lake.

Moosehead Lake is the biggest in Maine, surrounded by exquisite countryside views, and it offers some unique recreational activities. While you're here you should definitely take a moose-watching tour, where you'll try and track down these gentle giants in the wild.

You can take a steamboat cruise on Moosehead Lake to enjoy the views from a different angle, or enjoy boating, kayaking and fishing. Or head a little further afield to explore the Kennebec Valley, where you can go white water rafting or hike up to Moxie Falls.

If you're looking for a luxury retreat as you near the end of your road trip, the kind with sweeping lake views, immaculate design, unbeatable service and an excellent restaurant, then look no further than the Lodge at Moosehead Lake. A stay here really is an experience in itself.

With a luxury price point and a minimum stay requirement, this won't suit every traveler's road trip plans, in which case there are other options in the area.

As an alternative, we'd suggest Leisure Life, Greenville , which is spacious, and easy to get to from the highway. You can enjoy amazing views right out of the hotel and relax after a long day of hiking and driving in the hotel's bar or by the pool table.

Check out the coastal vibe in Portland

Portland is known for its cobblestone streets, red brick townhouses, Victorian mansions and thriving arts scene, so although you might have passed through Portland at the start of your trip, it's also a great place to spend a final night or two before returning to Boston.

Head to the Portland Museum of Art to catch a really varied and thought-provoking selection of exhibitions, ranging from contemporary pieces to works by some of art history's biggest names.

Then head to Portland Observatory. This ocean-facing signal tower is a reminder of Portland's maritime past, and all through summer you can take a guided tour to learn more about the city's ocean-going heritage.

Finally, before you hit the road, make your way to Old Port to enjoy the view out across the water one last time while you watch fishing crews haul in their catch of lobster.

Centrally located Portland Harbor Hotel stylishly combines modern design with hints of coastal chic , and it's a beautiful place to stay while you're in town.

There are some great cafes, bars and restaurants in the immediate vicinity, and most of Portland's main attractions are within walking distance.

Things to see on a road trip from Boston to Maine

You'll be spoilt for choice as you make your way around Maine - whether your preference is to spend time in the city, on the coast or exploring the great outdoors, there's something for everyone on this trip.

We've picked out some of the highlights, but one of the real pleasures of this route is the chance to stop off and explore the small towns, coastal scenery and big views that you happen upon as you drive.

Things to see on the way to Maine

• Salem, MA - Known for the infamous 17th century witch trials, this waterfront town has a number of witch-related museums and tours. You can also visit the Peabody Essex Museum, explore Salem Maritime National Historic Site, or head to the historic House of Seven Gables.
• Portsmouth, NH - The oldest settlement in New Hampshire is still a working port with plenty of history on display. Tour the historic houses, Strawberry Banke living history museum, or Seacoast African American Cultural Museum for different perspectives on the coast's history.

Things to see around Maine

• York - Head to York Beach for saltwater taffy and classic seaside fun, with Fun-O-Rama arcade, quirky cafes and live music, all looking out over Maine's beautiful sandy beaches and bays.
• Ogunquit - The town's name means ‘beautiful place by the sea' so enjoy a coastal walk or a stroll along one of America's best beaches. Ogunquit Museum of American Art is set in beautiful gardens by the sea (summer opening only).
• Broad Cove Reserve - Follow one of the walking trails here to enjoy more sea views from the sandy beach.
• Popham Beach State Park - Where the Kennebec River meets the sea you can swim, surf or stroll along the shifting sands at this popular state park. At low tide it's possible to walk out to nearby Fox Island, but keep an eye that the tide doesn't cut off the causeway before you return.
• Bath - Just outside the ‘city of ships' you'll find Maine Maritime Museum, or enjoy a fabulous seafood meal in one of the redbrick downtown restaurants.
• Reid State Park - Seabirds come here to nest in the dunes, rocks and sweeping sandy beaches which are also a fabulous place for humans to enjoy the coastline or hike up the headline for views across the park and islands.
• Augusta - Visit the Maine State Museum or the Old Fort Living History Museum to find out about the past of Maine's capital city. Then follow the River Rail Trail along the Kennebec River to enjoy beautiful views across the valley.
• Kennebec Valley - If you have time to take a fabulous scenic detour, head north from Augusta through Skowhegan, taking your time to explore the lower reaches of the stunning Kennebec Valley.
• St George Peninsula - Turn south from Thomaston to explore more of the region's rugged coastline, try some local wine, or visit the quirky Owls Head Transportation Museum.
• Rockland - Best known as the home of the Maine Lobster Festival, Rockland is also a meeting point for the arts, with Center for Maine Contemporary Art and the North Atlantic Blues Festival.
• Belfast - With its independent galleries, live music and Arts Walks, historic Belfast can be a buzzing place to stop if you're passing through in summer.
• Penobscot Narrows - Where the road crosses the Penobscot River, a massive observatory tower offers unbeatable views along the river and out to sea.
• Bar Harbor and Acadia National Park - This rugged and wild national park offers fabulous views out to sea, and is a haven for wildlife. It's one of the most-visited national parks in the country.
• Bangor - Stephen King is one of Bangor's most famous residents, and fans can take a tour of places that have inspired his work. Maine Forest and Logging Museum give a great insight into one of the state's most significant industries. And Cole Land Transportation Museum is a great place for fans of motor vehicles.
• Baxter State Park - To start exploring the Maine Highlands, head up to North Penobscot or Mount Katahdin for hikes to suit different abilities, as well as kayaking, fishing and climbing.
• Kokadjo - You'll find more moose per square mile in the area around Kokadjo than anywhere else in Maine – head to this tiny town's Trading Post for directions.
• Greenville - Follow the scenic byway along Moosehead Lake, where you can also hike or take a boat cruise.
• Bingham - Explore the northern part of the beautiful Kennebec Valley with a detour up Route 201 towards The Forks and Moxie Falls, Maine's highest waterfall. There's also great white water rafting on the river here.
• Bigelow Preserve - Faced with the proposed development of a huge ski resort here in the 1970s, Bigelow Preserve was established to protect this undeveloped area, where you can follow the northern part of the Appalachian Trail.
• Sebago Lake - This large lake is a popular destination for boating, kayaking, swimming and hiking and fishing – it's more than 300 feet deep which creates ideal conditions for trout.

Best time to go on a road trip from Boston to Maine

It's possible to visit Maine all year round, but depending on when you travel you'll have a very different experience. You'll encounter snowfall and freezing temperatures through the winter compared to temperatures in the 80s in summer!

With summer temperatures like these, you have the perfect set-up for hiking and outdoor activities, and although the ocean never gets very warm (60 degrees Fahrenheit), you'll still see people braving the chill.

You can also join in with the celebrations at Maine's many summer events, which include Old Port Festival in Portland in June, and Maine Lobster Festival in Rockland in August.

Don't expect to have the place all to yourself if you visit in summer though - Acadia National Park is one of the most-visited in the US, and popular towns and cities can get pretty crowded in August.

Also, keep in mind that conditions can change quickly along the coastal stretch of this route. There's a chance of big thunderstorms through summer, and it rains often (though usually not heavily).

Jumping forward a few months, there's no avoiding the fact that Maine is very cold in winter. Temperatures on the coast can reach the high 30s Fahrenheit at times, but inland you should expect temperatures below freezing, and as low as 10 degrees Fahrenheit, from December to January.

However, all that snow means that Maine is all set up for winter sports. With downhill skiing in the mountains, Nordic skiing through the forests, snowmobile trails and ice fishing, Maine can be a fabulous winter destination. However, some businesses do shut up for the winter, so it pays to be flexible.

Roads are kept as clear as possible, but always drive with the freezing conditions in mind, and apply extra caution if you're used to driving in more temperate parts of the world.

Spring takes a while to warm up and can be extremely unpredictable. Melting snow can bring slushy, muddy puddles, and temperatures in March are still usually below 40 degrees. By May though, you should see warm days (up to 65 degrees) and relatively low rainfall. If you're hiking, pack bug spray, as the rising temperatures bring out bugs that, although harmless, aren't likely to enhance your day on the trail.

If you do travel in spring, check out Kenduskeag Stream Canoe Race which takes place in Bangor in April - people travel from all over the country to join in this huge event. You can also enjoy the Fiddlehead Foodie Fest in Portland, a celebration of some of Maine's culinary delights.

Fall can be spectacular, particularly in the Maine Highlands, but be aware that October sees more rainfall than any other time of year. Daytime temperatures are pleasant, from the mid-70s in September down to around 60 in October, but evenings will start to feel cold.

It is a good idea to pack a warm sweater if you're planning on visiting Harvest on the Harbor in Portland.

September also might just be the ideal time to visit – with reduced crowds, warm days, and low humidity. By November, the foliage has fallen, the weather has turned, but the snow hasn't arrived yet, so we'd suggest this is definitely a time to avoid making the trip.

Driving times and distances between Boston and Maine

To help you with your planning, we've included more details about the driving times for the places we recommend trying to fit into your route:

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Boston to Maine: 5-Day New England Fall Road Trip Itinerary

This post contains affiliate links which means that I will make a small commission if you purchase a product after clicking on any of them, at no extra cost to you.

Fall is my absolute favorite time of the year! We don’t get to experience much of the lovely fall weather in Tampa , so it always feels like the perfect time to make a trip up north. New England is one of the best (and most popular) places to road trip in the fall!

There are so many activities available during this season! Go leaf peeping in New England or do an apple cider tour in Vermont. This fall road trip will take you from Boston to Portland Maine, making stops along the way that showcase some of these unique cities and towns!

We did our New road trip at the end of October and missed peak foliage. Nonetheless, we were still able to enjoy the colors of nature. Peak foliage varies year to year so use this foliage tracker to help you plan your fall road trip.

Table of Contents

Quick links for your New England road trip

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Discover your next adventure with ease by using Viator which allows you to explore a multitude of local tours, ensuring you find the best experiences at the best prices.

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New England fall road trip itinerary

Day 1: drive from boston to maine with a pitstop in salem, massachusetts.

In order to avoid traveling from a different city or state the day our flight left from Boston, we decided it would be best to just head right to Maine and enjoy Boston on our final day. It’s just a short 2-hour drive from Boston to Maine, but first I suggest making a pitstop in Salem which is just 40 minutes outside of the city.

Salem’s historic reputation for witchcraft comes from the Salem witch trials of 1692, in which 20 people were tried and executed. Today, Salem is a tourist destination known for its Halloween celebrations, as well as its many attractions.

The city is also home to a number of historic sites, including the House of the Seven Gables, which was built in 1668. It’s one of New England’s most famous landmarks, and it’s also where Nathaniel Hawthorne set his novel “The House of the Seven Gables.”

We only had a few hours in Salem for our road trip, but fell so in love with this charming, spooky city! This may have been one of my favorite stops on our New England fall road trip.

Things to do in Salem, Massachusetts

• Take some pics at the Hocus Pocus filming locations . I mean it is a classic ! Most of the locations are pretty easy to get to, so I’d try to squeeze in a couple while you’re here. Here’s a list of where you can find all the spots.
• Visit The Witch House (The Jonathon Corwin House). It was home to Judge Jonathan Corwin (1640–1718) and is the only structure still standing in Salem with direct ties to the Salem witch trials of 1692. It’s open 7 days/week from 10 AM – 5 PM. Meaning if you have a mid-afternoon flight, this may be the first thing you want to do. Admission is $9 for adults.

• Check out the fun shops— just strolling around the downtown area is beyond pleasant. They have some super neat shops, including plenty of places to get a reading (you know I couldn’t resist!).
• Grab a bite and drink at The Roof . You’ll love this rooftop bar. We were even lucky enough to enjoy it under an eerie full moon! They have tacos, burritos, and bowls served alongside fun cocktails and shooters (or beer if you wish).
• We didn’t have the time, but if all of this hocus-pocus stuff intrigues you and you have some time to spare you can check out the Salem Witch Museum to learn more (adult admission is $16.50, and it’s open daily from 10 AM – 5 or 7 PM depending on the time of year). There are also some really interesting walking tours like the Voodoo, Vampires, and Ghosts Walking Tour or the Salem Night Walking Tour .

Once you’re done enjoying your time in Salem, head to your hotel in Portland. It’s just a little over an hour’s drive! We stayed at the Holiday Inn Portland – By the Bay .

🏨 Book your stay in Portland

With a great location in Portland, and just a short drive from Salem, Holiday Inn Portland By the Bay is the perfect place to stay in Portland!

Day 2: Portland, Maine

I’ve heard plenty of great things about Portland, and it lived up to the hype! I would love to go back to experience it during the summer months.

Portland is a diversified coastline area that welcomes guests with a variety of unique Maine experiences. You have access to it all—shopping, sailing, beaches, amazing restaurants, and more. This metropolis with a small-town feel is a cultural hotspot and a nature lovers’ paradise. It is home to craft breweries, ocean cruises, and a renowned culinary and cultural scene.

For the most part, we just took ourselves on a self-guided foodie tour and enjoyed strolling around this charming coastal city.

Things to do in Portland Maine

• Grab a cup of joe from  Bard Coffee . We were able to walk here from our hotel, and the weather was an absolute dream. The coffee was delicious! The inside wasn’t open at the time due to COVID restrictions, but it worked out because we snagged our coffee and strolled down the cobblestone streets to the next spot.

• Just a hop skip and a jump away from Bard Coffee is The Holy Donut (they have 3 locations, we went to the one on Commercial Street). This beloved local family-owned spot sells potato donuts with unique variations such as pomegranate, honey lavender, blueberry lemon, and several more! (It’s so funny to me that donuts seem to be just as much of a craze in Portland, Oregon as they are in Portland, Maine.)

• Visit Maine’s oldest lighthouse, the Portland Head Light at Fort Williams Park . With more than 90 acres of open space for enjoyment, there are options for picnics, kite flying, arboretum tours, cliffside loop walks, and exploring the rocky coastline. If you come hungry there are four food vendors (including Cousins Maine Lobster) selling lobster rolls, sandwiches, hot dogs, and gelato. The sights here were extraordinary. This ended up being my favorite thing we did in Portland!

• Grab some chowder and a lobster roll from Luke’s Lobster . You’ll love enjoying these Maine classics with stunning waterfront views. If you’re really hungry you can even order a whole steamed lobster!

• Check out some breweries and distilleries. We visited Oxbow Blending & Bottling  which offers a wide variety of draft and bottle beer from Oxbow and other guest breweries, as well as a unique collection of wine and Amaro. Next door is Hardshore Distilling where you can find some of the greatest and smoothest gin! I was shook at how good it was just to sip on, but they also can make you some fun cocktails with it if you’re not a sipper.
• Grab some frites from Duckfat which is conveniently located right outside of Oxbow Blending & Bottling. They offer a small menu that includes Belgian-style Frites that are hand-punched and twice-fried in duck fat.

Day 3: New Hampshire | Conway, Lincoln, and White Mountain National Forest

The drive from Portland to the White Mountain Forest is just a little over 2 hours. Driving through New Hampshire was an adventure on its own, we were in awe at the colors! Anything that piqued our interest we would just pull off and enjoy.

Because we had such limited time on this trip we did try to cram in as much as we could, however, I know this is only a glimpse into the many amazing fall activities to do in New Hampshire.

Things to do in New Hampshire

• Drive the Kancamagus Highway , a 34.5-mile road trip through New Hampshire’s White Mountain Forest ! The views are stunning; it’s worth taking your time here just to enjoy them. In addition to this scenic road trip route being amazing by itself, there are several points along this route where you can stop off at scenic overlooks with great photo ops.

• Lower Falls is one of the more popular scenic stops along the Kancamagus Highway. There is parking, a picnic area, and restrooms located here. During warmer months people can be found taking a dip in the watering hole.
• Just a few minutes drive separates you from the Albany Covered Bridge . The stream flowing beneath it and fall foilage surrounding it make it another amazing stop on the Kancamagus Highway.

• Eat dinner at The Common Man in Lincoln. We overstuffed ourselves, but it was worth every bite. Their Nantucket pie which includes shrimp, scallops, haddock, and Maine lobster meat baked with lobster cream sauce and seasoned Ritz crumbs gave me life.

We didn’t have time for hikes, but there are so many great ones in the area I definitely hope to have time for our next trip! Here are some popular ones along Kancamagus Highway you may want to check out:

• Diana’s Baths (1.3 miles)
• Flume Gorge (2.2-mile loop)
• Smugglers Notch State Park (several trails to choose from here)

We stayed overnight in Lincoln at the Holiday Inn Express & Suites Lincoln East – White Mountains . Holiday Inn Expresses are usually a little more affordable and always include breakfast which I love. It’s a great way to save a couple of bucks during your New England road trip.

Related read: This southeast USA road trip itinerary , Utah road trip itinerary , and Arizona road trip itinerary are three other great fall road trip options!

Day 4: Vermont | Stowe, Waterbury, and Burlington

Stowe, Waterbury, and Burlington are all great places to visit in Vermont in the fall! Stowe is a little less than 2 hours from Lincoln and has lush forests and rolling hills. A quick 20-minute drive from Stowe gets you to Waterbury which has charm, history, and beautiful valleys.

Just another 30 minutes outside of Waterbury you’ll find yourself on the eastern shoreline of Lake Champlain in Burlington, where Ben & Jerry’s originated.

Things to do in Vermont

• Drive around and admire the beauty of Stowe . Check out the Percy Farm Corn Maze . Don’t be intimidated when they make you exchange phone numbers in case you get lost. It was definitely one of the more challenging corn mazes I’ve ever done, but we made it out in a half an hour!

• Sip on cider slushies and hard cider at Cold Hollow Cider Mill in Waterbury . And of course, you can’t leave without snagging some cider donuts!

• Visit one of Vermont’s cutest gems, Burlington . Church Street Marketplace is an adorable award-winning pedestrian mall home to over 100 shops and restaurants, as well as year-round events, entertainment, and more! We enjoyed lunch at Leunig’s Bistro (the beef bourguignon was phenomenal) and drinks at Foam Brewers , Fiddlehead Brewing Company , and Shelburne Vineyard before heading to our hotel for the night.

Sometimes I reflect on how much we did in one day and it’s kind of wild. We covered three cities and didn’t feel rushed. Makes me second guess complaining there’s not enough time in the day when I can’t get 3 tasks done. We did only get just a taste of them (literally and figuratively), but I feel like what we did and saw were some of the best things to do in Vermont .

We ended up stopping at Molly’s Restaurant in Hanover and staying at Holiday Inn Express & Suites Manchester-Airport . It was 2 1/2 hours away from Burlington and less than an hour away from Boston (where we were heading the following morning).

Day 5: Boston

The final stop on our epic New England fall road trip! Boston is a pretty big city, with plenty to eat, see, and do and flooding with history. I’ve visited twice and don’t even feel like I’ve seen half of what this city has to offer yet! I’ve compiled a few of my favorite things to do in Boston, as well as some things that are still on my list!

Things to do in Boston

• Check out Beacon Hill— This is one of Boston’s most picturesque neighborhoods. The streets are lined with Federal-style and Victorian brick row houses lit by antique lanterns. Acorn Street is located here and it’s one of the most photographed streets in the city. Why you ask? It’s a charming original cobblestone street— something you don’t come across too often nowadays.
• Fenway Park— Go for a game, or just to snap a pic in front of this iconic spot. It’s the oldest of all current major league ballparks!
• Boston Public Library — The Boston Public Library is located in Copley Square, and let me tell ya it’s a stunner. If you’re like me and love a good library, it’s up there for one of the most beautiful and historic I’ve ever been to.

• Do a whale watching tour— If you are visiting Boston during whale watching season (April-October) then a whale watching tour is a must! Enjoy spotting humpback and fin whales, along with Atlantic white-sided dolphins from your high-speed catamaran.
• Freedom Trail — One of Boston’s most iconic things to do! Follow 2.5-mile Freedom Trail that leads to 16 nationally significant historic sites including Paul Revere House (the oldest remaining structure in downtown Boston), Boston Common (America’s oldest public park), Old State House (the oldest surviving public building in Boston), the Old North Church (if you have time, tour the crypt!) and several other historical locations. If you want to get the most out of your experience, they offer affordable guided tours !
• Prudential Center — Enjoy shopping and eating at this gorgeous enclosed shopping center. I especially recommend checking out Eataly! Copley Place is another stunning shopping center located right next door.
• Visit Cambridge— Wander Harvards’ campus, eat and play trivia at The Asgard, or check out one of their fun speakeasies A4cade (located in a grilled cheese shop and full of games) or Brick and Mortar (we actually really struggled to find this one!).

If you want to explore the city in a unique way check out Boston Duck Boat Sightseeing City Tour . You get to tour the city in a renovated World War II amphibious vehicle. The tour begins on the streets and then is taken to the Charles River for a view of the city by boat.

🚌 Hop-On Hop-Off Trolley Tour

If you want a tour that allows you to get off and enjoy some of the stops while also receiving historical info and fun facts check out this 14-stop tour is for you.

Where to eat and drink in Boston

Here are some of my favorite bars and restaurants we got to experience in Boston!

• VERSUS — a super fun arcade bar!

• Citrus and Salt — a Baja-inspired restaurant with Mexican eats and fun, creative cocktails.

• Terra at Eataly—delight yourself with amazing Italian food and craft cocktails in this stunning eatery.

• Legal Sea Foods — best (ok, and only) whole lobster I’ve ever had! It was so unbelievably good, one of the best parts of it is the shrimp & scallop stuffing it was filled with. Also, let’s take a moment to admire all of the lobster in the lobster bisque. They have several locations throughout Boston.

• Trident Booksellers & Cafe —This place is so cozy and especially nice on one of Boston’s dreary days. Come here for good coffee and a good breakfast, and leave with a new book!

We didn’t get to check it out, but the Samual Adams Brewery is located in Boston too!

Are you ready to experience this epic Boston to Maine New England fall road trip?!

If you are looking for a road trip to do in the fall, New England is one of the best. From Boston to Portland, Maine and each stop in between has so much to offer. From beautiful views of rivers, falls, and mountains to great food and fun activities. I hope this post has given you some ideas for your epic fall road trip!

Destiny Snyder is a passionate travel blogger and content creator based in the Tampa Bay area. Originally from a small town near Toledo, Ohio, Destiny's love for exploring new places began when she moved to Florida in 2017. She enjoys uncovering hidden gems, sharing insider tips on the best things to do, places to eat, and coffee shops to visit in every destination. With her blog Guided by Destiny and niche sites Sunkissed in Tampa and Sunkissed in St. Pete, Destiny aims to make trip planning stress-free and fun for her readers.

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If I follow this itinerary what states am I staying in what nights ? Thank you .

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Boston To Maine Road Trip Itinerary (2-3 Days)

• By TripMemos Team
• April 29, 2024
• In USA Travel

When Boston traffic snarls to a stop, you may be thinking: road trip. It's time to escape the big city life for the beauty of Maine. Keep reading for an easy 2-3-day road trip that will restore your soul.

On this 2-3-day-Boston to Maine road trip, you will see Penobscot Bay from the top of Mount Battie in Camden, sail out of Boothbay Harbor, and enjoy the gorgeous views from a historic inn. You will soak in the beauty at the Coastal Maine Botanical Gardens and stroll the Marginal Way with its spectacular ocean views and white sand beaches in Ogunquit.

Traveling this Boston to Maine Road Trip will cover 400 miles. You will be transported into the rocky wonder of "The Pine State" Maine. Keep reading for options for a 2-3-day trip with things to see, places to stay, and good food to enjoy.

How Long is the Trip from Boston to Maine?

The Maine southern border community of Kittery sits 67 miles from Boston. Take I-95 North 48 miles to the New Hamshire border past the town of Seabrook, New Hampshire. Kittery is only 19 more miles north on I-95. Camden, Maine sits 105 miles north of Kittery for a total of 191 miles from Boston.

Where Should We Stop between Boston and Maine?

Your Maine road trip should include some of the historic and scenic harborfront sea towns of Maine. For this road trip, you will drive out to Camden by freeway, then take local roads back south to Boston. You will get to explore Camden, Boothbay, and Ogunquit, Maine. 

Should We Visit Acadia National Park in Bar Harbor?

Acadia National Park near Bar Harbor, Maine should be on everyone's bucket list. The National Parks Service lists Acadia as the 8th most popular national park with over 3.3 million visitors a year. Acadia, with its spectacular mountains and flowing water, deserves its own separate weekend road trip.

Start the Boston to Maine Road Trip with Camden, Maine

What's the best time to leave on a road trip.

You and your road-tripping friends/family should decide together when is the best time to begin your road trip. If you leave Friday night after work, you can have more time to see the sights. If you leave first thing Saturday morning, you can save money on the hotel. It is purely a personal decision.

First Stop Camden, Maine

Whether you leave Boston Friday night or early Saturday morning, head to Camden, Maine. You will drive 191 miles up I-95 and US-1 to Camden.

Camden began as a shipbuilding town named after Charles Pratt, the first Earl of Camden (England), in 1791. Today Camden is a scenic seaside town with great inns, delicious seafood restaurants, with a picturesque waterfront for strolling.  

Picnic in Camden Hills State Park

Begin the fun part of the road trip with a picnic in Camden Hills State Park. Pick up some deli sandwiches and a lobster roll (if you've got a cooler) at the Camden Deli . You can hike, bike, cross-country ski, and camp inside a park.

The Sights from Mount Battie

Camden Hills State Park's premier sight is the top of Mount Battie in the southern section of the park. You can drive to the top of Mount Battie on Mount Battie Road.

Many prefer to hike to the top instead. You can take the 2.4-mile Carriage Trail which winds through splendid forests to the top. Or you can challenge the rocks themselves on the moderate to strenuous 750-foot climb on the Mount Battie Trail. 

Great Hikes in Camden Hills State Park

Take the mile-long moderate hike on the Megunticook Trail up to Ocean's Lookout where you can look down on the cars in the parking lot on Mount Battie. Head to the western part of the park to hike the mile-long Maiden Cliff Trail that winds 800 feet about Lake Megunticook

Downtown Camden, Maine

After exploring Camden Hills State Park, drive into Camden for a relaxing stroll downtown. See the High Street Historic District with 50+ homes and inns from the 19th century. Many have beautiful gardens to enjoy.

Find a great casual restaurant for an early dinner. Head to Sea Dog Brewing for great local beers, burgers, and nachos. For a delicious farm-to-table dinner, head to Blaze Camden for burgers and wood-fired pizza.

Drive South to Boothbay Harbor 

After dinner in Camden, the road trip continues with a short 90-minute (61 miles) drive down the coast to Boothbay Harbor for the night.

Boothbay Harbor has long been a deep port harbor with a strong connection to fishing, lobstering, and sport boating. Locals refer to Boothbay Harbor as "The Boating Capital of New England" for its many marinas and yacht clubs. 

Great Inns of Boothbay Harbor

Before leaving on your Boston to Maine Road Trip, make a reservation in Boothbay Harbor at one of their many beautiful inns.

You could choose a 19th-century sea captain's home at the Bayside Inn with its waterfront views and a short walk to town. During the warmer seasons, you could enjoy a resort experience with a pool and beach at the Smugglers' Cove Oceanfront Inn.  

Remember to check all websites to see what is open year round and what is only open seasonally.

Sailing on Boothbay Harbor

Your road trip won't be complete without a sail on the bay. Reserve with Eastwind Schooner  to enjoy a fully-crewed charter. For the more adventurous take sailing lessons with Midcoast Sailing to see the open water with a sheet (rope) in your hand and to stand at the helm (wheel) guiding the sailboat.

Lunch in Boothbay Harbor

After a great morning on the water, sit at the picnic tables at Shannon's Unshelled , "Fresh from Trap to Table,"  for some of the best lobster and french fries at this walk-up joint. Another great lunch spot is the relaxed bar Brady's with all types of seafood, burgers, and comfort food—Maine Pot Roast! 

Coastal Maine Botanical Gardens

From Boothbay Harbor, head inland for 4 miles to see the wonderful gardens of the Coastal Maine Botanical Gardens.

Wander through over 300 acres of flower gardens, a children's garden, a hillside garden, and more. Visit the Native Butterfly and Moth House to sit and be soothed by the colorful residents as they alight on you looking for nectar.

The 2-Day Boston to Maine Road Trip

Let the Coastal Maine Botanical Gardens be your final activity if you are on a 2-day Boston to Maine road trip. Head south for 2 hours (94 miles) for a final dinner in the quaint sea town of Ogunquit, Maine. After dinner, you've got just 72 more miles of freeway driving back home to Boston.

Great Dinners in Ogunquit, Maine

Head to The Front Porch in Ogunquit, for three dining experiences: the main dining room, the bar+lounge, or the lively sing-along piano bar.

Another fun option is freshly all made-in-house ingredients for New York-style pizza at Lapizzeria . Or head to dinner at That Place in Ogunquit for delicious steaks and seafood dishes in a lively bar atmosphere.

The 3-Day Boston to Maine Road Trip

If you are lucky enough to do a 3-Day Boston to Maine Road Trip, spend your last day in Ogunquit, Maine. You can stay in a historic B&B like The Trellis House or a beautiful inn like the Nellie Littlefield Inn & Spa or the Gazebo Inn with its swimming pool and spa.

Great Brunch in Ogunquit, Maine

On the last day of your road trip, sleep in then head out for brunch done right. Try the Egg and I Pancake and Waffle House or The Greenery Cafe for the full brunch experience of eggs, hash, french toast and so much more. For coffee and freshly made croissants or pastries, head over to Mornings in Paris for a taste of Europe.

The Marginal Way in Ogunquit, Maine

The "high" point of any visit to Ogunquit is strolling the cliffside paved walkway above the beaches and rocky shore on the Marginal Way . This 1.5-mile trail passes historic homes and scenic inns. You will have amazing views from all sides.

Small parking lots are available at each end. You may find street parking easier as there are many accesses to the trail. Benches are scattered along the way for looking down at the ocean. Sturdy stairs bring you down to the different beaches.

Perkins Cove in Ogunquit, Maine

Conclude your 3-Day Boston to Maine road trip with the picturesque Perkins Cove . This former artist colony now includes great restaurants, shopping, art galleries, and scenic overlooks.

Perkins Cove sits on a peninsula with the ocean on one side and the cove on the other. A beautiful white pedestrian, stroller, and bicycle drawbridge connect Perkins Cove to downtown Ogunquit.  

The 2-3 Boston to Maine road trip has barely scratched the surface of all that the Pine State has to offer. As you explore, take the time to stop to see something that catches your eye. Share your road trip finds in the comment section below.

Boston is awesome, but Maine is calling you.

Check out these other awesome road trips:

Four Best Road Trips from Florida to Other States

5-Day Colorado Road Trip Itinerary

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From boston to maine: the ultimate 3-day new england road trip itinerary.

Boston to Portland Maine Road Trip Map

Click on the image of the map below to open an interactive version in google maps with information on the drive from boston to portland, maine (and beyond) and maine getaway points of interest., new england road trip stop #1: newburyport massachusetts, new england road trip stop #2: portsmouth, new hampshire, new england road trip stop #3: kittery, maine and around, new england road trip stop #4: lunch in wells, maine, new england road trip stop #5: kennebunkport, main, new england road trip stop #6: biddeford, maine, new england road trip stop #7: portland, maine, things to do in portland maine , rwanda bean, portland head lighthouse.

Maine's Craft Beer Scene

"Beauty is in the eye of the beerholder"

Walk Portland

Dinner at david's restaurant, new england road trip stop #8: l.l. bean factory store, new england road trip stop #9: bowdoin college and around, new england road trip stop #10: maine maritime museum, new england road trip stop #11: land's end, new england road trip stop #12: giant's stairs trail, new england road trip stop #13: island candy company, new england road trip stop #14: potts point.

New England Road Trip Stop #15: Bath, Maine

Where to stay on a boston to maine road trip.

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Boston to Maine Road Trip: Your Complete Itinerary Guide

America is hallowed ground when it comes to road trips. Ever since Kerouac published On the Road , the thought of driving around this amazing country has been on everyone’s minds. Whether you want to explore Hawaiian islands or drive from coast to coast, there are endless wonders to be discovered. One option you might be considering is a Boston to Maine road trip.

This is a relatively short trip but also among the most epic. America’s northeastern coast holds spectacular beauty that can be enjoyed at any time of year. Before you set off, though, it’s important to do your research. Make sure you know what to expect, what to pack, how long you need, and where to stop.

This article will help you make your Boston to Maine road trip as epic as possible. Keep reading to increase your understanding of this region. Learn how to prepare for an epic road trip in America’s northeastern states.

Table of Contents

Why Take a Boston to Maine Road Trip?

The Great American Road Trip is hallowed ground for the traveler. It’s the ultimate expression of freedom and exploration. America is a vast patch of land that requires time to fully understand. That’s why many people choose to rent or buy a car and then journey across different parts of the country. Rather than staying in a single destination, you can get to know this land better by taking to the road.

The question is, which route do you take? Route 66 is perhaps the most famous but at almost 2500 miles (almost 4000 km) in length, this isn’t feasible for most people. Instead, it’s better to choose a shorter route that can be accomplished more quickly. A Boston to Maine road trip is closer to 250 miles, making it doable in a single day. If you’re pushed for time, then this is the perfect way to get all the benefits of a road trip, without spending a lot of money or taking loads of time off work.

Different parts of America offer different benefits for tourists. Yellowstone National Park might be the most beautiful area of the country while southern states might contain more fascinating indigenous history. If you’re into the founding of this great nation, though, then it all begins in the northeast. That’s where Europeans first arrived to found the USA as we know it today. A Boston to Maine road trip is the best way to discover the history of America while traveling through stunning scenery.

How Far is a Boston to Maine Road Trip?

Every road trip will be unique, meaning that the distance you travel will vary. It will vary depending on which part of Boston you start from, where specifically in Maine you end up, which route you take, which sights you want to see, and how far you deviate from the original route. This can drastically alter the total journey time of your trip.

If your plan is to leave central Boston and drive directly to a town in central Maine like Guilford, then your road trip will be a little under 250 miles (400 km). However, most road trippers won’t take such a direct route. Road trips aren’t about getting to a place as quickly as possible. They’re about experiencing and enjoying the journey along the way. They’re about unexpected obstacles and spontaneous detours.

Therefore, it’s best to assume your route will be longer than this. Sit down with a map (either physical or online) and plot the route you want to take. This is the easiest way to see how long the distance really is. The chances are that your total driving journey will be more like 300 to 400 miles (480 – 640 km) long. You’ll then want to add a bit on to account for detours you make along the way.

How Long Does this Road Trip Take?

Like the distance, the time it takes you to complete this journey depends on a number of factors. If you wanted to, you could easily complete the journey in under half a day. After all, the journey time between Boston and Guilford, Maine, is under four hours. You could easily do it in one sitting, without taking any breaks. But what kind of a road trip would that be?

Most people who make this journey want to take their time. They want to stop at beauty spots and historical monuments . They want to get out of the car every now and then to explore this fantastic bit of land. Perhaps you want to stop to eat. Also, you’ll be unlikely to take the quickest route between the start and the end of your Boston to Maine road trip.

Once you’ve added in detours and stoppages, this road trip is likely to take longer than a day. We recommend staying overnight at least once along the way, turning this into a two-day drive, perhaps over the weekend. However, it’s impossible to know exactly how long your journey will take. The point of road trips is that they’re spontaneous and you decide when to stop and when to drive as you go, based on a gut feeling. You’ll only know how long this trip will take once it’s done.

Key Stops to Make

In order to plan your trip, you need to decide exactly where to stop along the way. These are the key sights that make the trip worth taking. Fortunately, there is plenty to experience along the route from Boston to Maine. The important thing is to decide whether you want to visit natural beauty spots, historical monuments, big cities, or a mixture of all three.

Once you leave Boston, the main urban areas of interest include Newbury Port, Salisbury, Hampton, Portsmouth, York, Portland, Brunswick, and Waterville. There are even more towns further north, depending on how far into Maine you travel. As the names of the towns imply, these were founded by the English as soon as they arrived in the New World. That makes them excellent places to learn about the founding of America.

In terms of natural beauty, you’ll want to stay near the coast for glimpses across the great Atlantic Ocean. The biggest and most beautiful national reserves include Wells National Estuarine Research Reserve and Rachel Carson National Wildlife Refuge. Both of these places are must-visits if you love nature. In terms of monuments, lookout for historical homes, lighthouses, and observatories along the way.

Road Trip Packing Guide

The Boston to Maine road trip involves traveling through some of America’s coldest destinations so be prepared for this. If you’re from the south, then you probably don’t realize just how cold it can get up there. In Boston – the southernmost point on this road trip – winter temperatures can drop as low as 40°F (-5°C). In this case, you’ll obviously need warm clothes to keep you warm throughout the trip.

Furthermore, the cold brings snow, which you need to be prepared for. Ensure your car is fitted with snow tires and always carry a shovel to dig yourself out of trouble. You should also make sure that your car is always fully stocked with plenty of food and water so you know you’ll be okay if you get stuck.

Of course, you could always make the trip during the summer. In this case, it’ll be much less dangerous and you won’t need to pack so much survival gear. The good thing about this trip – compared to, say, an Arizona desert road trip – is that you’ll never be too far from a town. That means you can pack light and always buy more gear if you need it.

Things to Do When You Get to Maine

Your Boston to Maine road trip doesn’t need to end once you reach your final destination. If you’re going to Maine anyway, make sure you have a list of things to do once you get there. This is the perfect chance to round off your trip and end it on a high. With that in mind, research the best things to do in Maine. You can pick your favorite to be your final destination.

What are your favorite things to do? Love American food ? Eat in Maine’s best restaurants. Prefer culture? Visit all the museums. This is your unique itinerary so it’s up to you to do the research and plan the best adventure. However, to get your creative juices flowing here are some of the best things to do in Maine:

• Explore Acadia National Park
• Take a trip out to Monhegan Island
• Marvel at the Victoria Mansion in Portland
• Wander through the Portland Museum of Art
• Learn history at the Maine Maritime Museum
• Have a look around the Nubble Lighthouse
• Relax on Old Orchard Beach

Maine is full of incredible beauty and fascinating history. A road trip gives you the freedom to explore it at your own pace, prioritizing the things that excite you the most. Make sure you choose something to end your Boston to Maine road trip and use it as motivation to keep on chewing up the miles.

For more than 11 years, Joe has worked as a freelance travel writer. His writing and explorations have brought him to various locations, including the colonial towns of Mexico, the bustling chowks of Mumbai, and the majestic Southern Alps of New Zealand. When he's not crafting his next epic blog post on the top Greek islands or French ski resorts, he can often be found engaging in his top two hobbies of surfing and hiking.

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12 Fantastic Stops On A Road Trip From Boston, Massachusetts To Bangor, Maine

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Boston is the perfect city to begin this scenic New England seacoast trip. The booming Seaport District, luxury shopping in the Prudential Center, or places to explore Boston’s historic past are all just minutes from Logan International Airport. The busy airport offers a convenient spot to begin your Boston to Bangor road trip. Finish up your adventure in Bangor, a friendly and walkable city. It is home to author Stephen King and local nature-focused experiences that are a nod to Maine’s great forests. 

With a fun rental, maybe a Jeep with a fold-back soft-top or a classic Mustang convertible, you will be off in search of amazing coastal cuisine, unique shopping experiences, perfectly curated craft brews, and coastal fun-in-the-sun adventures.

Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.

1. Boston, Massachusetts

Shopping at the airy Prudential Center , home to high-end brands, is a feast for the fashionista’s eyes. You can find L’occitane, Swarovski, Oakley, and more that will satisfy your desire to own pretty things. When you need to stop for a bite, try Earls Kitchen & Bar or Eataly , both globally well-known establishments. 

History buffs will need to experience Boston’s Freedom Trail . Another great option for exploring the city is the Boston Duck Boat Tour , a unique land and water tour.

Boston is home to many classic, well-known craft breweries. Check out our list of 5 Fantastic Breweries To Visit In Boston to help you decide which one or two you want to visit while you are in town.

Start your trip with a Boston luxury stay. There are a wide selection of great options. The Marriott Vacation Club Pulse is in the renovated historic Custom House. They offer well-appointed suites with panoramic views of the city.

2. Newburyport, Massachusetts

As you begin your trek north, stop for lunch at Bob Lobster in Newburyport. There is always a line filled with hungry locals and visitors, but it moves quickly. Their selection of lobster rolls are fresh and tasty. 

Take a walk around the beach at Plum Island or the Parker River National Wildlife Refuge to experience a coastal habitat for over 300 species of birds and wildlife. 

For more information about visiting beautiful Newburyport, check out How To Spend A Perfect Day In Quaint Newburyport .

3. Hampton Beach, New Hampshire

New Hampshire’s coastline is relatively short when compared to their northern and southern neighbors. However, they jam a tremendous amount of beachy fun in a little package. Hampton Beach is a classic East Coast beach, where aromas of fried food, suntan lotion, and salty air morph together in the quintessential “day at the beach” memory.

The water is chilly, but the beach is wide with a walkway and parking along its length. Hampton Beach is the spot for your road trip beach day.

Get the most out of your Hampton Beach visit with links to all the around town happenings in How To Spend A Perfect Day In Quaint Hampton Beach .

4. Portsmouth, New Hampshire

Portsmouth is a lovely stop along the way to wander through quaint shops, small bistros, and artist galleries. 

Portsmouth Brewery is an anchor in Portsmouth’s bar and restaurant scene. Order a flight to sample a variety of their craft brews at this fun lunch or dinner spot. 

Another great stop is the Salt Cellar , where you can find a wide variety of finishing salts. Try the Black Lava Sea Salt, Lime Citrus Sea Salt, Merlot Wine Sea Salt, and others. They will add the perfect four-star touch to your home-cooked delicacies. 

5. York, Maine

More beachy fun awaits you in York, Maine. Short Sands, York’s main sandy beach, is located in the heart of the action. The beach area offers parking and a busy downtown district with shops and restaurants. Long Sands Beach is another popular York beach. It has sections of rocks to scramble over and a sandy beach area along with on-street parking.

A must-see shop is the Stonewall Kitchen Company Store . Every Stonewall product you love, but can never find at home, is here just for you. Additionally, they offer cooking classes in their onsite kitchen.

6. Portland, Maine

Portland is a seaport city full of history, foodies, and fun. You can spend lots of time wandering the Old Port district exploring wonderful restaurants and quaint shops.

Red Soxs fans will want to take in a game and watch the Portland Sea Dogs . You never know what up-and-coming baseball phenom or rehabbing all-star may take the field.

One must-stop is The Holy Donut . Their mashed potato donuts are making baked goods history. Dine on pomegranate, maple bacon, and sea salt donuts made with fresh Maine potatoes. Sweet treats with healthier ingredients and their daily rotation of flavors will amaze and delight you. 

7. Freeport, Maine

Freeport is home to the L.L. Bean Flagship Store , which is really more like a compound with separate buildings including the Hunting and Fishing Store; Bike, Boat, and Ski Store; Home Store; and the Outlet Store. For the L.L. Bean enthusiast, it is possible to spend an entire day exploring. 

When you are finished shopping, stop at Stars & Stripes Brewing Company and enjoy a fresh craft beer while you ogle over your shopping purchases. 

You can easily spend an entire day in Freeport. How To Spend A Fantastic Day In Freeport, Maine: Shopping, Eating, And Relaxing is full of tips for getting the most out of your visit.

8. Bath, Maine

Bath’s Main Street is an artisan haven. Beautiful historic buildings filled with shops carrying items from Maine’s artists and crafters contribute to the bohemian vibe. 

Stop at Bath Sweet Shoppe for a mid-day, sweet treat. A bag of milk chocolate gold coins or Jelly Belly Red Raspberry Hearts evokes fond childhood memories. 

9. Wiscasset, Maine

Enjoy a leisurely afternoon in historic Wiscasset. Visit the Nickels-Sortwell House , the 1812 Jail , and the Castle Tucker home for a peek into the lives and times of the people of coastal Maine.

Enjoy an al fresco lunch from the legendary Red’s Eats . The line gets particularly long during traditional dining hours, but queueing up for a mid-afternoon meal means less waiting time. 

10. Camden, Maine

Camden’s charming waterfront downtown area is blessed with picture-perfect views. Sailboats grace the snug harbor, which is lined with local restaurants offering on-the-water dining views. 

Maine is known for its lobster, and you won’t find a better lobster roll than at McLoon’s Lobster Shack located on Spruce Head Island. Tucked away in a classic Maine cove is a small red shack that serves up amazing seafood. It is worth the drive; your reward is a beautiful view and a perfectly prepared lobster.

If you have extra time to stay over in Camden, you will find great ideas in How To Spend A Beautiful Weekend In Quaint Camden, Maine . 

11. Belfast, Maine

Belfast is a charming town that rises from the waterfront to a thriving shopping area. The waterfront is busy with fishing and leisure boats making their way out to Penobscot Bay. 

Visit Eat More Cheese to kit out your picnic basket, then grab a bench and enjoy the waterfront views. 

12. Bangor, Maine

Bangor has a cozy, hometown feel wrapped in a sophisticated city that only Mainers can seem to accomplish. A hub for big-name concerts and great food, the hometown of Stephen King, and close to forested wonderment, Bangor is unique.

Waterfront Concerts presents concerts from nine of Bangor’s concert venues. With guests like Thomas Rhett, Jay Leno, Brothers Osborne, Kiss, and others, you can plan your visit around a fun waterfront venue or cozy auditorium.

For Stephen King fans, SK Tours will treat you to a fascinating 3-hour tour of locations that inspired King’s “Derry, Maine,” filming locations, and a view of his private residence. Your guide will enchant you with local tales, and the history of the King family and their many philanthropic contributions to the Bangor area. 

Spend some time hiking and canoeing at Hirundo Wildlife Refuge just outside of Bangor. With 7 miles of hiking trails and peaceful streams, you will find the perfect spot to satisfy your need for nature and a Zen-like moment.

Fine dining couldn’t be finer than at Novio’s . The bistro is tucked away on a side street where those in the know go to dine on sumptuously prepared and gorgeously plated cuisine. The menu changes seasonally and is focused on the restaurant’s own garden-grown produce and locally-sourced proteins. The ramp fritters are a light and flavorful starter. Follow up with the crab pistou with house-made linguini and delicately dressed with a white wine creme fraiche. Save room for dessert, you’ll want to savor the s’mores cheesecake.

Pro Tip: The drive up Routes 1 and 1A offer beautiful coastal scenery and bucolic farmland views. If you are not flying out of Bangor you can head back to Boston on Interstate 95 for a faster, albeit less scenic drive.

Sandi loves writing about culture, cuisine, adult beverages, cruising, golf, skiing, road trips, hiking, New England, and photography. Traveling solo, with hubby Chris, or the entire Barrett clan there is always a story waiting to be told.

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Must-See Stops on a Boston to Bar Harbor Road Trip

Posted by Liz Dengler August 09, 2021 Updated June 08, 2023

Maine is arguably the best place to spend your vacation time on the East Coast, with remote and rugged landscapes, numerous farms and ranches, old historic towns, lighthouses, and stunning swaths of coastline.

It’s easy to understand why some people take one trip to Maine and start daydreaming about moving north to live the quintessential New England life. Fortunately, if you’re in Boston, the Boston to Bar Harbor road trip is an easy drive, not to mention a beautiful one.

Here’s the best itinerary for your Boston to Bar Harbor road trip, complete with the best stops for travelers interested in small coastal towns, history, wildlands, beauty, and true New England hospitality.

Related Read:   When is the Best Time to Visit Acadia National Park?

Boston to Bar Harbor By Segment

There are two routes you could take for a Boston to Bar Harbor trip, but if you have time, travel along the coast the entire way. Technically fewer miles (275 versus 285), it does take a little more time (about 5.5 hours instead of 4.75) but is totally worth it.

The trip along the coast is one everyone should do at least once. Visiting the quaint coastal New England towns, enjoying views of the rocky shores, and taking advantage of the numerous opportunities to get out and explore trails or historical sites all make this route well worth the extra time.

If you can, take a few days to make your way along each segment of this trip.

Related Read:   11 Relaxing Swimming Holes in New Hampshire

Segment 1: Boston, MA to Portland, ME

• Distance: 112 miles
• Drive time without stops: 1 hour, 45 mins

For simplicity’s sake, this road trip guide assumes you’ve already explored Boston to your heart’s content and are ready to explore beyond the lands “just outside Boston.” T

his first segment will take you through New Hampshire and into Maine.

Related Read:   The 6 Best Scenic Byways to Fully Experience Massachusetts

Segment 1 Highlight: Portsmouth, NH

When you get to Portsmouth, NH, make sure to stop and explore the town. Fuller Gardens , just south of the city on the coast, is a botanical garden open to the public. The Gardens have a fascinating history dating back to 1927, and the Rose Garden is a must-see.

Your next stop in Portsmouth should be the Seacoast Science Center . This educational detour is located in Odiorne Point State Park . Learn about the oceans and marine life and explore tide pool habitats. You can also sign up for kayak tours, workshops, and family programs, to name a few of many. This is a great first stop to get everyone excited about fun things to come.

Related read : 8 Unique Places to Stay Near Boston When You Need to Get Away

Segment 1 Highlight: Portland, ME

Now here is a city worthy of exploration. Portland, is a fast-growing city on the ocean. The downtown, also called Old Port , is home to all sorts of charming shops and restaurants and sits along the waterfront. You won’t regret taking extra time to spend a day or two in this little city.

Portland Head Lighthouse is always breathtaking. Built in 1791, it’s the oldest lighthouse in Maine and is still active today. However, it now houses a museum about the cape’s history.

If you have the time, look into taking a sail on one of the Portland Schooner Company’s windjammers that leave from quite near downtown. They have several special events through the season, or you can book a standard two-hour public sail .

Related Read:   12 Magical & Unique Places to Stay in Maine

Segment 1 Side Trip: The Crane Estate

About a 30-minute detour from the interstate, the Crane Estate is a great side trip for hiking fans, history buffs, or those fascinated with architecture. The estate began its life as a humble farm in the late 1900s; however, through the preservation efforts of The Trustees , the property was developed into an expansive historic site now open to the public.

The estate has several zones: Castle Hill , Crane Beach , and the Crane Wildlife Refuge . There are historic houses, collections, beaches and trails to explore, and sometimes special events on the weekends. Be sure to pick up a map when you enter.

Segment 1: Where to Stay

You’ll find no shortage of charming B&Bs in either of these towns. At the Crane Estate, you can stay at Lodging the Inn at Castle Hill , a beautiful estate turned inn is rich with history. In Portland, you can check out some of these cute airbnbs or try the beautiful (and pet-friendly)  Inn by the Sea .

If you can’t pull yourself away from Portsmouth, try the downtown Ale House Inn or glam Wentworth by the Sea . Portland has plenty of camping , too.

Segment 2: Portland to Rockland

• Distance: 79 miles
• Drive time without stops: 1 hour, 40 mins

The coastal stretch from Portland to Rockland has so much to do that it’s impossible to recommend everything. The 79-mile stretch of road (92 if you add Popham Beach) is jam-packed with small towns, beach visits, and lighthouses.

The following are only a few suggestions to get you started, but you could easily spend a week exploring everything this segment has to offer. While this is one of the best days on a Boston-to-Bar-Harbor road trip, it also works well as its own separate trip for a few days if you want to see everything in more detail.

Segment 2 Highlight: Freeport

Freeport is undoubtedly a tourist town and is probably best known by out-of-towners for the legendary Flagship L.L. Bean outlet stores. But Freeport has more to offer than just shopping.

You can lace up your boots and explore any of the numerous nearby parks and preserves that offer up great hiking, or grab your binoculars and visit the Mast Landing Audubon Sanctuary , a birding hotspot just a mile from downtown. History buffs in your crew may want to check out the Freeport Historical Society.

Segment 2 Highlight: Rockland

Rockland is directly on the Boston to Bar Harbor main route and is a beautiful stop. There are a couple of lighthouses in the harbor worth visiting. Start at Owls Head Light, located in Owls Head State Park , dating to 1852. It’s a pleasant spot to spend an afternoon picnicking and exploring. On your way from Owls Head to the second lighthouse, stop by the Maine Lighthouse Museum to learn about maritime history and the lifesaving evolution of lighthouses along the coast.

The second lighthouse to check out is the Rockland Breakwater Lighthouse . Placed at the end of the breakwater to guide ships into the harbor, visitors can walk the entire length of the breakwater. Wear comfortable shoes, though, as the lighthouse is almost a mile out to sea.

Segment 2 Side Trip: Popham Beach

Only a 25-minute detour from the coastal route, Popham Beach State Park is a must-visit stop on the Boston to Bar Harbor road trip year-round. The ocean views are stunning, and the beach is amazing to explore; sand dollars and shells are common if you keep your eyes peeled.

If the tide is low, you can walk out to the largest of the Fox Islands, but beware of the changing tides. You don’t want to be stuck out away from the shore when the tide comes in and covers the path back to the coast.

Segment 2: Where to Stay

Along this segment, there are a plethora of campgrounds, especially around Freeport .

In Rockland, you can choose between a short-term rental, hotel, or even splurge on a bed and breakfast, such as the LimeRock Inn . Maine Forest Yurts is a fun choice, too.

Segment 3: Rockland to Bar Harbor

• Distance: 85 miles
• Drive time without stops: 2 hours

At last, you’re almost there! Much like the segment before, this stretch has plenty of quaint New England coastal towns to visit along the 85-mile stretch of road. Camden and Belfast are both great towns to explore. However, as you move north of Belfast, the route becomes a bit more remote and scenic.

There are still places to visit, but it’s as if the road knows that you don’t want any distractions on the way to your destination: Bar Harbor.

Segment 3 Highlight: Acadia National Park

Hardly a contest, the main attraction near Bar Harbor is Acadia National Park. From bathing on Sand Beach to hiking Cadillac Mountain to biking the extensive carriage trails network, Acadia itself is deserving of a weeklong trip.

Be sure to explore all of the best hikes in the park and hit up all the highlights along the Park Loop Road.

Related Read:   8 Spectacular Glamping Spots Near Acadia National Park, Maine

Segment 3 Highlight: Bar Harbor

Naturally, if you made it all the way here, you must take a bit of time to explore the hospitable town of Bar Harbor . Tuck into one of the small shops to find your souvenirs or head out to one of the many delicious restaurants — the Thirsty Whale has a great menu packed full of coastal favorites.

After some food, head out for a stroll along the Shore Path to take in sites of the harbor or out to Bar Beach. There’s also a trail (accessible only during low tide) that heads to the top of Bar Island.

Related read : T op 10 Campgrounds to Book for Your Visit to Acadia National Park

Segment 3 Highlight: Wildlife Cruises

The Bar Harbor Whale Watching Company offers all manner of on-the-water activities, from whale watching tours to a puffin and lighthouse cruise. Whale watching trips are between three and five hours, and after 30 years, the company has a good sense of where the whales will be, offering you the best opportunity to see the whales up close.

If you’re looking for a slightly shorter trip, the puffin and lighthouse cruises are an excellent opportunity to see all kinds of wildlife while touring the lighthouses. Make sure to bring your binoculars to see the wildlife in their full glory.

Segment 3 Highlight: Schooner Sail

If you’re into boating, set aside some time in Maine to sail on a schooner. The Downeast Windjammer Cruise Lines offers an assortment of opportunities, from morning sails to sunset cruises.

The evening sails can be romantic and fun as they serve wine and beer on board and often have live folk music on board for entertainment. The afternoon sail is a great option as it comes with a narration on local history and wildlife. The trips aren’t too much of a detour from Bar Harbor – the pier is about 15 minutes north of town.

Segment 3 Where to Stay

Bar Harbor is home to one of the country’s most popular national parks and you’ll have a huge assortment of lodging options.

Check out the beautiful airbnbs  nearby, stay at a yurt and wellness center or spring for the downright stunning Terramor Outdoor Resort . If you want to stay in Acadia National Park , though, you should make sure to book well in advance.

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Posted by Liz Dengler

Liz is a freelance writer and editor who lives on the road. Literally. Home is a cozy van parked wherever the views are stunning and the data is adequate. Always exploring, wherever she ends up, you can be sure she will be out hiking, biking, skiing, and paragliding.

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Boston to Portland, Maine: A Road Trip Itinerary (2023-2024)

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Are you looking for a fun and scenic road trip along the New England coast? If so, consider making the journey from Boston to Portland, Maine . It’s not a long road trip, but this scenic route takes you through charming coastal towns and offers plenty of opportunities for adventure, exploration, and fresh caught seafood, if that’s your jam!

To help you plan your Boston to Portland trip, we’ve put together a New England itinerary that highlights some of the best stops along the way. From Boston, Massachusetts to Portland, Maine, this coastal New England road trip offers a variety of suggestions for where to stop and what to do to make this a very memorable trip!

Table of Contents

How to Get from Boston MA to Portland ME

Do you know that you can easily take a train from Boston, Massachusetts to Portland, Maine?  The Amtrak Downeaster connects Boston and Portland, so if you’d like to skip the driving and just ride direct, that’s not a bad option at all. Amtrak trains can be a very convenient way to road trip, but you will of course miss out on all the fun stops along the way.

However, if you’re looking to get from Boston to Portland, Maine in just a couple of hours without having to slide behind the wheel of your car, you’ve got options. Check out the train schedule here . There are multiple Amtrak trains per day leaving from Boston North Station heading to Portland!

If you’d rather fly than ride, Logan Airport has plenty of flights from Boston to Portland, Maine, too! Jet Blue, American Airlines, Delta, and more fly daily between these two locations. Click here to look for deals on Boston to Portland ME flights !

If you’re the type of person who would prefer to control where you stop and for how long, drive. There is a direct route that takes you up I-95 that would get you from Boston to Portland ME in just under 2 hours, but that’s not for people looking for road trip adventures along the way.

Want the road trip experience but don’t have your own wheels? Click here to find deals on a rental car !

How Far is it from Boston to Portland, Maine?

Not very! Whether you’re traveling by plane, train, or automobile, it’s just about a couple of hours, but if you’re looking to enjoy some of the top sights in coastal Massachusetts and Maine, then it will take a couple of days at least to really get the full experience.

Can you do the drive in one day with quick stops at each spot? Technically, yes. But spreading this coastal road trip between Boston and Portland out over a weekend or longer will be more fun! 

We are including the best things to do at each stop between Boston and Portland and letting you decide where to spend your time during this very customizable coastal road trip.

We suggest allowing 2-3 days for this Boston to Portland ME trip, but you should personalize it any way you’d like. We’re even including our favorite places to stay along the way for overnight fun, too.

Where to Stop on the Drive from Boston to Portland, Maine

Stop 1: salem ma (20.2 miles via us-1n).

Kick off your trip by heading north from Boston to Salem, Massachusetts. Salem is a fascinating town with a rich history, and is worthy of being its own vacation destination, especially if you’re planning an October trip and looking for haunted places to visit and stay ! 

Salem is one of our favorite places to visit and it’s definitely worth a longer visit to take advantage of all the cool ghost and walking tours , but if you’ve only got a few hours to spend in Salem during your Boston to Portland road trip, these are our suggestions for what to see and where to stop:

• Hocus Pocus Filming Locations
• See the Salem Witch House
• Pay your respects at Salem Witch Memorial
• Grab a bite and/or a brew (coffee or beer!) at Gulu Gulu Cafe 

Where to Stay: Hotel Salem

Stop 2: Rockport MA (20.1 miles via MA-128 N)

Next up is Rockport, Massachusetts! Technically, this stop does take you just a bit off the relatively straight path north to Portland, but this charming coastal Massachusetts town is worth the detour, I promise. 

We have loved every visit we’ve made to this gem by the sea; it’s one of those quaint coastal places where you’ll find delicious restaurants, great breakfast spots , unique things to do, and even cool places to stay if you decide to do an overnight. These are our top recommendations for what to do in Rockport:

• Go strolling down and shop Bearskin Neck
• See Motif #1
• Enjoy a lobster roll at Roy Moore Lobster Co

Where to Stay: Emerson Inn

Stop 3: Hampton Beach in Hampton NH (36.9 miles via MA-133 W)

One of the most iconic beaches in New England , Hampton Beach is a definite must-visit if you’re taking a scenic road trip from Boston to Portland ME! In fact, it landed on Country Living’s list of the top eight “classic beach boardwalks” in the US, with the magazine citing the many offerings of Hampton Beach as being a perfect representation of classic summer nostalgia.

Of course, it’s true! Not only is there the beautiful beach with its picturesque boardwalk, but there’s also a lot of non beach fun nearby, like playing arcade games at Funarama, gambling a little at Ocean Gaming Casino, eating some yummy fried seafood, and then heading to Buc’s Lagoon Mini Golf and Ice Cream to play a round and follow up with a frozen treat!

Some must-dos while in Hampton Beach:

• Walk the Hampton Beach boardwalk
• Squish your toes in the soft sand at Hampton Beach State Park!
• Have some fun at Funarama

Where to Stay: Ashworth by the Sea

Stop 4: Portsmouth NH (13.6 miles via NH-1A N/Ocean Blvd)

Portsmouth is one of the top spots to visit on the New Hampshire Seacoast, and should not be missed on your road trip from Boston to Portland, Maine! Portsmouth has plenty of places to stretch your legs, with Strawbery Banke Museum, the historical outdoor museum, and the very walkable downtown with cobblestone streets and lots of great shopping- yay sales tax-free New Hampshire!

If you’re looking for a great place to grab a bite in Portsmouth, there are two notable spots to consider: Fezziwig’s Food & Fountain and Portsmouth Book & Bar . The former is a delightfully whimsical cafe that is perfect for a sandwich, pastries, and tea, and the latter is a bookstore/restaurant/bar that really delivers on all fronts! Both are memorable places to visit and eat in Portsmouth, but there are lots of cool breweries, bars , and breakfast spots to check out too!

Where to go on your Portsmouth stop:

• Enjoy living history at Strawberry Banke Museum
• Stroll pretty Prescott Park (you might even catch a summer concert!)
• Take advantage of no sales tax shopping!
• Grab a bite at Fezziwig’s

Where to Stay: The Hotel Portsmouth

Stop 5: York ME (10 miles via 95 N)

Once you’ve had your Portsmouth fun, head north to York, Maine. One of the coolest coastal towns in Maine, York is known for its beautiful beaches and historic sites and would be a fantastic stop on your Boston to Portland trip.

There’s plenty of great eye candy in York, with Long Sands Beach and Nubble Lighthouse; head to Sohier Park and you’ll have fantastic views of the lighthouse. For history lovers, the Old York Historical Society has impeccably maintained several historic structures, including the Old Gaol , originally built in 1656 as Maine’s first jail.

If you’re hungry in York, you’ve got options, but Fox’s Lobster House has been serving up fresh caught lobster and the finest blueberry pie since 1966, so they’re the place to go for a taste of quintessential coastal Maine!

These are some of the top things to do during your stop in York:

• Walk Long Sands Beach
• Ooh and ahh and photograph Nubble Lighthouse
• Visit the Old Gaol
• Eat at Fox’s Lobster House

Where to Stay: York Harbor Inn

Stop 6: Ogunquit ME (10 miles via US-1 N)

Next stop is Ogunquit, Maine, whose name means Beautiful Place by the Sea in the Algonquin language. This charming coastal town has lots to do and see , including scenic Marginal Way trail, which offers stunning views of the coastline, and lovely beaches that are perfect for sunbathing. 

Visit Perkins Cove, take a walk along the beach (Footbridge Beach is especially picturesque), or visit the Ogunquit Museum of American Art. The Ogunquit Playhouse has been a staple of this area since 1933, so if you can make the time, seeing a show at this iconic spot would be a memory-making activity, for sure. Pair this with a dinner at The Front Porch , the local piano bar/restaurant, and you’d be in for a great evening out in Ogunquit.

These are some of our top recommendations for your Ogunquit stop:

• Stroll Marginal Way
• Enjoy the scenery at Footbridge Beach
• Dine at The Front Porch
• Catch a show at the Ogunquit Playhouse

Where to Stay: Gorges Grant Hotel

Stop 7: Kennebunkport ME (11.7 miles via US-1 N and State Rte 9 E)

Onwards to charming Kennebunkport, Maine . This coastal Maine town is known for its historic homes, quaint shops, and beautiful beaches; a drive by the iconic Wedding Cake House (private property so keep a respectful distance) will confirm! 

Kennebunkport is full of great places to eat and shop, and heading to Dock Square will take you to many of them! This unique waterside area is home to several popular places to visit in Kennebunkport, and the Boathouse Restaurant is one of the most popular local restaurants that offer waterfront dining! 

What to do during your Kennebunkport stop:

• Drive by the Wedding Cake House
• Stroll and shop Dock Square
• Indulge a little at Boathouse Restaurant

Where to Stay: The Boathouse (yes, it’s also a lovely waterfront boutique hotel, too!)

Stop 8: Old Orchard Beach ME (18.2 miles via US-1 N to 95 N)

Next up is Old Orchard Beach, Maine, home to the last remaining beachfront amusement park in New England! Palace Playland has classic arcade games and amusement park rides, including a ferris wheel, roller coasters, and so much more, plus you’ve got beautiful Old Orchard Beach with its 7 miles of sandy beach to enjoy, too.

Another popular OOB attraction is the Old Orchard Beach Pier , home to all kinds of great places to eat, drink, shop, and enjoy that spectacular ocean scenery! Hungry? Grab a bite at Hooligan’s Steak & Ale, the first restaurant you’ll see when walking onto the OOB Pier! 

Must-do’s for your Old Orchard Beach stop:

• Play at Palace Playland
• Walk Old Orchard Beach
• Grab a bite at Hooligan’s on the Pier

Where to Stay: Alouette Beach Resort

Stop 9: Cape Elizabeth ME (17.1 miles via US-1 N)

The next stop on this Boston to Portland ME itinerary is Cape Elizabeth, home to some of the prettiest lighthouses in Maine . Granted, you’re just a few miles outside of Portland at this point, but skipping over a visit to the lighthouses in this lovely spot would be a travesty!

There’s Portland Head Light, the oldest remaining lighthouse in the state, Ram Island Ledge Lighthouse, and Two Lights, Cape Elizabeth Light and its twin, which is now a private residence. Cape Elizabeth is home to beautiful beaches, parks, and one of the best restaurants in Maine : The Lobster Shack at Two Lights.

Things to see in Cape Elizabeth:

• Tour Portland Head Light
• See Cape Elizabeth Light
• Eat at The Lobster Shack

Where to Stay in Cape Elizabeth: Inn by the Sea

Stop 10: Portland ME (8.5 miles via ME-77 N)

Finally, your destination is at hand! You’ve arrived in beautiful Portland, one of the top vacation destinations in Maine, and a town that seems to truly have something for just about everyone . You’ve got museums and art galleries, fun out on the water , shopping and browsing through Old Port, the Portland Observatory , and breweries, bakeries , breakfast spots , coffee shops, and restaurants galore to choose from.

In fact, if you’re a seafood lover, you’re going to LOVE the options you have for seafood in Portland! Check out Luke’s Lobster Shack on the Portland Pier for waterfront dining.

Portland has several great options for where to stay, including conveniently located vacation rentals and hotels , and beautiful boutique hotels that offer a variety of unique experiences, like the Press Hotel , located in the former headquarters of the Portland Press Herald. 

Whether you’re spending a weekend or a day in Portland, you’ll find fun in this popular Maine city by the sea.

What to do in Portland, Maine:

• Stroll Old Port
• Get out on the water
• Tour the Portland Observatory
• Eat some lobstah

Where to Stay in Portland: The Press Hotel

There are many different ways you can choose to get from Boston to Portland, Maine, but if you take the scenic route along the coast, you’ll have so many fantastic memory making opportunities! Coastal New England road trips are the best!

You might also like:

• Ultimate Boston to Acadia National Park Road Trip (2+ Day Itinerary)
• 5 Spectacular Maine Road Trip Routes You Won’t Want to Miss!
• New England Fall Road Trip: 8 Great Itineraries (+Bonus Ideas)
• The Ultimate Maine Coast Road Trip: Kittery to Bar Harbor

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The Perfect Coastal Maine Road Trip

Laura Itzkowitz is a freelance writer and editor based in Rome. She has been contributing to Travel + Leisure since 2014, when she started as a fact checker before becoming a contributing digital editor in 2015 and going freelance in 2016. She has also held positions as a contributing editor at The Points Guy and the NYC cities editor at DuJour Magazine. In addition to Travel + Leisure , her writing has appeared in Architectural Digest , Surface Magazine , Brooklyn Magazine , T Magazine , The Wall Street Journal , Vogue, GQ, Departures, Afar, Fodor's, Town & Country , Condé Nast Traveler , Robb Report , Hemispheres, and others. When she's not jetsetting around Italy and beyond, she can be found in Rome, enjoying some cacio e pepe or relaxing at home with her husband and two dogs. Originally from the Boston area, Laura moved to New York City in 2011 to pursue a master's degree in creative writing and translation at Columbia University. She also holds a bachelor's degree in French from Smith College. * 10+ years of experience writing and editing * Co-wrote "New York: Hidden Bars & Restaurants," an award-winning guide to New York City's speakeasy scene published by Jonglez Editions in 2015 * Contributed to "Fodor's Brooklyn," published by Penguin Random House in 2015, which won silver in the Lowell Thomas Travel Journalism competition * Contributed an essay to "Epic Hikes of Europe," published by Lonely Planet in 2021 * Updated the 2022 edition of "Fodor's Essential Italy"

Lobster shacks , waves crashing against rocky outcroppings, pine trees, and rugged bluffs— Maine is New England’s crowning gem. And with winding roads overlooking the Atlantic, secluded lighthouses, and charming cities up and down the coast, it's a gem best experienced by car.Here now, the best places to eat, drink, shop, and sightsee between Portland and Bar Harbor.

2 p.m.: Shopping in Portland’s Old Port District

At just over an hour-long flight from New York City or a two-hour drive from Boston, Maine ’s largest metropolis is a great place to start. Take a leisurely walk around the harbor and Old Port, where historic brick buildings house restaurants, bars, and shops. Start by the harbor on Commercial Street and work your way up Exchange Street, which is lined with boutiques selling everything from clothes and jewelry to locally crafted pottery and fudge.

7 p.m.: Dinner at Eventide Oyster Co., Portland

Come for bivalves on the half shell, and stay for Korean-style fried oyster buns. These guys take their shellfish seriously, but not too seriously to play with the conventions of Maine’s regional cuisine. Last year we named Eventide one of America’s best oyster bars and it’s still worth a visit.

9 p.m.: Check in to the Press Hotel, Portland

Spend the night at the quirky new Press Hotel , an Autograph Collection Hotel, which opened in May in the Old Port. Design firm Stonehill & Taylor took inspiration from the building’s heritage as the former home of the Portland Press Herald . You’ll find playful journalism motifs peppered throughout, from the lobby installation made of antique typewriters to the custom wallpaper printed with headlines chosen by the newspaper’s editors. Each of the 110 rooms channels a 1920s writer’s office. Sitting at the vintage-inspired desk, you might feel compelled to send a postcard home.

9 a.m.: Breakfast at the Standard Baking Company, Portland

In the morning, head toward the harbor for pastries at Portland’s must-visit artisanal bakery , which has been using locally grown, organic ingredients in their excellent baked goods for the past twenty years. The croissants, brioche, and morning buns are equally delicious. Grab some sweets to save for later—their financiers and chocolate chip cookies are the best around.

10 a.m.: Portland Head Lighthouse, Cape Elizabeth

Take a slight detour to see the historic lighthouse on Cape Elizabeth, about 20 minutes south of downtown Portland. Abutting flowering fields above a rocky coastline, this classic landmark is Maine’s oldest lighthouse. George Washington commissioned it and the Marquis de Lafayette dedicated it in 1791. The Victorian Keeper’s house now serves as a museum displaying lenses and interactive exhibits.

12:30 p.m.: Archer’s on the Pier, Rockland

Depart Portland and start making your way north to Rockland. After the two-hour drive, you’ll probably be hungry. Snag a waterfront table at Archer’s on the Pier , where you can watch the boats sail by. You can’t go wrong with a classic lobster roll served with hand-cut fries and coleslaw, though chef and owner Lynn Archer is best known for her King of Clubs sandwich made with lobster, bacon, lettuce, and tomato, which won the prize in Bobby Flay’s Throwdown.

2 p.m.: Farnsworth Art Museum, Rockland

Dedicated to showcasing Maine’s role in American art, the must-see Farnsworth Art Museum comprises a modern building, the Wyeth Center, the historic Farnsworth Homestead, the Olson House, and a gallery for young artists. The main building features paintings by Andrew Wyeth, George Bellows, Milton Avery, and Alex Katz, as well as sculptures by Robert Indiana. A whole room of canvases depicting ships at sea and other coastal imagery pays homage to the region and the ways it has inspired artists for centuries. Peruse the galleries in the former church up the street to see works by three generations of Wyeth painters. If you have time, take a tour of the Farnsworth Homestead, which sheds light on its 19th-century inhabitant, Lucy Farnsworth, the museum’s original benefactor.

6 p.m.: Downeast Windjammer Sunset Cruise, Bar Harbor

Drive along scenic route 1 overlooking Penobscot Bay as you continue north toward Bar Harbor. You might be tempted to stop in the boutiques that line the main streets of this seaside city, but make sure to arrive at the pier in time to board the Downeast windjammer ’s sunset cruise. You might be asked to help raise the sails on the four-mast vessel, then enjoy a relaxing ride around picturesque Frenchman’s Bay, which is dotted by forested islands. Bring your own wine or beer and a warm jacket—even in summer, it gets chilly on the water.

8:00 p.m.: Jordan Pond House, Mount Desert Island

Once you’re back on dry land, head into Acadia National Park for dinner at the Jordan Pond House. The only restaurant within the park, this place is renowned for its popovers, which go very well with the lobster stew. Dinner is served inside, but if you’d like to dine outside on the lawn with a view of Jordan Pond and its distinctively sloped hills, come back for lunch or afternoon tea.

9:30 p.m.: Mount Desert Island Ice Cream, Bar Harbor

If you have room for desert—and you definitely should—head back into Bar Harbor for a cone at this creative creamery. Blueberry ice cream may be common in these parts, but Mount Desert Island Ice Cream churns one-of-a-kind flavors you won’t find anywhere else. For something subtle and refreshing, try the basil ice cream, which pairs well with a scoop of fig.

10 p.m.: Asticou Inn, Northeast Harbor

Spend the night at the cozy Asticou Inn on Mount Desert Island. This historic property dates back to 1883 and served as a home away from home for the early 20th-century affluent set that summered in Bar Harbor. The inn’s 48 rooms feature classic décor like floral wallpaper and dainty white curtains and come equipped with free WiFi. In the morning, you can go for a swim in the heated pool or play tennis and enjoy a leisurely brunch of lobster eggs benedict on the terrace.

10 a.m.: Acadia National Park, Mount Desert Island

You could spend days exploring Maine’s only national park , which comprises 35,000 acres of trails, pine-studded mountains with scenic overlooks, and beaches on Mount Desert Island. As soon as you enter this vast, gorgeous landscape, you’ll understand why prominent Americans like John D. Rockefeller Jr. and Brooke Astor vacationed here throughout the 20th century. (Rockefeller built the carriage roads that traverse the park.) Climb (or drive) to the summit of Cadillac Mountain for panoramic views of Frenchman’s Bay. Hike around Jordan Pond and the Bubbles, where the trail leads you along a wooded path and rocky outcroppings on the pond’s perimeter. Don’t miss Sand Beach, Thunder Hole, where waves crash violently against the rocks, and of course, the Bass Harbor Head lighthouse.

4 p.m.: Atlantic Brewing Co., Bar Harbor

Make your way to the northern point of Mount Desert Island for a free tour and tasting at the Atlantic Brewing Company . Set on a ten-acre farm, this excellent craft brewery focuses exclusively on ales. Learn about the brewing process as you stand among the vats of beer, then taste a flight of their classic and seasonal brews, which run the gamut from light and crisp to rich and dark. The blueberry ale has subtle notes of the ubiquitous berry, but the true standouts are the Bar Harbor Real Ale and the Cole Porter.

6 p.m.: Union River Lobster Pot, Ellsworth

Keep heading north for dinner at this no-frills seafood restaurant in nearby Ellsworth. Don’t expect anything fancy, just classic Maine dishes prepared exactly right. Lobsters are boiled in saltwater and served with drawn butter, French fries, coleslaw, and homemade bread. The fisherman’s platter arrives with a generous portion of fried scallops, clams, shrimp, and fish. Wash it down with Atlantic Brewing Company ale and finish with a slice of blueberry pie.

New England Wanderlust

Connecticut , Fall , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  June 7, 2023

The PERFECT New England Fall Road Trip Itinerary: 3, 5, 7, 10 & 12 Day Options! (2024)

There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done quite a few fall foliage road trips and even more fall getaways. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience.

This post details the best places to visit in New England during fall foliage season that are worth the hype, the best times to plan your road trip, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.

This itinerary is also geared toward first-timers and those looking to find the best foliage spots . If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading 😉

During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!

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Tips For Planning A Trip To New England In The Fall

There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉

The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later . For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.

If you’re planning a bucket list 2-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important.

I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!

Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.

Also, book in advance . I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.

Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2022 road trip, I barely had service through much of New Hampshire and Vermont. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.

Lastly, prepare to pay . Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best 😉

What Is The Best Time To Visit New England For Fall Color?

In a nutshell, the last week of September, or the first week of October. However, it does vary depending on where you’re heading.

As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.

The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.

Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.

The greater Boston area, and Connecticut will peak mid-late October, depending on the year.

How Many Days Do You Need In New England In The Fall?

The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 12 day road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.

If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.

If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.

The great thing about the best places for fall foliage are located in some of the smallest states, so you can cover a lot of ground in a short amount of time.

Best Places To See On A New England Fall Road Trip

While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best spots, I recommend sticking to Maine , Massachusetts , New Hampshire and Vermont . And flying into Boston.

Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.

Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.

I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.

If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut , which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.

If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!

If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see .

Some Things To Know About My Itineraries

They all begin in Boston , assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed.

They’re done in true road trip style , meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!

I give you options! Of course, I stand by all my suggestions ☺️ However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.

10 Day New England Fall Road Trip Itinerary From Boston

Okay, let’s get into my perfect New England fall road trip itinerary options! We’re beginning with my suggestions for an incredible 10 day adventure.

10 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Explore Boston Or Take A Day Trip To Salem Day 3-4 : Bar Harbor/Acadia National Park + An Optional Stop In Salem Day 5 : Jackson, NH Day 6 : Franconia, NH (Driving The Famous Kancamagus Highway To Get There!) Days 7-8 : Stowe & Woodstock, VT Day 9 : The Berkshires and/or Litchfield, CT Day 10 : Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT

Breakdown Of The 10 Day Itinerary Option

Day 1: Arrival In Boston Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!

Where To Stay In Boston:

• Luxury : The Langham
• Splurge : Boston Harbor Hotel
• Moderate : Revere Boston Common

Pro Tip On Fall Foliage In Boston : Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.

Day 2: Explore Boston

Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:

• Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
• Newbury Street for shopping
• The North End for history and food
• Beacon Hill for charming cobblestoned streets at the famous Acorn Street
• Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!

Click here to check out my post on the best Boston food tours!

Day 2: Optional Day Trip To Salem

If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.

Salem is an easy day trip from Boston without a car because of this convenient ferry! Click here to check out the Boston → Salem Ferry!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: Drive To Bar Harbor & Acadia National Park

Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.

This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.

But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂

Bar Harbor is the town adjacent to Acadia National Park , and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!

Where To Stay In Bar Harbor:

• Bayview Hotel . An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
• Bar Harbor Villager Motel . Clean, updated and spacious. Also, walkable to everything in town.
• Little Fig Hotel . A cute, modern boutique hotel walkable to town.

Here are some posts that will help you further plan this portion of your trip:

• Best Stops To Make Driving Boston To Portland, Maine
• Best Stops To Make Driving Portland to Acadia National Park
• The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)
• Best Time To Visit Acadia National Park

Day 4: Explore Acadia National Park

Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:

If you’re up for it , starting your day with sunrise at the top of Cadillac Mountain is always incredible! It’s one of the first places in the U.S. to see the sunrise, depending on the time of year, and starting October 7 through March, it’s the very first spot in the country to see the sun come up. This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.

Next, head to the Jesup Path scenic walk , which is especially beautiful in the fall season.

Then, park at the Sand Beach parking lot , and walk the Ocean Path for incredible views . This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!

For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.

Continue on Park Loop Road to Jordan Pond House for lunch , and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.

For more foliage views, hike the Bubble Rock Trail after lunch.

Day 5: Drive To Jackson, NH + Spend The Night

Without stops, this drive takes about 4 hours and 15 minutes.

One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford , ME . It’s got a very cool outdoor setting, and they have fantastic craft beer.

I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂

Here are some fun fall things to check out in Jackson:

• The Cog : This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park , which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
• Honeymoon Covered Bridge & Flossie’s General Store
• Glen Ellis Falls
• The cute town of North Conway

Where To Stay In Jackson:

• Christmas Farm Inn (this place is super cozy!)
• The Inn At Thorn Hill & Spa

Option To Stay In North Conway : North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!

Here are some fun things to check out in North Conway if you choose to visit:

• Cathedral Ledge Distillery
• Ledge Brewing Company (between North Conway and Jackson, technically)
• The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
• North Conway Scenic Railroad

Day 6 – Drive The Kancamagus Highway To Franconia, NH

The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.

For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.

Tips For Driving The Kanc:

• Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
• There are no bathrooms or gas stations on the drive, so plan accordingly.
• The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
• During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.

Pro Tip : Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍

Stops To Make On The Kanc (in order from Conway to Woodstock):

• Albany Covered Bridge
• Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
• Sabbaday Falls
• Sugar Hill Scenic Overlook
• CL Graham Wangan Overlook
• Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
• Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.

🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive – Click here to check out this audio tour!

There are also tons of hiking trails along The Kanc , so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.

After The Kanc, your next stop is Franconia Notch State Park . And this is where most of the top things to do are , especially in the fall season .

Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.

Not sure if this is right for your itinerary? Click here to check out my detailed post in if Flume Gorge is worth visiting , and everything you need to know to plan the perfect visit.

Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.

If you have time to explore more of Franconia Notch State Park, I also recommend these activities:

• Cannon Mountain Aerial Tramway
• Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
• The views at Echo Lake Beach

Where To Stay Near Franconia:

• Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
• Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
• Woodstock Inn & Brewery – Cozy inn with a brewery.

Here are some posts to help you plan this portion of your trip:

• Fun Things To Do In Franconia, NH
• Fun Things To Do In Littleton, NH
• Fun Things To Do In Lincoln, NH
• Where To Stay In New Hampshire In The Fall
• Where To Stay In The White Mountains: Guide To The Towns

Day 7 – Drive To Stowe Or Woodstock, VT

Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.

Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.

The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia , and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.

If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.

Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.

The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.

Where To Stay In Stowe :

• The Green Mountain Inn . It’s located right on Main Street, so you can walk to a lot of places.
• Spruce Peak Resort . Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.

Where To Stay In Woodstock :

• The Woodstock Inn & Resort . It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
• 506 Inn On The River . Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉

Here are some posts that will help you plan your time in Stowe and Woodstock:

• Best Things To Do In Stowe
• Best Things To Do In Woodstock

Day 8 – Explore Stowe & Woodstock, VT

Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town .

Best Things To Do In Stowe :

• Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
• Drive Smugglers Notch for amazing foliage.
• Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
• Visit Emily’s Covered Bridge, and learn about it’s spooky history.
• Sample the hard cider at Stowe Cider.
• Sip on craft brews at Alchemist Brewing (one of my favorites in New England).

Best Things To Do In Woodstock:

• Stroll through the charming downtown shops and eateries.
• Pop into Mon Vert Café for a warm drink.
• Snap a photo with Middle Covered Bridge in town.
• Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
• Visit Billings Farm & Museum.
• Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.

Day 9 – Drive To The Berkshires Or Litchfield, CT

Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.

The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.

Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe .

The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.

Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.

During this drive, these are the best stops to make:

• The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
• Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
• Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
• Walk through the charming town of Lenox.
• Stroll through quaint Stockbridge, too!
• Snap photos with the covered bridge in Sheffield.

Where To Stay In The Berkshires:

• The Red Lion Inn . A historic and famous inn in the heart of Stockbridge.
• The Dewey . A cozy, traditional New England B&B in Lenox.

The other option is to drive to Litchfield, CT , which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.

How To Spend Your Time In Litchfield Hill, CT:

Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.

• Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
• Continue to follow Route 7 to New Milford. The drive is very scenic!
• Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
• Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
• End in the charming town of Litchfield.

Where To Stay In The Litchfield Hills : Litchfield Inn . Refined and still very cozy, and one of the best in the area!

Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂

I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.

Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way

If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.

How to spend your time in Sturbridge, MA :

• Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
• Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
• Sip on craft beer at Altruist Brewing Company.

And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.

But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂

Optional Adjustments For The 10 Day Itinerary:

• You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
• If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!

12 Day Road Trip Itinerary Option

If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:

Option 1 : Add in 1 day to see Litchfield, CT after The Berkshires . Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.

Option 2 : Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.

Option 3 : Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads .

Burlington & Shelburne, Vermont things to check out :

• First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
• In Burlington, check out the waterfront area, and walk along Lake Champlain.
• Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
• The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
• Church Street Marketplace in Burlington is a must!
• In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.

Vermont back roads driving itinerary near Stowe :

This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂

• The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
• Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
• The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
• Peacham is a very small town with iconic landscapes and scenery.
• Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
• The drive between all these destinations will also be lovely and scenic, and packed with fall color.

1 Week (7 Day) New England Fall Road Trip Itinerary

If you have 7 days, welcome to your itinerary! This option is the same as the 10 day option, but eliminates Acadia National Park to save time.

7 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Drive To Jackson, NH + A Stop In Salem, MA Day 3 : Drive To Franconia Along The Kancamagus Highway Days 4-5 : Drive To Stowe or Woodstock, VT + Stay 2 Nights Day 6 : The Berkshires Day 7 : Return To Boston

For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.

5 Day New England Fall Road Trip Itinerary

With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.

Option 1 : Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.

Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.

With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season .

Option 2 : Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.

Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.

Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.

Option 3 : Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.

Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.

I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! 😂), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.

3 Day New England Fall Road Trip Itinerary

3 days in New England is the perfect long weekend getaway!

With 3 days, I suggest you stay in one location , and add day trips . If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.

Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.

It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.

Weekend New England Fall Road Trip Itinerary

For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.

Vermont Fall Road Trip Itinerary

Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)

For a Vermont fall road trip , you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less. A popular route to take in Vermont is Route 100 , which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.

For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.

Day 1 : Bennington & Manchester Day 2 : Drive to Woodstock, stopping in Grafton and Weston on the way Day 3 : Spend the day in Woodstock Day 4 : Drive to Stowe, stopping in Montpelier if you’d like Day 5 : Spend the day in Stowe Day 6 : Staying in Stowe, take a day trip to Burlington & Shelburne Day 7 : Drive back

Day 1 Suggestions : Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:

• The Bennington Battle Monument for fall foliage scenery.
• Downtown Bennington for shopping on Main Street (small, but cute!).
• Apple Barn is a few minutes from Main Street for a fun country store and bakery.
• Zoe’s in Manchester for lunch (great sandwiches!)
• Downtown Manchester for shopping in a cute town (don’t skip Northshire!)

Day 2 Suggestions : Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.

For the rest of the itinerary, refer to the 10 day option for details 🙂

Click here to check out my post on a Vermont covered bridges road trip!

New Hampshire Fall Road Trip Itinerary

My second favorite fall foliage destination! Here’s my suggested itinerary for a New Hampshire-only fall road trip.

To just see New Hampshire , you can also spend anywhere from 4-7 days.

With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days , but adjust as you need to!

Day 1 : Portsmouth Day 2 : Lake Winnipesaukee Days 3-4 : Littleton/Franconia Days 5-6 : North Conway/Jackson Day 7 : Drive back

Connecticut Fall Road Trip Itinerary Option

If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!

As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.

The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.

The best towns to stay in in the Litchfield Hills region are:

• New Milford
• Washington/Washington Depot

Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.

If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.

What To Pack For A New England Fall Road Trip

I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like . And keep checking it until the day before you leave .

This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland 😉 But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.

Here are some things I recommend you consider when packing for a fall road trip through New England:

Waterproof hiking boots . If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here . They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild !

Good hiking socks to keep your feet dry . An awesome brand to support is Tarn Tough Socks , which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!

Waterproof rain jacket to stay dry if it rains . You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely water proof ( not water-resistant).

Layers . The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.

Jeans . These work really well for most days. Fall in New England is pretty casual.

Hiking clothing . For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂

Comfortable sneakers or boots . When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.

Dinner outfits . New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.

Reusable water bottle . You’ll need to stay hydrated while out exploring!

Day pack . If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.

Does It Snow In New England In The Fall?

Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip.

How Do To A New England Fall Trip On A Budget

So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.

Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet 😉 Here are my tips:

• Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus in exploring outdoors, I stay in motels with efficiency kitchens . You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
• Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
• Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
• Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.

Is Fall In New England Worth It?

A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.

More posts you may enjoy:

• Fall In New England: The Best Things To See & Do
• Vermont In The Fall: Festive Things To Do!
• Fall In New Hampshire: The Best Things To Do
• Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
• The Best 7 Day New England Road Trip Itinerary For Any Season
• Best Stops To Make On A Boston To Stowe, VT Road Trip
• Vermont vs. New Hampshire In The Fall
• Maine In October: Best Towns For Foliage & Things To Do!
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Awesome Corn Mazes In Vermont
• Best Time To Visit New England
• Best Time To Visit Vermont

That’s A Wrap On The Best New England Fall Road Trip Itinerary

And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!

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New England Fall Road Trip Itinerary: 10 Stunning Stops

by Mark and Kristen Morgan

Published: August 23, 2021

There are many places in the world you can see leaves turn in Autumn, but they pale in comparison to one famed and celebrated region in the US northeast where science, nature and climate combine to put on an extraordinary light show each year. We are of course talking about fabled New England and we’re going to show you 10 places you can’t miss when planning your New England fall foliage road trip, with 5 day itinerary, 7 day itinerary and 10 day itinerary examples included to help you nail down the best possible route for your trip.

We will use our first hand experiences from road tripping New England in fall to bring you tips, advice and unmissable stops to take on your visit. This is one of those true bucket list USA road trip experiences in which it pays to be organized, plan effectively and make the most of every day.

So, let’s get stuck into those 10 unmissable stops and planning your perfect New England fall foliage road trip itinerary!

The Science Behind Fall Colors

What do we know about the changing of colors to give ourselves the best chance of being in the right place at the right time?

Well, we know that fall colors peak furthest north and work southward through the latitudes. So for example, the Blue Ridge Parkway in Virginia and North Carolina is gorgeous in fall, but the colors won’t change there until much later in the season.

Also, we know elevation plays an important role in when peak colors will be on display. Colors will change first in mountainous regions of Maine, New Hampshire and Vermont before they do at lower elevations.

But the most important aspects are weather conditions leading into Autumn, and amount of daylight. It all starts way back in Spring! A late Spring or intense Summer drought can potentially delay peak fall colors by a week or two.

Conditions Affecting Predictions For Peak Fall Colors

In addition to elevation, latitude and weather conditions before fall, there are more specific conditions that can affect peak fall once we actually reach Autumn:

• Soil moisture levels
• Amount of sunlight during the day
• Length of night
• Day and night temperature (important)

So what would constitute as perfect conditions for the best chance at ‘peak’ fall colors being their most radiant and predictable?

• Wet and warm Spring conditions
• Summer without drought or unusually high / low temperatures
• Warm Autumn days and cool but not freezing nights

And what causes the colors to change once conditions are right?

Sunlight pumps leaves full of chlorophyll during Spring and Summer. Once daylight wanes in Autumn, so does the amount of chlorophyll.

That leaves room for other pigments in the leaves, such as anthocyanin and carotenoids to shine.

Why Focus On VT, NH, ME and Even NY

The region of New England technically contains 6 states; Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire and Vermont. In fall, this entire region transforms into an adventure playground for leaf-peeping lovers and passionate photographers.

However, there are three New England states among the six that we feel just have to be prioritized for the very best scenery and most radiant colors; New Hampshire, Maine and in particular Vermont.

But we’re also going to throw a curve ball by including a region not technically part of New England (gasp!) … New York’s Adirondack Mountains are a stone’s throw from the border with Vermont and the colors are just as special.

We want you to see the best places in New England when you take your fall road trip, but we would prefer you to see the best colors. That means skipping the likes of Boston, Portland and Providence on this particular visit to the northeast.

They’re all awesome places and we visited them all on our New England road trip in fall. But they don’t have the colors of rural Vermont and New Hampshire, plus we had days to spare.

Here’s why you should focus on the northern parts of New England for a fall foliage road trip:

Vermont’s rolling hills are overflowing with charming rural towns, barns and covered bridges. But the state is 80% covered in forest and that can only mean one thing; spectacular fall foliage everywhere you look.

Further Reading: The best places to visit in Vermont

New Hampshire

New Hampshire mixes excellent hiking options in stunning mountainous areas with staggeringly beautiful fall foliage colors.

It also has one of the best mini road trip routes in New England during fall – the Kancamagus Highway.

Maine is huge. It is much bigger than the other New England states and that means it’s hard to fit most of the northern parts in to your road trip. Unless you have more than 2 weeks of course.

However, Acadia National Park is one of the very best places you can visit in all of New England in fall so if you have the spare time, it’s hard to skip.

New York’s Adirondack Mountains, including Winter olympic town Lake Placid and its surroundings are beautiful in Autumn. The popular mountainous region is incredibly popular thanks to a host of activities and of course glorious foliage colors.

When Should You Plan Your New England Road Trip For Peak Fall Colors?

It is impossible to plan the perfect ‘peak’ fall road trip itinerary in New England. You would need to be in many places at the same time for that to be possible. We’re not quite there, yet!

Historically, the last 2 weeks of September and the first 2 weeks of October are when the colors change. So that would put October 1st in the middle of that and therefore a ‘peak’ fall foliage target.

Science tells us that colors change in the North and at elevation first, eventually working South and to lower levels.

We’ll get into example itineraries below, but here are some rough dates to use for each itinerary time frame working North to South:

• 5 Day New England Fall Road Trip – We would suggest aiming for September 29 through October 3.
• 7 Day New England Fall Road Trip – Add a day either side, so September 28 through October 4.
• 10 Day New England Fall Road Trip – Add a day before and two after, so September 27 through October 6.
• 14 Day New England Fall Road Trip – Add a day before and three after, so September 26 through October 9.

Should You Book Your Trip In Advance?

Here are two scenarios:

• You don’t book in advance and keep an eye on live fall foliage updates to guarantee hitting peak fall. This also means you have flexibility on bad weather days. However, there are very limited hotels available and those that do have rooms will be more expensive.
• You plan and book your whole trip in advance, getting good value in hotels and can relax. But there’s a chance you won’t time it just right and you will have to deal with whatever weather comes your way.

We can’t offer a ‘better’ solution here because both have pros and cons.

Our trip was mainly booked in advance which meant we spent less but we had to put up with a lot of disappointing rain days, as you will see in the photos below!

Need a hand planning your New England fall road trip? Our popular 40+ page New England Fall Road Trip Guidebook includes the 10 best places to visit, 8 example itineraries ranging from 5-14 days and an extensive interactive map to help you plan a successful leaf-peeping vacation.

Top Tips For Planning Your New England Fall Road Trip Itinerary

Finally, before we jump into the 10 unmissable stops and the New England fall road trip itineraries, let’s have a quick look at some important tips to consider when planning your vacation:

• New England is insanely popular in fall.
• Booking accommodation in advance will save you a lot of money.
• Carefully plan where you want to spend each night based around hikes and photography.
• Start in the North and work South through New England.
• Expect frequent rain and clouds in fall and accept that there’s nothing you can do about it!
• Always carry loads of water and snacks in the car.
• Try to find elevated vantage points as often as possible.
• Some of the best and most unique fall photos are along rural country roads.
• You need multiple spare batteries for your camera!
• You can use a drone in many parts of New England for aerial photography.
• Don’t worry if you miss ‘peak’ colors.

Our popular road trip resources:

• Road trip packing list essentials
• How to plan the perfect road trip

10 Places You Can’t Miss On The Best New England Fall Road Trip

Let’s take a closer look at the 10 stops we think are unmissable on a first New England trip to see the fall colors.

1. Lake Placid, New York

Lake Placid of 1980 Winter Olympics ‘Miracle on Ice’ fame is located at the heart of New York’s revered Adirondack Mountains. It is the perfect base for adventure activities throughout all four seasons, from hiking in Summer to skiing in Winter.

The charming town of Lake Placid is an incredibly popular centralized location for leaf peeping in the Adirondacks. As a result, hotels here are in high demand and not cheap from the end of September until mid October. We know from experience when our bank balance took a mighty hit!

Walk around Mirror Lake in town for the easiest way to soak up gorgeous fall colors. If you have time and enjoy challenging hikes, you can’t miss Mount Marcy. It isn’t the prettiest trail but it is the tallest peak in New York.

Things To Do In Lake Placid, NY

• Take a relaxing walk around serene Mirror Lake.
• Visit the Olympic ski jumping complex.
• Photograph John Brown barn.
• Drive to the summit of Whiteface Mountain.
• Take the Cloud Splitter cable car to Little Whiteface.
• Walk through picturesque High Falls Gorge.
• Hike Mount Marcy, the tallest peak in New York.

Where To See Fall Foliage In Lake Placid, NY

• Mirror Lake in town is gorgeous, walk through residential areas surrounded by colorful trees.
• John Brown barn is a hidden gem for fall colors.
• The top of the ski jump provides sweeping views over the Adirondacks.
• Mount Marcy summit is the highest point in the entire region, providing the best views over rolling hills.
• Whiteface Mountain and Little Whiteface offer more stunning views of fall foliage.

Read our Lake Placid guides for more information:

• 10 best things to do in Lake Placid NY
• Mount Marcy complete hiking walkthrough
• 8 best hotels in Lake Placid NY

2. Burlington, Vermont

Burlington in Vermont might not be the first place you think of for a New England fall foliage road trip destination. However, it is one of the easiest places outside of Boston to fly into the region if you are visiting from further afield.

The small town also happens to be filled with beautiful and radiant foliage colors at every turn. From lakeside bike paths to park towers with stunning views, Burlington is the perfect stop off between Lake Placid and the more famous foliage destination of Stowe.

Hotels in downtown Burlington can be limited and expensive in Autumn, so if you are visiting New England on a budget, try looking for hotels in surrounding villages and towns.

Things To Do In Burlington, VT

• Eat, drink and soak up the atmosphere along Church Street.
• Walk through Waterfront Park alongside Lake Champlain.
• Cycle the Burlington bike path to Grand Isle.
• Explore Ethan Allen Homestead and Museum.
• Stand on top of Ethan Allen Tower for amazing views.
• Taste chocolate at Lake Champlain Chocolates flagship store.

Where To See Fall Foliage In Burlington, VT

• Anywhere along the Lake Champlain waterfront where there are trees.
• Ethan Allen Park and the top of the tower in particular have the best fall foliage views in Burlington.
• Ethan Allen homestead and museum are surrounded by beautifully colorful trees.

Read more about Burlington:

• 10 best things to do in Burlington VT
• 8 best hotels in Burlington VT

3. Stowe, Vermont

Stowe is one of the unmissable fall foliage classics on any New England road trip. The white church in town is one of the most photographed churches in the US and almost all of those photographs are taken in fall.

The town is quaint and attractive but be sure to spend the majority of your time up in Stowe Mountain Resort. This is where you will find hikes, Mt Mansfeld, waterfalls and Smugglers Notch.

Colors will change first up in the higher elevations. So, if you’re a little early, head up to the resort. On the other hand, if you’re a little late, stick to the lower elevations around Stowe town for the most vibrant colors.

Personally, we love to hike, we like flying our drone and we enjoy photographing waterfalls. Stowe was one of the best stops on our New England fall road trip circuit for allowing us to do all of those things.

Things To Do In Stowe, VT

• Photograph the famous white church in Stowe town.
• Drive or hike to the summit of Mount Mansfield.
• Drive through stunning Smugglers Notch pass.
• Ride a bike along Stowe Rec Path or Lamoille Valley.
• Take the SkyRide Gondola to Mt Mansfield.
• Hike a wide range of awesome trails.
• Visit both Bingham Falls and Moss Glen Falls.

Where To See Fall Foliage In Stowe, VT

• In Stowe town, the iconic white church backed by a hill of fall colors is unmissable on your New England road trip.
• But the best colors are in Stowe Mountain Resort. The drive up from town is gorgeous.
• No matter how you get to the top of Mt Mansfield, you can guarantee spectacular fall foliage views.
• Smugglers Notch is our top recommendation for Stowe. If you have a drone, this is the place to fly.

Read more about Stowe, Vermont:

• 15 best things to do in Stowe VT
• 12 best hotels in Stowe VT

4. Woodstock, Vermont

Woodstock in central Vermont is arguably the most picturesque and charming town you will visit on your New England fall road trip itinerary. It truly is like something out of a fairytale. We had no choice but to include Woodstock in our popular guide to the 50 best places to visit in the USA .

Remarkably pretty farms with golden leaves dancing in sunlight and reddish-brown leaves covering the ground create picture perfect scenes. Sleepy Hollow Farm and Jenne Road Farm are featured on many fall foliage calendars you will see in shops on your visit to New England.

Don’t miss the many stunning historic covered bridges around Woodstock. Middle covered bridge is right in town, Taftsville and Quechee are very close by and Cornish-Windsor is a 30 minute drive. The beautiful bridge in the photo below is a privately owned bridge near South Woodstock on the main road to Jenne Farm.

Woodstock is one of the more expensive places to visit on a road trip through Vermont, but it is worth taking a hit on the extra chunk of budget. Simply driving around the narrow country roads near Woodstock for a few hours would provide enough fall foliage colors to last a week of photography.

Things To Do In Woodstock, VT

• Walk around the charming town and admire diverse architectural styles.
• Photograph two postcard perfect farms – Jenne Road Farm and Sleep Hollow Farm.
• Visit a host of historic and stunning covered bridges.
• Explore Marsh Billings Rockefeller Park and hike to amazing viewpoint overlooking Woodstock.
• Visit nearby Quechee Gorge and village.
• See Jersey dairy cows at Billings Farm and Museum.

Where To See Fall Foliage In Woodstock, VT

• Woodstock is incredibly photogenic during fall throughout the town and immediate surroundings.
• The lookout over Woodstock from Mount Tom hike is iconic fall photography.
• The best two fall photographs in Woodstock are at Jenne Road Farm and Sleepy Hollow Farm. They are two truly unmissable stops on your New England fall road trip itinerary.
• Drive your car around the narrow rural roads near Woodstock for some of the most special colors.

Read more about Woodstock, Vermont:

• 15 best things to do in Woodstock VT
• 7 best hotels in Woodstock VT

5. Manchester, Vermont

Similarly to Stowe, Manchester is a four season resort with skiing in Winter and hikes during Spring or Summer. In fall, the town located in the heart of Green Mountain National Forest transitions into a colorful paradise for leaf-peepers.

Manchester can be split into the old historic district and the newer modern resort town. The newer part is livelier and closer to amenities but the historic district is quieter, prettier and more colorful.

Use Manchester as a base for one night to explore nearby elevated areas for some of the most expansive views of rolling hills on a New England fall road trip.

Equinox Mountain is the tallest peak in the area. You can hike it or drive it to open up far-reaching views over three US states. But our top tip is to simply stick to the narrow country roads again and you will find more unique fall foliage photographs.

Things To Do In Manchester, VT

• Drive the Skyline Auto Toll Road to Mount Equinox summit.
• Explore Hildene, the Lincoln Family Home.
• Walk around quaint Manchester Historic Village District.
• See the American Museum of Fly Fishing Museum exhibits.
• Buy a book in popular Northshire bookstore.
• Visit nearby covered bridges.
• See the Bennington Battle Monument.
• Visit Robert Frost stone house museum.

Where To See Fall Foliage In Manchester, VT

• Manchester is the heart of the Green Mountains, so the entire area surrounding the town is staggeringly attractive.
• Rolling hills for endless miles covered in glowing fall colors can be seen from any elevated vantage point.
• Equinox Mountain summit provides the best panoramic views over three states.
• Another place you jump in the car and find unique fall photography opportunities on rural roads.
• Manchester Historic Village District is leafy and the church is surrounded by golden yellow leaves.

Read more about Manchester, Vermont:

• 15 best things to do in Manchester VT
• 9 best hotels in Manchester VT

6. Franconia Notch State Park, New Hampshire

Franconia Notch is one of New Hampshire’s premier tourist regions for hiking, picturesque mountains, skiing and of course fall foliage. A two lane highway mountain pass dissects the Kinsman and Franconia mountain ranges, with a number of fantastic recreational stops along the way.

Artists Bluff is a very short but steep hike leading to a rocky ledge. Its summit overlooks Echo Lake and is most popular in fall when the colors change. As you can see, we hiked the trail on an incredibly cloudy and grey day, which doesn’t help with highlighting the beauty of this viewpoint. We have included Artists Bluff in our popular guide to the 50 best hikes in the US .

Franconia Notch State Park is where you will find the stunning Flume Gorge hike. A little over 2 miles of waterfalls, narrow gorges and forested paths welcome thousands of visitors each year. For us, the best part of Flume Gorge were the two ultra-photogenic covered bridges; Flume and Sentinel Pine.

Things To Do In Franconia Notch State Park, New Hampshire

• Hike the short but steep trail to Artists Bluff summit for stunning views.
• Walk through impressive and extremely popular Flume Gorge.
• Hike Cannon Mountain or take the Cannon Mountain Aerial Tramway.
• See a whole host of waterfalls or hike one of a dozen other mountain trails.
• Ski Cannon Mountain Resort in Winter.

Where To See Fall Foliage In Franconia Notch State Park, New Hampshire

• The single most well known fall foliage photograph in Franconia Notch NH is from the summit of Artists Bluff.
• However, don’t miss the chance to walk through the incredibly picturesque Flume Gorge in fall.
• Not only are the colors vibrant, but waterfalls are attractive and two special covered bridges are incredibly photogenic.
• Anywhere at elevation, which means every hike up a mountain side or the tramway with sweeping valley views.

Read more in our Franconia Notch guides:

• Artists Bluff Trail Fall Foliage Hike
• Flume Gorge Complete Hiking Walkthrough

7. Kancamagus Highway, New Hampshire

New Hampshire’s supremely scenic Kancamagus Highway is one of the very best parts of New England to road trip in fall foliage season. We would put it firmly in the category of ‘unmissable’.

The road between Lincoln and Conway NH is only 35 miles long, but it 35 miles of pure foliage bliss. You can either drive it in one go and simply soak up the colors roadside. Or you can stop at a multitude of overlooks, hiking trails, waterfalls, lakes and covered bridges.

If there’s one part of your New England road trip itinerary to time it right for peak foliage colors, you would do well to beat the Kancamagus Highway in its prime.

A note for photographers and videographers – You can use your drone in many parts of the Kancamagus Highway. We captured amazing photographs and videos of endless miles over rolling hills covered in radiant color.

Things To Do On Kancamagus Highway, New Hampshire

• Stop at various high elevation overlooks with spectacular views over White Mountain National Forest.
• Walk to Sabbaday Falls, Champney Falls and Lower Falls.
• Hike Lincoln Woods or Mount Chocorua.
• Walk out on Rocky Gorge boulders.
• Photograph Russell-Colbath House and the picture perfect Albany Covered Bridge.
• Explore ponds and lakes to your hearts content.

Where To See Fall Foliage On Kancamagus Highway, New Hampshire

• Views over rolling hills from every overlook are astonishing in fall.
• Once the Kancamagus Highway reaches its highest elevation, you will see an ocean of color in all directions.
• Walk through any forest trail or along any waterfall hike to immerse yourself into those foliage colors.
• Albany covered bridge is one of the most picturesque bridges you will find in New England.
• Rocky Gorge and nearby lake with reflecting fall colors are wonderful.
• Even on both ends of the road in Lincoln (Loon Mountain) and Conway the colors are vibrant.

Read more about the Kancamagus Highway:

• 13 best places to stop along the Kancamagus Highway in fall

8. Mount Washington, New Hampshire

At 6,288 ft tall, Mount Washington is the tallest peak in Northeastern United States. It is renowned for wild and unpredictable weather, including the recording of a world record wind speed over over 230 mph.

As our images indicate, Mount Washington can be very wet and cloudy in Autumn. But if you get slightly more luck on your road trip and time it on a sunny day, you will enjoy some of the most beautiful colors and scenery in the entire region.

Avid hikers can climb to the summit, otherwise you can take a historic cog rail train or drive up an auto toll road to reach the top. Views from almost 2,000 meters high over an ocean of bright colors are incredible.

Things To Do Around Mount Washington, New Hampshire

• Hike a very challenging but rewarding trail to the summit of Mount Washington.
• Consider a night hike, fall colors won’t matter in the dark but it is hugely popular for astro and sunrise photography.
• Alternatively, drive the Mt Washington Auto Road to the summit.
• Or, take the most scenic and historic route to the top – by Cog Railway.
• Conway scenic railroad nearby ventures deep into fall foliage forest.
• Endless miles of hiking, 100 waterfalls and a handful of covered bridges to discover.
• Crawford Notch State Park is close by and features more views, hikes and waterfalls.

Where To See Fall Foliage Around Mount Washington, New Hampshire

• Just gain elevation in the White Mountains and you’ll open up valley views with a sea of foliage colors.
• Mt Washington summit is the iconic NH vantage point for sweeping Autumnal vistas.
• For a unique experience, the Conway Scenic Railroad cuts through some of the best colors in NH.
• Crawford Notch State Park is stunning in fall, with fantastic valley views from hikes.

9. Lake Winnipesaukee, New Hampshire

Heading due South of Mt Washington you will find Lake Winnipesaukee encircled by gorgeous fall foliage colors. Unfortunately for us, the rain was back in full swing but you can still see how vibrant the colors are in this area.

You can drive an 81 mile loop road around the entirety of the lake, or take to the waters aboard M/S Mount Washington cruise boat.

Visit Castle in the Clouds for family entertainment and hiking, Weirs Beach for arcades or Wolfeboro for a more relaxing experience. The most popular trail in the area is Mount Major, which we highly recommend for hikers looking for excellent views over the lake.

Things To Do Around Around Lake Winnipesaukee, New Hampshire

• Take a cruise on the M/S Mount Washington.
• Or rent a boat of your own for the day.
• Ride the Lake Winnipesaukee scenic railroad.
• Try your hand at arcade games in Weirs Beach.
• Hike the popular half day trail to Mount Major summit for fantastic lake views.

Where To See Fall Foliage Around Lake Winnipesaukee, New Hampshire

• Elevation is your fall foliage friend around the lake if you want expansive views.
• Mt Major is the perfect moderate hike to include on your New England fall road trip itinerary.
• But nearby Belknap Mountain is also a popular choice for fall hikers.
• Gunstock Mountain Resort has zip lines and ski lifts for easy elevation gain.
• For easier and more close up Autumnal color vistas, simply hire a boat on the lake and explore.
• Or sit back, relax and soak up the views on Lake Winnipesaukee scenic railroad foliage tour.

10. Acadia National Park, Maine

Acadia finds itself in the list of top 10 most visited and best US National Parks each year. Millions of tourists descend on Bar Harbor annually to enjoy a diverse range of amazing things to do inside the awesome park.

Varied hikes suitable for all ages and abilities, including the famous adrenaline pumping climbs Beehive Trail and Precipice Trail , are a huge draw. But despite being a typical Summer destination in the north of America, Acadia is equally as popular in Autumn and that is purely down to its glowing fall foliage colors.

Sunrises from Cadillac Mountain or Schoodic Point can be extraordinarily beautiful if conditions are right, and sunset at Bass Harbor Head Light is a very highly regarded spectacle. You will need to bring your best hiking gear, spare camera batteries and a lot of energy to the wonderful National Park in Maine.

The only problem you will face with including Acadia on a New England fall foliage road trip is its location. You will have a long drive to and from Acadia from Vermont or New Hampshire. However, if you have the time, it is unquestionably worth the extra effort.

Things To Do In Acadia National Park, Maine

• Hike various amazing trails from easy to hard (to exhilarating!).
• Photograph stunning sunrises, landscapes and Bass Harbor Head Light.
• Drive to Cadillac Mountain summit, the tallest peak on the US east coast.
• Walk or cycle maze-like carriage roads through the park.
• Explore Jordan Pond and swim in Echo Lake.
• Eat and drink in glitzy Bar Harbor, Maine.

Where To See Fall Foliage In Acadia National Park, Maine

• Mountain summits from any hike opens up special views over rolling hills covered in fall colors.
• Carriage roads are the perfect way to explore forested trails which are surrounded by trees.
• Drive the national park loop road for easiest access to fall colors.
• Jordan Pond in particular is encircled by vibrant autumnal hues.
• Cadillac Mountain summit opens up 360 degree views over Maine and the ocean.

Read our Acadia National Park guides to learn more:

• 17 best things to do in Acadia National Park
• 10 hikes you can’t miss in Acadia National Park
• Where to stay in Bar Harbor and Acadia National Park
• 10 key things to know about visiting Acadia in the fall

Planning Your New England Fall Road Trip Itinerary

New England is an enormous region and choosing exactly where to visit can be challenging. Here are a few questions to ask yourself before you begin plotting a route:

• Which places are top of your list? Vermont? New Hampshire? Acadia?
• How many days can you spare on your trip?
• Do you want to book accommodation in advance or take it day by day?
• Are you in New England solely to see and photograph fall colors?
• Or are you focused primarily on hiking with colors as an added bonus?
• Do you want to use small and quaint towns as your main places to stay?
• Or are you more interested in being rural and remote each night?
• What is your budget? Can you afford to splurge on activities?

Once you have an idea about how you see your road trip panning out, use that idea as a guide to make the best decisions based on your travel style.

Next, we will go through a number of potential scenarios for 5 day, 7 day and 10 day road trip examples through New England in fall.

Use the examples as a reference but remember, they are generic and based on how we personally would plan our itineraries with hikes and photography in mind.

5 Day New England Fall Road Trip Itinerary

Only having 5 days isn’t as much of a negative as it might usually be. Yes, you are going to have to be selective and it is going to be none stop action. But one of the major benefits to a road trip in fall is that all of the best scenery is seen when driving.

Also, the smaller states of Vermont and New Hampshire don’t require a huge amount of drive time between their most scenic places for fall foliage. Include Lake Placid in the Adirondacks and you can easily tick off most of the places in our list in 5 days.

Another consideration is with just 5 days you don’t need to worry as much about ‘following’ peak fall colors. They won’t change too much in that time frame when compared to 10 days.

Example 1 – Lake Placid NY to Manchester VT

D1 – Lake Placid : Walk around Mirror Lake, drive up Whiteface Mountain and explore High Falls Gorge. Stay in Lake Placid.

D2 – Burlington and Stowe : Walk down Church Street, cycle Burlington bike path, explore Smugglers Notch and Stowe Mountain Resort, sunset at Stowe church. Stay in Stowe.

D3 – Franconia Notch and Kancamagus Highway : Hike artists bluff trail, walk around Flume Gorge, drive Kancamagus Highway and down to Wolfeboro. Stay in Wolfeboro on Lake Winnipesaukee.

D4 – Lake Winnipesaukee and Woodstock VT : Spend morning exploring the lake or hike Mt Major, then drive to Woodstock in Vermont via Cornish-Windsor covered bridge, Quechee Gorge and Taftsville covered bridge.

D5 – Woodstock and Manchester : Visit the farms near Woodstock, drive through Green Mountains to Manchester and end at the top of Equinox Mountain.

You could start and end in New York City if flying into Newark or JFK works from your origin and budget. Alternatively, Montreal would be a better place to start for Lake Placid, hire a car and drop it off in NYC or Boston after leaving Manchester, VT.

Example 2 – Lake Winnipesaukee NH to Manchester VT

D1 – Lake Winnipesaukee : Explore the lake, hike Mt Major, take a cruise and stay in Wolfeboro.

D2 – Kancamagus Highway and Franconia Notch : Drive Conway to Lincoln across Kancamagus Highway, hike Flume Gorge and Artists Bluff. Sleep in Franconia.

D3 – Stowe and Burlington : Stowe church, hike to waterfalls in Stowe Mountain Resort, drive Smugglers Notch and on to Burlington. Ride the bike path for sunset. Stay in Burlington.

D4 – Lake Placid : Whiteface Mountain, High Falls Gorge, Ski Jump and Mirror Lake. Or hike Mount Marcy instead but that is a full day commitment. Stay in Lake Placid.

D5 – Woodstock and Manchester : Visit the farms, covered bridges and drive through Green Mountain countryside to Manchester, finish with Equinox Mountain again.

This version would allow for a round trip loop from Boston, MA airport or Portland, ME airport.

The key to making the most of this shorter trip is to accept that you will be in the car driving a lot but that is where you will see most of the best scenery.

7 Day / One Week New England Fall Road Trip Itinerary

With a week, you can get more creative, include more places or take things slower. You have more flexibility but still not enough time to add a trip to Acadia, unless you really can’t miss it and don’t mind the driving.

Colors can change a noticeable amount in 7 days, so (if possible!) factor in starting your one week trip just before ‘peak’ begins.

Either of the 5 day examples above would work with 7 days by simply taking more time in certain spots. The alternative is to add in more places to visit. Let’s look at both:

Example 1 – Lake Winnipesaukee NH to Manchester VT

D2 – Kancamagus Highway : Take the awesome road trip slowly, stop at every attraction and stay in Loon Mountain or Lincoln.

D3 – Franconia Notch and Stowe : Hike Flume Gorge and Artists Bluff before driving to Stowe to photograph the church. Hike the waterfall trails and see Smugglers Notch. Stay in Stowe.

D4 – Burlington and Lake Placid : Church Street and Burlington bike path, then drive to Lake Placid, get stuck into the best bits of Lake Placid and spend the night there.

D5 – Lake Placid and Woodstock : Spend the morning in Lake Placid and drive to Woodstock later in the day. Hike to Mount Tom for amazing views over Woodstock. Stay in Woodstock.

D6 – Woodstock : Sunrise at Sleepy Hollow Farm, Jenne Road Farm, visit the nearby covered bridges and relax in town. Drive to Manchester later in the day to stay over.

D7 – Manchester : Hildene, Manchester old town and stunning Green Mountain country roads, finish at Equinox Mountain.

This variation could begin and end at either Boston, MA or Portland, ME as in the itinerary above. It just gives you more downtime and time to fully explore the places you will visit.

Example 2 – Manchester VT to Lake Winnipesaukee NH

D1 – Manchester : Drive from Boston airport to Manchester, spend the day at Hildene, Equinox Mountain and exploring the town. Stay in Manchester.

D2 – Woodstock : See the best of Woodstock and spend the night.

D3 – Stowe : Hit the top highlights in Stowe and stay there for the night.

D4 – Mount Washington : Take the cog train, drive to the summit or even take on the hike. Sleep in North Conway.

D5 – Kancamagus Highway : Spend a full day on The Kanc. Sleep in Loon Mountain or Lincoln.

D6 – Franconia Notch : Hike Flume Gorge and Artists Bluff but drive to Lake Winnipesaukee later to spend the night.

D7 – Lake Winnipesaukee : Spend the last day around the lake, cruising, hiking or relaxing.

This loop direction was reversed to give an idea about how you could make it work in a clockwise route. Again this would be starting and ending in Boston or Portland, with JFK or Newark as alternative options.

Instead of driving out to Lake Placid, you could stick to Vermont and New Hampshire, which is where the very best colors are found.

10 Day New England Fall Road Trip Itinerary

With a full 10 days to spend on your New England fall road trip, you can either max out your itinerary and see all of the best bits or choose to spend more time in fewer places.

Personally, we’re the max out itinerary type and we would definitely include Acadia National Park in our 10 days. It adds in some serious driving time but the journey there is picturesque, rural and most importantly colorful.

Here’s one way you can include each of the places mentioned in this list, including Acadia National Park (this is the way we drove but we spent 14 days doing this route with other non-fall foliage places included in our itinerary):

Example 1 – Lake Placid, NY to Manchester, VT via Acadia National Park, ME

D1 – Lake Placid : Spend the day hiking and surrounded by gorgeous colors. Sleep Lake Placid.

D2 – Burlington : Full day exploring town and cycle the entire bike path to Grand Isle. Stay in or near Burlington.

D3 – Stowe : Smugglers Notch, Mountain Resort, Mt Mansfield and church in town. Stay in Stowe.

D4 – Franconia and Kancamagus Highway : Hike Artists Bluff and Flume Gorge, drive The Kanc and sleep in North Conway.

D5 – Mt Washington and drive to Acadia : Drive to the summit or take the cog train before driving US-2 all the way to Acadia. Sleep in Bar Harbor.

D6 – Acadia : Sunrise Cadillac Mountain, Hike Acadia Mountain and Beech Mountain, sunset at Bass Harbor Head Lighthouse. Stay in Bar Harbor.

D7 – Acadia : Sunrise Schoodic Point, Hike Beehive Trail and Precipice Trail, Walk around Jordan Pond, Great Ocean Path and carriage roads by bike to see the best fall colors. Final night in Bar Harbor.

D8 – Lake Winnipesaukee : Final morning in Acadia, long drive to Wolfeboro and explore Lake Winnipesaukee.

D9 – Woodstock : Photograph Sleepy Hollow and Jenne Road, hike to Mt Tom, see covered bridges.

D10 – Manchester : Hildene, Mount Equinox, nearby Bennington battle monument and covered bridges.

Tips For The 10 Day Itinerary

The only concern with this itinerary is the inclusion of Acadia National Park. It’s a 4 hour drive from Mt Washington to Acadia and 4 hours 20 minutes back from Acadia to Wolfeboro.

However, if you do have more time you can include stops on the way to and from Acadia to break up the longer drives. US-1 and US-2 are picturesque but slow going. If you’re pushed for time, take the less scenic but faster I-95 instead.

Alternatively, if you’re not so bothered by Acadia, plan to spend even more time in each of the other 9 places in this list. That would give you wiggle room in case of bad weather and plenty of time to relax.

Notice how the route starts furthest north and loops around Acadia then comes back further south?

That’s because with 10 days you should try to ‘follow’ the peak colors as they transition southwards over the first two weeks of October.

New England Fall Road Trip Map

Red Markers – Locations of the 10 best places to visit on a New England fall road trip itinerary.

Click or touch the map to activate.

Zoom in and out, move around the map of New England to find locations for the best places to visit in the area.

More From New England

• Best things to do in Burlington Vermont
• Best things to do in Woodstock Vermont
• Driving the Kancamagus Highway in fall
• How to visit Flume Gorge in New Hampshire
• The best things to do in Lake Placid New York
• The best things to do in Stowe Vermont
• Top things to do in Manchester Vermont
• Unmissable things to do in Acadia National Park

We hope this New England fall foliage road trip guide with itinerary ideas helps you plan the perfect leaf-peeping vacation!

Please let us know if you have any questions about New England or need any help planning your visit in the comments below.

Happy Travels,

Mark and Kristen

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Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

29 thoughts on “New England Fall Road Trip Itinerary: 10 Stunning Stops”

I really appreciate your compressive guide to New England for travel in the Fall. We have enjoyed most of the areas you mention in years past and loved it. My sister is visiting from Australia at perfect Fall Foliage time so we’re planning to do your 10-day roadtrip this year. I was wondering if you have an App you prefer to use to plan each segment of the roadtrip. I used Roadtrippers earlier this year and found it good, but would welcome your suggestions for a roadtrip App. I plan to download your digital guide as well. Thank you and happy travels.

Hi Sharon, we’re happy to hear you will be visiting New England again and this time with your sister. If you are looking for alternatives to Roadtrippers you could check out Wanderlog which is another useful resource. But to be honest we don’t use any apps for our road trips except for the basic and free Google Maps app. We plot points for attractions, restaurants and hotels as we research before visiting a new place, and we plan ahead so we can really get organized. If you download our digital guide and go to the end, you will find a map we created that will open in your Google Maps app and it already contains the locations for top attractions, foliage photo spots, hikes, restaurants and hotels that we discuss throughout the guide. You can of course see more places but we have preloaded the map with the essential spots to visit around New England in fall. Have a fantastic trip!

@Mark and Kristen Morgan, Thank you so very much for your advice. I downloaded the digital guide to use. So looking forward to this trip and having your guide to get organized makes this a lot less daunting. Keep up the great work and happy traveling.

Hi Sharon, Visiting New England in fall is an amazing trip and you will have a wonderful time! Thanks so much for taking the time to leave a nice comment and downloading our guide. Just let us know if you have any specific questions as we get closer to fall season 🙂

@Mark and Kristen Morgan, I have accommodations booked from Lake Placid to Woodstock. Since we want to add a couple of nights in Boston to walk the Freedom Trail and visit the Boston Tea Party site, would you recommend skipping Manchester, Vermont and going directly to Boston from Woodstock. Or, would we be missing out if we skip Manchester. Appreciate your advice.

Hi Sharon, you will have covered almost all of the best fall spots between Lake Placid and Woodstock. We like Manchester but it isn’t going to ruin your trip if you skip it, especially if you really want to see more of Boston. After 10 days or so you will have had your fill of fall colors anyway, so Boston will be a welcome change of scenery and pace. Have a fantastic time!

I would love a copy of the book as well, to use as we travel Thank you for a wealth of information!

Wow, amazing information, thank you. Have you written it in book form by any chance? I would love to drive with the book on hand for reference.

Hi Helen, you have asked at just the right time. We are currently in the process of creating a digital guidebook filled with key information and itinerary ideas for the New England fall road trip. It will be ready within the next week or so and we will email you once it is live. You will be able to either keep it on your smartphone or print it if you prefer to have a paper copy.

@Mark and Kristen Morgan, I’m using this article to plan our New England fall leaves trip and would also be interested in a copy of your digital guidebook, please. The information you provide is outstanding — thank you! ~ Carol

Thank you, Carol! We’re happy to hear you are planning a New England trip this fall. You can follow this link to see more details about our digital guidebook. If you do purchase the guidebook, remember to open up the map on page 45 when you are in each place to see the best hikes, foliage spots, attractions, restaurants and hotels. And if you have any specific questions, feel free to ask away. Have a fantastic trip!

Hello! What a wonderful site you have given us :). Question…do any of the New England fall road trips include the Berkshires? I would love to include a quick visit to The Mount/Edith Wharton’s home. Thanks, Jo

Thank you, Jo! Yes absolutely, you could easily add The Mount / Edith Wharton’s Home to the end of our 10 day New England fall road trip itinerary because it is just 1 hour 30 minutes drive to the south of Manchester VT (which is the last stop in our guide), before heading back to the Boston / NY airports. It wouldn’t be much of a detour and if you are heading that way you might also want to consider including a short drive along scenic highway 2, also known as The Mohawk Trail. Have a fantastic trip later this year!

Hi There! We are flying into Portland, (Sept 23rd) Maine and flying out of Boston, Mass (October 2nd) We have about one full week for our Fall Foliage road trip. Knowing we arrive Portland and depart Boston, what would you map out for itinerary.

Part II question, I prefer staying at one hotel for a few days and taking day trips as opposed to staying one night in several places.

Would it be wise to stay 3 nights near Acadia Nat’l Park and then 3 nights in New Hampshire (near all of the Franconia State Park and Kancamagus Hwy ?

Hi Erin, yes staying 3 nights in Bar Harbor and then 3 nights somewhere near Franconia Notch sounds like the best idea if you would prefer to stay in one hotel for each part of your trip. You can easily visit the most popular fall foliage areas in VT and NH from Franconia. Depending on how much driving you want to do, you could split your days into Vermont and New Hampshire. So one day you do Stowe, Woodstock and Manchester (the driving in between is just as picturesque as the towns), then another day you do Mt Washington, Kancamagus, Artists Bluff and Flume Gorge (which are all much closer together). Then stop at Lake Winnipesaukee on the way down to Boston. Hopefully the peak colors will be in north / central VT and NH early Oct for your trip – have a great time!

Love your site! we are planning a a Fall Foliage trip for 2023 over our 34th Anniversary. thinking any where from 10 – 14 days from the last week in Sept. to the first week of Oct. We are thinking to end our trip in Boston for a few days. If I followed tour 10 day trip guide would it make sense to fly into Albany, NY and out of Boston. Or are we better off to make Boston a long weekend trip?

Hi Randy, thanks for getting in touch and we’re happy to hear you’re planning a trip to New England next year, congrats on the 34th! Absolutely, flying into Albany and out of Boston makes perfect sense. If you make your trip 14 days total, you can follow the 10 day itinerary in our guide and then spend 2 or 3 days in Boston at the end. Something to consider is whether or not you want to see Acadia NP, it is a stunning place but it’s a long way out from the rest of New England’s top foliage spots. If you don’t include Acadia, you can spend longer in the fall color hotspots of Stowe, Woodstock and Manchester in VT, plus Franconia Notch, Kancamagus Highway and Lake Winnipesaukee in NH. Let us know if you have any more questions and best of luck with planning!

We are planning a trip to Maine in the fall of 2023 for our 40th anniversary for a total of 7 days. We would be interested in mainly leaf peeping,Arcadia NP, sight seeing/boat tours, driving the back roads and easy hikes. I really like the coast. Now that I have run across this post, I am rethinking our trip. What city should we fly into? Do you recommend spending 2 days in Arcadia NP? Should we hit some of the areas you mentioned in NH? I don’t think we have time to do your whole itinerary in 7 days. Your thoughts?

Hi Randi, glad to hear you have a trip planned to Maine for your 40th anniversary – congrats! Honestly, 7 days isn’t enough time to be rushing around New England trying to cram in everything. If you like the coast and you want to do Acadia, why not fly into Portland in Maine and slowly drive up to Bar Harbor via the back roads? Acadia is great but it is touristy and expensive, plus you won’t get the best fall colors (when compared to NH or VT). Boothbay Harbor is a nice place to stop between Portland and Bar Harbor, and you can do whale watching tours right out of the small town. If Portland doesn’t work for flight times or prices, Boston will be your best bet. Let us know if you need any more help before you travel next year.

Hi. I’m glad I found this. We are planning our 50th Anniversary to see Vermont and Maine in late September. Is it possible to stay in one place and drive to see the sights? We don’t want to keep changing hotels. This is a lifetime dream for us. Thank you.

Hi Jan, congrats on your 50th anniversary! Without knowing exactly which places in Vermont and Maine you want to see, it is possible to stay in one place but that would mean quite a lot of time spent in the car. If you have a 50/50 split, maybe stay somewhere in New Hampshire in the middle? Or if you plan to spend more time in VT, stay somewhere just inside VT near the NH border? Somewhere near Franconia NH might be a good fit so you are central to most of the fall hot spots and far enough North to see peak colors at the end of September. Have a great time!

Great article! While planning and researching for our New England Fall Foliage Adventure we saw right away that trying to predict “peak” conditions was a difficult proposition, at best. With that in mind and because we have a bit of time on our hands we decided our adventure would be from mid September to mid October 2022. We have booked all of our accommodations and now it’s all about deeply researching the areas and filling in the days. Finding your well written and in depth blog helped confirm our research was spot on and added to our happiness that we are actually going to pull this off. Plus, now we have an excellent study guide to boot! Bring on the trails, the mountains, the breweries, the lobster, cheese, cider donuts, Octoberfests and even the rain! Thank YOU and keep up the fantastic and insightful work!

Hi Jeff, thanks for getting in touch and we are so happy to hear you have planned a full month up in New England! Your list of activities is spot on – hiking, scenery, fall colors, food and beer … recipe for a perfect trip! Good luck filling in the days and hopefully you’ll get optimal weather conditions leading into the peak, just remember to keep an eye on the peak fall colors tracker when you are on site in New England. Have a wonderful trip!

Hello! This post is really very useful! We are planning to go to New England from September 30th to October 8th (we have already booked our flight from Italy). Since we would like to spend a couple of days in Boston too, do you recommend to begin with Boston and then start our road trip or to do the other way round? We would very glad if you could give us more details! Thanks a lot!

Hi Simonetta, thanks for getting in touch and we’re happy to hear you will be visiting New England this fall! This is a tough question because nobody can predict when “peak” fall colors will be in each part of New England. You can keep an eye on a live peak foliage tracker and book everything last minute, but that is risky as accommodation will book up. So, we would suggest starting with Boston and then driving up as far North as you will go on your trip (ie Stowe in VT or Franconia in NH) and then working down South to follow the peak. Please let us know if you have any more questions and you might even see us up there somewhere this year! Have a great time 🙂

I’m so happy to have found your blog post. I know how much time and effort goes into planning these type of trips, so I appreciate you writing about it and sharing it. We are looking at doing a mix of rural/city for both NH, VT, and ME. Looking closer to a 10 day trip and flexible on the dates. Would you say the hikes are fairly easy, medium, or difficult? Do you think looking into Air BNB’s out there would be better vs. hotels?

Hi Ani, thanks for getting in touch and we’re glad to hear you have a trip planned for VT, NH and ME. There are countless hikes spanning the difficulty range on this road trip route, so you do have a lot of flexibility over how long you want to spend hiking and how hard the trails are. Artists Bluff is short but has a steep climb, so we would say it is moderate but well worth it. Flume Gorge is easy and shouldn’t be missed. Acadia (if you make it that far) has a host of easy through hard hikes. Lake Winnipesaukee has plenty of hikes to suit all. If you’re looking for hard hikes take on Mt Washington or Mt Mansfield, tallest in NH and VT. You’ll likely only be spending one night or a maximum of 2 at any given place so we would say go for hotels. AirBnB’s are great for uniqueness and meeting people but for one night they are always more expensive with cleaning fees / service fees etc. By all means check prices and see if you can find any good deals or special places but we will be sticking to hotels ourselves the next time we are in New England. Let us know if you need any more help and have a fantastic trip!

Great information, love your post! We have never been to New England and would like to go see the fall colors in late Sept. or Oct. We also want to spend some time in Boston and Cape area. We are flexible on dates and number of days in itinerary. We would be interested in some hikes. After looking at you post I’m thinking Vermont and New Hampshire might work after seeing Boston. Can you help with an itinerary? We would be flying from San Diego, CA. Would appreciate any information! Thank You!

Thanks for getting in touch, Marilen – we’ll respond through email so we can provide more information.

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We are two 70 something, Southern, retired ladies planning a trip to the eastern seaboard. We would like to visit Maine, New Hampshire, Vermont, MA and Rhode Island. We will fly and then drive . Would it be better to fly further North and drive South or visa virsa? We like to see the ocean but are not beach goers, per se. We do enjoy historical sights. Our time is flexible so what time of the year would you suggest for our trip? We plan on a maximum of two weeks for our travels. Thanks so much for any advice you can give us. We have never been to this area before.

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We are volunteers. We are not travel/ booking agents. You need to have some level of research don’t knowing sone idea of where you are going.

If you are not a U.S. citizen you need to book cars with full insurance through your countries travel agrnts/ brokers thst include insurance in price.

A general route loop dtructure could look like this

Day 1 fly into Boston

Day 2-3 to maine to Acadia NP

Day 4-5 Acadia NP

Day 6 drive a route in crntral mail to New Hampshire

Day 7-9 New Hampshire and Vermont

Day 10 Massachusetts returning to Boston

Day 11-13 Boston

Day 14 fly home

This route coukd be reversed. Where you still end the trip multiple days in bodton. You could fly into nyc airport and do something like this

Day 1 fly to nyc

Day 2-3 nyc

Day 4 to VT

Day 5-7 to Acadia, np

Day 8-9 Acadia np

Day 10-11 to Boston along coast

Day 12-13 boston

In your routes you could go to montreal/ qubec city as part of the route ( might have to add a few more days)

New England is generally a late May- October season wherr leave sre on trees snd thrn colors turn in late sept- late oct deprnfing on elevation and distance from the coast. Boston peaks end October. High mountain elevations/ far north maine/ along cansfian border peak late Sept

There are other places you can go into Canada likr New Brunswick or other Maritimes provinrnces in Canada with some ferry routes in summer.

What time of year is this planned for? If you are looking into Fall colors, starting north and ending south usually works best.

There is a New England forum here that probably has itineraries that’s would help you. New England is a better description of your plan than Upper Eastern Seaboard, which would generally make it to New Jersey or Delaware.

Below is a link to TA's New England forum.  Scroll down to read some threads on what other people have done/plan to do and post there for more detailed help.  It would help to know your home airport for advice on where to fly into, how often you're okay to change lodgings and how many hours you wish to drive on any day. I think you're best to stick to just the areas you mentioned.  Plenty to see in New England.

https://www.tripadvisor.com/ShowForum-g4672736-i29525-New_England.html

Leaf peeping season is popular and therefore accommodations are expensive, especially on weekends. And the nice inns and B&Bs get booked up far in advance.

You will not be able to see everything; in fact with 2 weeks, you will just get a small taste of what's on offer. Unless you are really dying to see the Newport "cottages", I'd drop RI and concentrate on Boston and points north.

What are you interested in seeing? Art and architecture? Historical sites? Hiking and national/state parks with mountains and waterfalls? Rocky coast and lighthouses?

Here is an itinerary to consider/use as a start point:

Fly into Boston; spend a couple of days there

Newport RI (mansions, cliff walk). If foodies, you could include Providence

Northampton/Historic Deerfield/Shelburne Falls MA

Take MA-112 into VT to VT-100; head up to Waterbury VT then take US-2 then 302 in New Hampshire (White Mountains); Jackson is a nice town to overnight

Pick up US-2 again and head to Acadia National Park in Maine

Take US-1 along the Maine coast as far as Portland then back to Boston; stop at the lighthouses in Rockland and near Portland. If interested in LL Bean, go a little further south down to Freeport.

+1 for Historic Deerfield. And if you can, stay at the Deerfield Inn. The Bridge of Flowers in Shelburne Falls is one of the most delightful gardens I've ever visited.

Portland, ME has some excellent restaurants and, as you'd expect, great seafood. My recollection, refreshed by a glance at Google Maps, is that Freeport, ME and L.L. Bean are about a 1/2 hour north of Portland.

One observation about the White Mountains in NH: the roads get foggy at night. Consider this if staying at a rural location that does not have dining facilities. This is also true of the Berkshire Mts. in western MA. if you happen to get there.

On the route I suggested I forgot to mention that Warren/Waitsfield (south of Waterbury on VT-100) is where I would suggest for an overnight along the VT-100 route.

Thank you so much. We are actually thinking of flying in to one airport and flying home from our final destination. This would allow us to see more states.

Thank you. Probably fall.

Thank you. We'll be flying out of New Orleans.

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Portland (Maine) to Boston drive

Portland (maine) to boston road trip planner.

Here's a sample itinerary for a drive from Portland (Maine) to Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops . Camping along the way? Search for RV campgrounds . Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

10:00 am  start in Portland (Maine) drive for about 35 minutes

10:35 am   Kennebunkport (Maine) stay for about 1 hour and leave at 11:35 am drive for about 39 minutes

12:14 pm   Portsmouth (New Hampshire) stay for about 1 hour and leave at 1:14 pm drive for about 38 minutes

1:53 pm   Groveland (Massachusetts) stay for about 1 hour and leave at 2:53 pm drive for about 39 minutes

3:32 pm   Salem (Massachusetts) stay for about 1 hour and leave at 4:32 pm drive for about 40 minutes

5:11 pm  arrive in Boston eat at Mike's Pastry stay at The Westin Copley Place

driving ≈ 3 hours

Portland (Maine) to Boston questions

Where should I stop along the way?

Kennebunkport (Maine)   (24 answers)     Wells Beach   (3 mentions)     York Beach   (2 mentions)     restaurants around Kennebunkport (Maine):         All Day Breakfast     questions about Kennebunkport (Maine):         family vacation Portsmouth (New Hampshire)   (21 answers) Groveland (Massachusetts)   (2 answers) Salem (Massachusetts)   (26 answers)     Salem Witch Museum   (2 mentions)     The House of the Seven Gables   (2 mentions)     hotels around Salem (Massachusetts):         Hawthorne Hotel     questions about Salem (Massachusetts):         What is your favorite restaurant in Salem (Massachusetts)?         witch         What is a good nighttime tour

Where's the best place to stay in Boston?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Boston .

You can also see most people recommend as the best amount of time to visit. Find out how many days in Boston to stay.

If you're looking for a quick answer, you can check out The Westin Copley Place , which was mentioned 4 times on Trippy.

Here are some more hotels people talk about:

Want to research more popular hotels in Boston? Click the blue button below.

Where's the best place to eat in Boston?

Need some recommendations on somewhere to get food?

Trippy members suggest Mike's Pastry , which was mentioned 15 times.

Here are some more restaurants people talk about:

Want to research more popular restaurants in Boston? Click the blue button below.

What are some things to do in Boston?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Boston. Click on any question to see answers from the community!

Click the button below to explore more questions and answers related to Boston.

Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Boston to Portland (Maine) drive , or go to the main page to plan a new road trip .

Looking for ideas for more destinations within driving distance of Portland (Maine)? Try searching for places within 2 hours of Portland (Maine) .

You can also compare the travel time if you're flying or driving by calculating the distance from Portland (Maine) to Boston . Or get a full Portland (Maine) to Boston flight plan .

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

And if you know Portland (Maine) well, please help your fellow travelers and answer their questions about Portland (Maine)!

More info on this route:

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Planning a New York to Maine Road Trip Itinerary

W hether you are going for the beaches and the lobster rolls, or trying to hit peak fall foliage and everything pumpkin and apples, May through October is the perfect time to plan a New York to Maine road trip.

While it is tempting to rush through Southern New England on your way from New York to Maine, take some time to stop and see the sights along the way. This New York to Maine road trip itinerary was designed for a one-week trip, but can easily be extended to include more time at each destination or you can continue up the Maine Coast to see more of Vacationland.

This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston itinerary for additional ideas.

Or, if you want to see more of Maine, you can continue north for a road trip through the Maine Highlands . This itinerary will take you from New York City to Maine, with stops in:

• Mystic, Connecticut
• Newport, Rhode Island
• Boston, Massachusetts
• Portland, Maine

New York to Maine Road Trip

If you are taking a New York to Maine road trip, the quickest route will be under six hours through Hartford, Connecticut. This makes the best return trip from Maine, but on your way, I’d recommend taking a slightly longer and a smidge more of a scenic route on your way to Maine.

From New York City, take Interstate 95 approximately 3.5 hours (traffic can vary) to the historic seaport town of Mystic, Connecticut. If you need a pitstop along the way, downtown Stamford and New Haven both offer great dining options, or grab some lobster rolls at Ford’s Lobster in Noank, Connecticut.

Stop #1: Mystic, Connecticut

Your first overnight stop should be in the charming seaside town of Mystic. I’m not sure if it is more famous for Mystic Pizza, the 1988 film starring Julia Roberts, or the historic Mystic Seaport, a must-see family attraction. You will probably want to stay here for two nights, as there is plenty to do in town and nearby.

Mystic Seaport is a recreated 19th Century seafaring village, complete with ships, shops, and workplaces staffed with costumed interpreters ready to tell you about their craft and day-to-day life in a 19th Century town. The cooperage, print shop, and general store are all popular stops with kids. Visitors can also step on board the Charles W. Morgan, the last wooden whaling ship in the world, or get out on the water on a Mystic River boat ride.

Downtown you can grab an ice cream and watch the drawbridge go up and down as ships pass by, browse the shops, or get something to eat at one of the many seafood restaurants. In addition to Mystic Pizza, I’m a huge fan of the Engine Room for lunch or dinner, or Kitchen Little for breakfast.

Kids will also love watching the beluga whales at the Mystic Aquarium or exploring the trails at the Denison Pequotsepos Nature Center. If you are visiting in the fall, it is worth waiting in line at B.F. Clyde’s Cider Mill for some hot, fresh apple cider donuts.

If you have time to spend a couple of days, nearby you can enjoy a ride on the Essex Steam Train, a visit to the Pequot Museum on the land of the Mashantucket Pequot Nation, a lighthouse tour from New London, a day at the beach in Misquamicut State Beach in Westerly, Rhode Island, or some wine tasting at Jonathan Edwards Winery near Stonington, CT.

Read more: things to do in Mystic with kids

Where to stay: Hyatt Place Mystic (includes free breakfast) and Mystic Marriott Hotel & Spa (not in downtown Mystic but a good full-service hotel option).

Stop #2: Newport, Rhode Island

From Mystic, it is about one hour drive to your next stop in Newport, Rhode Island. You can potentially just visit for the day and continue on to Providence or Boston, but staying overnight will give you more time on the Classic Coast.

Whether you are visiting in the spring, summer, fall, or winter , there is always something to do in the historic town of Newport, Rhode Island . Once a summer getaway for the wealthy New York industrialists, Newport still attracts the yachting crowd as the “sailing capital” and the classic coast. You can do Newport in a day, as it is only an hour from Mystic, but if you want to enjoy nearby beaches, farms, or take a day trip to Providence, Rhode Island , plan on staying one to two nights.

Two must-do things when you are in Newport are paying a visit to at least one of the famous Newport Mansions and getting out on the water for a sailing tour. The Newport Mansions are former homes of the business titans like the Vanderbilts, which were once used as “summer cottages” but more closely resemble palaces than a beach house. The largest and most famous is The Breakers, but I also enjoy visiting Marble House.

If you don’t want to tour the homes, take a drive down Bellevue Avenue to see them from the front and then walk along the three-mile Cliff Walk to get a glimpse of some of the backyards, along with gorgeous ocean views.

There are many sailing options in Newport, from sunset schooner sails to seal-watching eco-tours (in the winter). Leave time to enjoy shopping and strolling along Thames Street and Broadway in downtown Newport. You can also pop into the International Tennis Hall of Fame or one of two car museums around town. There are plenty of options for a great meal, including Bowen’s Wharf, the Black Pearl, Diego’s, and Midtown Oyster Bar.

In the evening, be sure to take a drive along Ocean Drive and try to catch a sunset from either Brenton Point, the Lawn at Castle Hill Inn, or Newport Island Harbor Resort on Goat Island. On your second day, either hit the beach (my favorites in Newport are Gooseberry Beach and Second Beach) or take a drive over to the neighboring island of Jamestown to visit my favorite spot in Rhode Island, Beavertail State Park. If you prefer an urban outing (or if you are visiting on a Waterfire night), head up to Providence for the day or afternoon/evening.

Where to stay: Newport Marriott has a great location and nautical decor, The Brenton Hotel is a hip hotel in central waterfront location, and The Vanderbilt is an upscale, historic property with a great rooftop bar.

Stop #3: Boston, Massachusetts

When it is time to bid adieu to Rhode Island, drive two hours north to Boston. Now if you have extra time, you will want to spend three days in Boston, especially if you want to take some day trips to Gloucester , Rockport, or Salem, or stop at Plymouth along the way.

Boston is rich in history and charm, and like any large city, it has its fair share of great museums too. If you are interested in history, taking a walk along the Freedom Trail is a must-do. Of course, you may get more out of it if you sign up for a tour with a costumed guide.

To better understand Boston’s pivotal role in the Revolutionary War and founding of the country, pay a visit to the Boston Tea Party Ships & Museum . Kids will especially love tossing the tea into the Boston Harbor or a snack at the tea shop.

Within a short walk of the Boston Tea Party Museum, you can also visit either the Boston Children’s Museum or the New England Aquarium. If you are visiting in the summer, I’d recommend booking a whale-watching cruise in advance for an afternoon on the water and a glimpse of some magnificent creatures. If you don’t have time for a whale watch, you can still enjoy some time on the water with a harbor cruise or a ferry around the Boston Harbor Islands.

Afterward, take a walk along the Rose Kennedy Greenway and either enjoy some of the food trucks congregated there, or walk over to the North End, Boston’s “Little Italy” and pick up some cannoli at Mike’s Pastry. And while it is touristy, the street performers around Fanueil Hall are always entertaining and there are plenty of places to grab a quick bite. For a more upscale food hall, drop into the Boston Public Market or head across town to Eataly Boston.

Sports fans should try to book a tour of the “Green Monster” and Fenway Park or try to catch a Boston Red Sox game in this classic stadium. If you appreciate art, visit the Museum of Fine Arts, or the intriguing Isabella Stewart Gardner Museum nearby (and learn about the famous heist that took place there.)

While you are in town, take a stroll through the Boston Common and Public Gardens, and take a ride on a Swan Boat before you visit the famous “Make Way for Ducklings” sculpture. You can also pop into Cheers on Beacon Hill and see if anyone knows your name. Movie and television fans would also enjoy a tour with On Location Tours of popular Boston filming sites from Good Will Hunting, Ted, The Departed, and others.

Read more: Things to do in Boston with teens

Where to stay : Boston is notoriously pricey, so for a family, you may want to consider one of the following options: Residence Inn Boston Downtown/Seaport Hotel has a convenient location to downtown, North End and harbor; Element Seaport is in newer seaport district with family size rooms; and Hyatt Place Boston/Seaport District has free breakfast and a good location in popular Seaport District.

Stop #4: Kennebunkport, Maine

On your way to Portland, head two hours north of Boston to the charming coastal town of Kennebunkport, Maine. As soon as you pass into Maine, get off the highway and hightail it to Bob’s Clam Hut for some of the best lobster rolls and fried clams in New England. Then meander up the coast, taking your time to stop into a few of the best towns in the Maine Beaches region.

If you need to stretch your legs, stop in York for a walk along the 1.5 mile Cliff Walk or stock up your kitchen pantry at the Stonewall Kitchen company store. Another must-stop destination on your road trip to Maine has to be in Cape Neddick at the Nubble Lighthouse. Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door or Dunne’s Ice Cream down the street.

Just a little further along you will arrive in Kennebunkport (you might want to drive past the Bush Family compound along the way.) In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack.

We also like to head out of town to Cape Porpoise Chowder House, which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. You can stay in Kennebunkport or drive another 40 minutes to Portland, Maine. Your final destination on this New York to Maine road trip.

Where to stay: The Boathouse is a waterfront hotel right in Dock Square is perfect for when you want to be in the center of the action. If you prefer a bed and breakfast, try the The Inn at English Meadows .

Stop #5: Portland, Maine

Portland , Maine is one of the best small cities on the East Coast . Plan to spend at least a couple of days exploring Portland and the surrounding area. The park and area around Portland Head Light in Cape Elizabeth is a perfect spot for a picnic and to clamber over the rocks and watch the boats go by. When you are there, be sure to pick up a lobster roll from the Bite into Maine food truck.

Back in Old Port, take an afternoon to explore the boutiques along the harbor and wharves. There are so many amazing restaurants in Portland to try including Luke’s Lobster, Duckfat, Eventide, and Fore Street. There are also many craft breweries in the Portland area and you can board the Brew Bus for a tour if you don’t want to risk driving.

On your second day, you can take a ferry around the Harbor Islands or try a lobster cruise where you learn all about lobster fishing and even get to keep and cook what you catch. Or, spend a day shopping up in Freeport, home of the flagship L.L. Bean store.

Read more: Things to do in Portland in winter

Where to stay: Press Hotel or the AC Hotel Portland

While this New York to Maine road trip itinerary only takes you into Southern Maine, it is easy to extend this to head up to the coast with a stop at either Boothbay Harbor or Rockland before reaching Bar Harbor and Acadia National Park .

This road trip gives you a great introduction to Southern New England and includes some of the region’s highlights. If you are looking for more road trip ideas and want to dig a little deeper into New England, I’d recommend:

• New England road trips to take in the fall
• Vermont road trip itinerary
• Off-the-beaten path Maine road trip

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