road trip depart boston

New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , New York , Rhode Island , Vermont  ·  March 30, 2022

34 Awesome Road Trips From Boston & Best Itineraries (2024)

Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.

This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

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Best Road Trips From Boston

For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.

Best things to do in Plymouth:

• Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
• Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
• Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
• Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
• Walk around the charming downtown to visit the shops and restaurants,
• Pop into Dirty Water Distillery for an artisanal spirits tasting.
• Go on a whale watch tour with Captain John’s Boat Tours .
• Spend the day getting pampered at Mirbeau Resort & Spa , and even stay for lunch or dinner, or the night for the ultimate day of relaxation.

Click here to book your stay at Mirbeau Resort & Spa!

Psst! I have an entire post on visiting Plymouth, MA , if you need more ideas!

2. Cape Cod, MA

Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.

Best Things To Do on Cape Cod :

• Visit The Cape Cod National Seashore
• Explore Chatham’s downtown
• Visit Provincetown and the Pilgrim Monument
• For more on the best things to do on the Cape, click the link below for my detailed travel guide.

You may also enjoy:

• Can’t Miss Things To Do When Visiting Cape Cod For The First Time
• Best Things To Do On Cape Cod For Adults
• Best Towns To Stay In On Cape Cod
• What To Pack For Cape Cod
• Unique Things To Do On Cape Cod

3. Nantucket, MA

Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.

To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.

Best Things To Do on Nantucket:

• Explore the shops and restaurants in the main town.
• Visit Brant Point Lighthouse.
• Rent a moped to explore the local beaches and towns.
• For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
• The Best Nantucket Day Trip Travel Guide
• How Many Days Do You Need On Nantucket + Suggested Itineraries
• How To Visit All The Nantucket Lighthouses

4. Martha’s Vineyard, MA

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.

To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).

Best Things To Do on Martha’s Vineyard:

• Gingerbread Cottages in Oak Bluffs
• Edgartown downtown and lighthouse
• Aquinnah Cliffs and Gay Head Lighthouse
• South/Katama Beach
• For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.

You may also find these Martha’s Vineyard posts helpful:

• Is Nantucket or Martha’s Vineyard Better For A Day Trip?
• The Ultimate Martha’s Vineyard Day Trip Guide
• How To See Martha’s Vineyard Without A Car

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.

Best Things To Do in Marblehead, MA:

• Marblehead Lighthouse & Chandler Hovey Park
• Self-guided historical home walking tour.
• Take in the views at Castle Hill Rock.
• For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.

Click here to read even more awesome things to do in Marblehead!

6. Salem, MA

Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.

Best Things To Do in Salem, MA:

• Winter Harbor Park and Lighthouse
• Salem Witch Trials Memorial
• Salem Maritimes National Historic Site
• Essex Street Pedestrian Mall
• House of Seven Gables
• Peabody Essex Museum

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 😉

7. Rockport, MA

Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.

Best Things To Do in Rockport, MA:

• Visit Motif 1, the most painted building in New England, if not the country!
• Go for a scenic walk or hike at Halibut Point State Park.
• Meander through the shops on Bear Skin Neck.
• For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.

Click here for more amazing things to do in Rockport!

Click here to read my travel guide on the best things to do on Cape Ann!

8. Newburyport, MA

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.

Best Things To Do in Newburyport, MA:

• Visit Oldies Marketplace to look for antiques and treasures.
• Meander the streets of downtown to explore the beautiful storefronts.
• Take a leisurely stroll along the waterfront park.
• Pack a picnic or take a nature walk at Maudslay State Park , which has over 500 acres to explore.
• Head out on the open waters with Yankee Clipper Tours , and cruise around the Merrimack River and Newburyport Harbor.
• Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co. , and walk the stunning nature trails at the Parker River National Wildlife Refugee .

Click here to read my full guide to visiting Newburyport & Plum Island!

9. Block Island, RI

Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.

Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.

It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.

To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here .

Best Things To Do on Block Island, RI:

• Take in the views at Mohegan Bluffs.
• Rent a moped to explore the entire island.
• Spend some time swimming at Mansion Beach.
• Visit the island’s two lighthouses.
• Have lunch with a water view at The Oar .

Click here to read all my tips for taking a Block Island day trip!

10. Newport, RI

Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.

With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.

Best Things To Do in Newport, RI:

• Walk along Cliff Walk for amazing coastal views.
• Visit Bowen’s Wharf for shopping and dining.
• Grab a lobster roll at the Newport Lobster Shack .
• Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
• Sail around Narrangansett Bay with Sightsailing of Newport .
• Visit the unique shops along Thames Street.
• Grab lunch and cocktails at The Lawn at Castle Hill Inn , overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!

Click here to book your stay at The Castle Hill Inn in Newport .

Click here to read all my tips for taking a Newport, RI day trip!

Click here to read about all the best things to do in Newport, RI in the winter!

11. Mystic, CT

Distance From Boston: 1.5 hours

This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.

Best Things To Do in Mystic, CT:

• See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium .
• Learn all about maritimes history at the Mystic Seaport Museum and Village , which is regarded as one of the best, if not the best, Maritimes museums in the country.
• Hit the trails at Bluff Point State Park.
• Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters .
• Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.

Click here to read about all the best things to do in Mystic, CT!

12. The Hamptons, NY

Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.

The Best Things To Do in The Hamptons:

• Have a beach day and watch the surfers at Coopers Beach in Southampton.
• Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
• Take in the views at Montauk Lighthouse.
• Enjoy an afternoon of rest and restoration at the Montauk Salt Caves .
• Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
• Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer , but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.

Best Things To Do in Ogunquit, ME:

• Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
• Visit Perkins Cove to enjoy its charming shops and restaurants.
• Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
• For more information on things to do in Ogunquit, click the link below for my detailed travel guide.

Click here to read about more amazing things to do in Ogunquit!

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.

Best Things To Do in Kennebunkport, ME:

• Visit Gooch’s Beach for a walk along the shore, or go for a swim.
• Have an authentic lobsterman experience with Rugosa Lobster Tours .
• Walk around the downtown and Dock Square shops.
• Grab an artisanal ice cream cone at Rococo Ice Cream .
• Have some craft cocktails and beer at Batson River Brewing and Distillery .
• Walk along Parson’s Way for amazing views of the dramatic coastline.
• Grab fresh seafood takeout from The Clam Shack .

Click here to see why Kennebunkport is one of the best Christmas towns in New England!

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.

Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.

Best Things To Do in Bar Harbor & Acadia National Park:

• Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
• Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
• Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
• Explore Bar Harbor’s downtown.
• Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
• Visit Bass Harbor Lighthouse inside Acadia.

Tip : You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here .

Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary , and the Best Time To Visit Acadia National Park .

Luxury Road Trip Destinations From Boston

These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.

16. Cliff House in Cape Neddick, ME

If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.

What To Expect During Your Stay At Cliff House:

• Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
• Complimentary coffee, tea and water stations on each floor.
• A full-service spa.
• Three oceanfront restaurants and a coffee cafe.
• Manicured gardens and pathways for relaxing walks.
• Two outdoor pools, two indoor pools and a hot tub.
• On-site shopping.

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.

What To Expect During Your Stay At Ocean House:

• Freshly designed and elegant coastal New England rooms and suites.
• Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
• Complimentary activities within the resort, such as daily yoga and cooking classes.
• Valet parking included in your room rate.
• Four on-site restaurants, and lobster dinners on the lawn during the summer.
• An on-site spa.
• Beautifully manicured lawns with yard games.
• Complimentary refreshments throughout the day.

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.

Overviews of the resort have been used in the Amazon Prime series Upload , and has long been rumored to be the inspiration behind Stephen King’s The Shining . But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.

If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.

What To Expect During Your Stay At Mohonk Mountain House:

• Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
• Lake Mohonk on the resort grounds.
• An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
• 85 miles of hiking trails right outside your door.
• Farm-to-table dining.
• Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.

Click here to book your stay at Mohonk Mountain House!

Click here to read my detailed review of a Mohonk Mountain House Day Pass!

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.

The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.

What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:

• A serene, calm spa atmosphere throughout the entire grounds.
• A relaxation room, aqua terrace and steam facility within the spa.
• Different spa packages to customize your stay that include dining options to make your visit stress-free.
• Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.

Best Things To Do in Saratoga Springs, NY:

• Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
• July – Labor Day, visit the Race Track , and even try your hand at placing bets on the winner!
• Stroll through Congress Park, and find the mineral springs to taste the local water.
• Enjoy a healing bath at the Roosevelt Baths & Spa . The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
• Take in a live show at SPAC , one of the the country’s most renowned outdoor concert venues.
• Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
• Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.

Click here to book your stay at the Adelphi Hotel in Saratoga Springs!

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.

Best Things To Do in Skaneateles, NY:

• Walk around Main Street to visit the boutiques.
• Sit and admire the views of the lake from the town’s many waterfront areas.
• Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
• Head out onto the lake for a boat tour.
• Grab dinner and drinks at the Sherwood Inn , located right in the heart of town, and just across the street from the lake.
• Spend the day getting pampered at Mirbeau Inn & Spa , the original Mirbeau location, which is home to a Monet-inspired garden and bridge.

Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!

Click here to read more suggestions on the best things to do in Skaneateles, NY!

22. Lake Placid, NY

Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.

Best Things To Do in Lake Placid, NY:

• Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
• In the winter, enjoy skiing at Whiteface Mountain , and ice skating and a Toboggan Chute on Mirror Lake.
• Enjoy the miles of hiking trails in the nearby mountains.
• Walk around the alpine-inspired downtown village to visit the quaint shops.
• In the summer, go for a swim in Mirror Lake from the public beach area.
• Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum .
• Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
• Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!

Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid .

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

You may also like:

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• Best Day Trips From Portland, Maine
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• Best Things To Do In New England For Your Bucket List

32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

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That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

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Best Road Trips From Boston

Top road trip destinations from boston.

Niagara Falls

🚗 470 miles ⏱️ 7 hours

No matter what time of the year you visit Niagara Falls, you will fall in love with its majestic scenery. If you travel during the warmer months, you can take a boat tour to see the raw power of nature up close.

Get ready to explore beautiful cities and landscapes in Upstate New York as you drive past Albany , Syracuse , Finger Lakes and Buffalo en route.

New York City

🚗 215 miles ⏱️ 4 hours

If one city has something unforgettable for every type of traveler, it is the Big Apple. Spend some time at Times Square, explore world-class museums, enjoy Broadway shows and visit the iconic landmarks.

This drive features a great mix or urban and natural, and you can visit places such as Wells State Park , Wadsworth Atheneum Museum of Art in Hartford and New Haven en route.

Portland, Maine

🚗 110 miles ⏱️ 1 hour, 50 minutes

Portland is a coastal gem known for its lighthouse-dotted landscapes. From strolling along the cobblestone streets of the Old Port to treating yourself to fresh seafood and craft beer, Portland is the quintessential New England town.

En route, you will find plenty of amazing new places to discover on the coast, such as Maudslay State Park , Portsmouth Market Square and the cute towns of York and Ogunquit .

Acadia National Park and Bar Harbor

🚗 320 miles ⏱️ 6 hours, 30 minutes

Acadia National Park is one of the most-visited parks in the country and it is easy to understand why. Hike granite peaks, bike historic carriage roads, and witness sunrise at Cadillac Mountain where the mountains meet the sea.

This drive is a feast for the eyes with endless coastal scenery in Portsmouth , York , Ogunquit and Portsmouth as well as a dip inland to visit the beautiful town of Augusta .

Washington DC

🚗 440 miles ⏱️ 7 hours, 40 minutes

A visit to Washington DC, is a must for any history buff. Here, you can tick iconic landmarks off your bucket list, such as the Lincoln Memorial, the Smithsonian Museums, and the White House.

Some of the charming New England towns you can visit en route include Hartford and New Haven as well as iconic cities such as New York and Philadelphia .

Cape Cod and Provincetown, Massachusetts

🚗 120 miles ⏱️ 2 hours, 20 minutes

Cape Cod and Provincetown are amazing summer destinations. Known for its stunning beaches, historic lighthouses, and buzzing arts scene, this picturesque peninsula is also a great place to enjoy whale watching from mid-April to October.

You can expect some inspirational oceanside scenery on this drive, and visit Plymouth , Sagamore Beach , Nickerson State Park and Cape Cod National Seashore .

Philadelphia

🚗 400 miles ⏱️ 7 hours, 10 minutes

If you have spent some time in the US, it is likely that you are familiar with the Liberty Bell and Independence Hall in Philadelphia. Come here for history, and you will end up staying for the eclectic neighborhoods and the famous Philly cheesesteak!

You will drive past a beautiful stretch of New England on this drive, and get to spend time at Providence and New Haven , followed by a quintessential visit to the Big Apple .

🚗 50 miles ⏱️ 1 hour

If you are looking for the perfect blend of historic charm and modern sophistication, Providence is the perfect destination from Boston. Make sure to enjoy a scenic walk around the WaterFire art installation.

Even though this is a relatively short drive, there is plenty to see en route, such as the Quincy Quarries Reservation , Blue Hills Reservation and the beautiful F. Gilbert Hills State Forest .

Quebec City

🚗 390 miles ⏱️ 7 hours, 40 minutes

For a slice of Europe in North America, Quebec City is a UNESCO World Heritage site famous for its fortified colonial core and stunning Château Frontenac. Here, you will enjoy the French heritage of the city and its delicious cuisine.

This cross-border adventure will take you past Portsmouth , Portland and Augusta before you cross into Canada to visit Saint Georges before you reach your destination.

🚗 600 miles ⏱️ 9 hours

Discover Toronto, Canada's largest city! From its easily recognizable CN Tower to its bustling markets, expansive green spaces, and waterfront districts, you will find plenty to do in this charming city.

Before you travel across the border into Canada, you can visit the New York State Capitol in Albany and Saratoga Springs , as well as Kingston and Oshawa once in Canada.

🚗 985 miles ⏱️ 14 hours, 50 minutes

You will immediately recognize the famous Chicago skyline as you approach the Windy City, full of Midwest charm. Dive into the city's jazz and blues scene, savor deep-dish pizza, and visit iconic sites like Millennium Park.

En route you will drive through many iconic cities on this drive to Chicago, such as Albany , Syracuse and Cleveland as well as visit the Finger Lakes .

🚗 300 miles ⏱️ 4 hours, 45 minutes

A relatively manageable drive across the Canadian border and you will find yourself in Montreal, home to the historic streets of Old Montreal and Mount Royal Park, which features stunning views and snowshoeing and tubing in winter.

Driving north to Canada, you will get to visit Montpelier and Burlington in Vermont, which is particularly beautiful in the fall, before crossing the border.

Nova Scotia

🚗 660 miles ⏱️ 14 hours, 30 minutes

Nova Scotia is located where the Atlantic Ocean meets rugged coastlines and jaw-droppingly beautiful landscapes. Another destination where you can admire historic lighthouses and indulge in fresh seafood.

This drive will take you past one coastal view after another such as in Portland , Bar Harbor and stunning Acadia National Park before you reach Canada.

Myrtle Beach

🚗 930 miles ⏱️ 17 hours, 10 minutes

Head to Myrtle Beach for a fun-filled getaway in the heart of the Grand Strand. Enjoy miles of sandy beaches, amusement parks, and live entertainment. This family-friendly destination offers something for everyone.

There are plenty of amazing places to visit on this route, such as New York , Philadelphia and Virginia Beach . You can also see the wild horses of Chincoteague National Wildlife Refuge .

🚗 730 miles ⏱️ 12 hours, 20 minutes

Raleigh is the capital of North Carolina, known for its pretty parks, and historic sites. When in Raleigh, we recommend visiting the North Carolina Museum of Natural Sciences and strolling through the beautiful Pullen Park.

This drive is an urban adventurer's dream with New York , Baltimore and Washington DC directly en route. You can also make a detour to Richmond .

Longer road trips from Boston

🚗 1,400 miles ⏱️ 23 hours, 40 minutes

From the magic of Walt Disney World to the popular rides of Universal Studios, Orlando offers endless fun for families and visitors of all ages.

🚗 1,580 miles ⏱️ 25 hours

Soak up the sun in Miami, famous for its stunning beaches, and glitzy nightlife. During the daytime, you can enjoy a tour to view the Art Deco buildings of South Beach.

Los Angeles

🚗 3,115 miles ⏱️ 48 hours

Famous for its iconic Hollywood Sign, always-busy Venice Beach, and glamorous Rodeo Drive, Los Angeles is one of the best destinations on the Pacific Coast.

Road Trips from Boston – 42 Best & fun getaway ideas for your Massachusetts scenic drive

Road Trips from Boston – Best & fun getaway ideas for your Massachusetts scenic drive

Looking to spice up your Boston adventure with an escape from the city? Lucky for you, there are plenty of thrilling road trips from Boston that you and your family and friends can hop on to and enjoy!

So, if you find yourself looking for ‘Boston getaway’, ‘best road trips from Boston’, or ‘ fun road trips near me’, then buckle up!

Drive through majestic mountains, breathtaking National Parks, and picturesque skiing destinations, or hit the coast for a seaside adventure through charming towns and villages as you take on your next Boston road trip with the help of your list of road trips from Boston ideas!

With endless options for exploration, your Boston road trip can take you on a journey of a few days or more. So sit back, relax, and let us guide you to the most unforgettable road trip experiences departing from Boston!

Editor’s Note:  Our staff works hard to bring you the latest information. However, all information mentioned in this article is subject to change. As always, please confirm before heading out.

Also check our posts on  Best Parks In Boston ,  Things To Do In Boston This Weekend ,  Outdoor Activities Boston , and  Free Museum Days In Boston !

Get the lowest price on the very popular Boston Hop On Hop Off Trolley Tour 

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.

Board one of the orange-and-green trolleys at any of the stops and enjoy the view with live commentary from an expert guide who knows the city inside and out. Learn about the history and happenings of Boston, a city known as the Cradle of Liberty, as the trolley rolls along from one location to the next. For one, or two consecutive days, hop off at any of the attractions for a closer look, then hop back on when it’s convenient.

14 stops and 33 points of interest!

Get all the details and book your Boston Hop On Hop Off Trolley Tour  TODAY!!!

Road Trips from Boston – Scenic drives 2023

Mohawk trail, ma.

If you’re looking for scenic drives from Boston, the Mohawk Trail is the way to go. This 69-mile scenic route passes through deep forests and historic towns. You’ll be passing world-class art museums, early 20th-century tourist destinations, scenic hikes, and dramatic vistas. All the while, you’ll also be crisscrossing and paralleling five major rivers—the Millers, Connecticut, Green, Deerfield, and Hoosic. It’s quite the scene alright.

Driving time:  2 hours

Martha’s Vineyard, MA

Road Trips from Boston | Image credit: Visit Martha’s Vineyard

Getting to Martha’s Vineyard might not take the whole day, however, for you and your companions to fully enjoy your road trip there, an overnight stay might be better. There, you can take a scenic drive through any of the island’s six beautiful towns. Enjoy the sights of dramatic cliff-lined shores or shop in their quaint Main Street.

Driving time:  2 – 3 hours

Provincetown, MA

For a Boston scenic drive, head on over to Provincetown. This quirky town at the tip of Cape Cod boasts art galleries, beaches, and a vibrant LGBTQ+ culture. It’s also the kind of town where you can indulge in a bottomless brunch right before you head out to see the Pilgrim Monument on the spot where the Mayflower Pilgrims first set foot in the New World.

Driving time: 2 hours and 14 minutes

Lake Winnipesaukee, NH

Lake Winnipesaukee is the biggest lake in New Hampshire. And it’s a picture-perfect summer destination for locals and tourists alike. It’s a great Boston getaway destination if you and the family are into boating, fishing, and water sports.

Driving time: 2 hours

Kancamagus Highway, NH

Road Trips from Boston | Image credit: White Mountains New Hampshire

One of the best scenic drives from Boston you can take is through the Kancamagus Highway. It’s known as one of the best Fall Foliage viewing areas in the country. In addition to that, it takes you through the White Mountains which is a great place for hiking trails, mountain views, and spectacular waterfalls.

Driving time: 2 hours and 8 minutes

Franconia North State Park, NH

Enjoy the beautiful outdoors at the Franconia North State Park for your Boston road trip. This scenic park is perfect if you’re looking to enjoy a bit of everything to do with the outdoors including hiking, biking, fishing, and swimming. 

Acadia National Park, ME

Road Trips from Boston | Image credit: Acadia National Park

If you’re looking for a little more thrill and adrenaline rush for your outdoor activities, check out the Acadia National Park for your Boston to Maine road trip. This park has a huge focus on adrenaline-pumping activities like biking, hiking, rock climbing, and horseback riding. 

Driving time: 4 hours and 33 minutes

Road Trips from Boston – Places to go within 3 hours

Image credit: Destination Salem, Massachusetts

Just by its name, you might have had a hint that this coastal town is the premiere destination for all things spooky. Visiting it in October for its vibrant Halloween season is definitely a great to-do for your Boston road trips. But it’s also a great place to visit all year round with plenty of museums and trial sites to check out.

Driving time: 30 – 40 minutes

Plymouth, MA

If you’re looking for a quick and easy Massachusetts road trip, Plymouth would be a fun way to go. It’s known as America’s Hometown and is filled with a rich history. With that, you’ll see plenty of historical markers and historic buildings. Aside from that, there is also plenty of outdoor activities, parks, and beaches worth seeing.

Driving time: 40 – 50 minutes

Gloucester, MA

Gloucester might be the most authentic and picturesque fishing centers you’ll ever have the privilege of seeing. “America’s Oldest Seaport” also doubles as a center for painting and printmaking and an haven for the arts. A little outside the main stretch, check out Dogtown Commons for some of the most unique walking trails in the country.

Driving time: 42 minutes

Rockport, MA

Road Trips from Boston | Image credit: Rockport USA

Rockport is a picturesque seaside town with art galleries, beaches, and seafood restaurants. Despite being a small town, it has plenty of character and would really invite you to slow down from the bustling Boston lifestyle. A day or two here would truly relax and refresh you.

Driving time: 50 – 60 minutes

Cape Ann, MA

Cape Ann might not be as glamorous as Cape Cod but it’s still a place worth visiting. You can check out quaint little villages straight out of a movie set and fill up on delicious lobster served in so many ways. It’s also a great place to relax away from the fast life of the city.

Driving time:  52 minutes

Take a trip to Lowell and explore the historic mills which once powered this country’s textile industry. Check out The Boott Cotton Mills Museum, National Streetcar Museum, and The New England Quilt Museum. And get lost in the booming arts scene at the local favorite Mill No. 5 converted mill.

Driving time:  34 minutes

Providence, RI

Image credit: GoProvidence

Providence is home to famed schools Brown University and the Rhode Island School of Design. But if you’re not there for the education, that’s okay too because Providence is actually a fun place to be a tourist in. With tons of restaurants, shops, nightlife, and history to check out, this city makes for an amazing road trip from Boston.

Driving time:  1 hour

Portsmouth Harbor Lighthouse

Road Trips from Boston | Image credit: Friends of Portsmouth Harbor Lighthouses

Portsmouth Harbor Lighthouse is a great place to go if you’re looking for great ocean views. The historic lighthouse offers tours and spectacular views of the Atlantic Ocean. You’ll also get a bird’s eye view of Fort Constitution, which is situated adjacent to the lighthouse, as well as the opportunity to admire the lighthouse’s working fourth-order Fresnel lens up close.

Driving time:  1 hour and 9 minutes

Ogunquit, ME

One of the best Boston to Maine road trips you can take is to Ogunquit, a beach town that will surely delight beach lovers. It has both sandy beaches perfect for swimming and dramatic and rocky coastlines great for sightseeing. And once you get there, you can get almost everywhere on foot making it a perfect short but sweet getaway.

Driving time:  1 hour and 15 minutes

Nubble Lighthouse, ME

Cape Neddick Lighthouse, also known as Nubble Lighthouse, is one of Maine’s most popular attractions. And it’s definitely worth visiting on your road trip from Boston. Here, you’ll get to see the beautiful local scenery, get amazing views from the park, and explore the lighthouse’s rich history.

New Port, RI

Road Trips from Boston | Image credit: Discover Newport

New Port is also called the Sailing Capital of the World and the Queen of Summer Resorts. So there you have it in a nutshell. The best part is that it’s technically a city so you can have fun at the beach and enjoy all it has to offer while still getting the convenience a city has to offer. 

Driving time:  1 hour 30 minutes

Road Trips from Boston | Image credit: Mystic Aquarium

This adorable little town has a great mix of nature, small-town charm, and maritime history. Go on sunset or moonlit cruises or grab a warm delicious lobster roll. You can also check out the Mystic Aquarium where you’ll see beluga whales, penguins, sharks, and sea lions. This is a great Boston getaway if you simply want to chill.

Portland, ME

Road Trips from Boston | Image credit: Visit Portland Maine

Portland is a vibrant coastal city that provides the best of both worlds for being a city and coastal destination. Enjoy everything here from a dramatic coastline to their amazing food scene on your road trip from Boston with friends or family.

Driving time:  1 hour 45 minutes

Cape Cod, MA

Cape Cod is the ultimate beach getaway Boston road trip. With over 15 towns for you to choose from to visit and over 500 miles of shoreline to explore, you’ll feel like you’re in a whole other world. Fill your time checking out beautiful little coastal towns, eating fresh seafood, enjoying the cool waters, and gazing at beautiful sunsets. 

Ipswich, MA

Ipswich is the perfect place for nature lovers out there. It boasts beautiful vast open spaces and beautiful waters where you can go canoeing or boating. The town also has fantastic trails and state parks where you can bike, hike, and walk.

Driving time:  46 minutes

Newport Vineyards, RI

Road Trips from Boston | Image credit: Newport Vineyards

If you are fond of wines and great food, the Newport Vineyards is a destination you must pass by on your road trip from Boston. This winery provides tastings and tours. They also have a farm-to-table restaurant where you can enjoy the very best of the produce of the area. It’s a perfect getaway for couples or friends looking to spend intimate time together.

Driving time:  1 hour and 16 minutes

Burlington, MA

From incredible shopping and famous local restaurants to history, art, and exciting sports, you’ll find local New England culture surrounding you in Burlington. Here, you’ll be able to find a bit of rest and a slower pace from the big city. 

Marblehead, MA

Marblehead would just be a quick Boston scenic drive. Situated along the North Shore of Massachusetts, this place is filled with small-town charm, dramatic, rocky coastlines, options for beaches, great seafood, and historical homes. It’s the perfect place to lay back with the family.

Portsmouth, NH

If you’re looking for a place with character to go to for your Boston road trips, you should definitely check out Portsmouth. It’s a city but it feels more like a cozy little town. Here, you’ll find plenty to check out with their quaint shops and boutiques. It’s also known as a huge foodie destination. 

Brattleboro, VT

Boston already has a thriving arts scene but another place where you can enjoy a blooming arts community is the town of Brattleboro in Vermont. This town has a great arts and culture scene and a big part of that is the Brattleboro Museum & Arts Center. Aside from checking out their museums, you can also grab some fresh produce at their farmer’s markets and go on a shopping spree at their shopping alleys.

Woodstock, VT

Woodstock has that perfect New England charm and while it’s a favorite place for tourists because of that, it also doesn’t lose its local character. It’s also the kind of idyllic town that writers write about. Here, you can lay back, relax, and simply enjoy small-town life. Walk through the quaint neighborhoods, check out the orchards and farms, or simply check out the local cafes and shops. 

Driving time: 2.5 hours

North Conway, NH

North Conway is a great Boston getaway to step back from the busy life of the big city. You can shop tax-free at the North Conway Settlers Green Outlet Village, see a play at one of the area playhouses, take a scenic ride and a dip in the cool mountain waters, or grab a souvenir from one of the local hand-craft, antique and gift shops.

Driving time: 2 hours and 33 minutes

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Road Trips from Boston – Destinations between 3 to 10 hours

Manchester, vt.

Road Trips from Boston | Image credit: Visit Manchester

If you’re looking to disconnect and relax for a moment, head on over to Manchester, Vermont for your road trip from Boston. From everywhere here, you’ll be able to see tall mountain peaks. And there are various outdoor activities waiting for you. These include hiking the Lye Brook Falls trails, hiking or driving up Mt. Equinox, the tallest mountain in the Taconic Range, or going for a dip in the Dorset Marble Quarry.

Driving time:  3 hours and 10 minutes

Niagara Falls, NY

Road Trips from Boston | Image credit: Niagara Falls Tourism

If you’re going to New York for your Boston road trip, then you might as well pass through these world-famous waterfalls. Go on a boat tour and feel the splash of the waterfalls or stay on the observation deck to take in the views. You can also check out Niagara-on-the-Lake, a quaint Canadian town known for its wineries, theaters, and historic sites. 

Driving time:  7 hours 

Green Mountains, VT

For those up for a little more adventure, take your Boston road trip to the Green Mountains of Vermont. In the winter, there are three ski resorts you can visit to enjoy plenty of skiing and other wintertime activities. In the summer, you can enjoy hiking along some of the most famous trails in the country. Both the Appalachian Trail and the Long Trail pass through the area and share the route over a stretch of 100 miles

Driving time: 3 hours and 47 minutes

Bennington, VT

Bennington is a historic town and a great place to pass by on your Boston road trip. Check out historic sites, museums, and art galleries, and take a quick tour of the past while appreciating your history. You can also visit the Bennington Battle Monument and take a few snaps along the way.

Driving time: 3 hours and 7 minutes

Montreal Botanical Garden, QC

The Montreal Botanical Garden is for the avid plant lover. The garden has a rich collection of 22,000 plant species and cultivars. And they’re distributed throughout 10 exhibition greenhouses and some 30 thematic gardens which make the destination all the more spectacular. It’s a great place to stop by for families who’re looking to stretch their legs and enjoy wonderful sights.

Hudson Valley, NY 

Hudson Valley has a reputation for being incredibly charming. And it’s an amazing place to relax and simply see where the day goes. For suggestions, you can go antiquing, take a boat cruise, explore the local galleries, check out the wineries, tour the historic mansions, and do plenty of other outdoor activities.

Driving time: 3 hours and 18 minutes

Road Trips from Boston | Image credit: Go Stowe

Head on over to this picturesque mountain town for your road trip from Boston for tons of outdoor fun. In the winter, it’s a well-known ski destination. And in the warmer months, you can switch out skiing for hiking and sightseeing for some of the town’s fantastic covered bridges.

Driving time: 3 hours and 20 minutes

New York City, NY

Image credit: Times Square, New York City

New York City is known for many things and much like Boston, it’s a place to be for many young people right now. However, it’s most known for its artistic prowess and the talents it holds. Unlike any other place in the world, stepping into the entertainment scene here would feel completely different. Aside from that, you can enjoy the history of the city, its museums, the food scene, and the stunning galleries.

Driving time: 4 hours and 16 minutes

Philadelphia, PA

If you’re interested in taking a city break while appreciating American history right where a lot of it happened, taking your road trip from Boston to Philly is the way. The City of Brotherly Love is deeply rooted in history and has plenty of places where you can soak it all up. Aside from that, there are all kinds of things to check out from exciting nightlife and amazing food to parks and waterfront activities.

Driving time: 5 hours

Montreal, QC

Being the second largest city in Canada, Montreal boasts plenty of attractions for everyone to enjoy. For one, you should check out the historic architecture. Then, you should check out the festivals. Here, there is a festival for almost every main music genre out there. And, of course, don’t forget to explore the food scene. The cuisine in Montreal is extremely diverse and dishes here will be like nothing you’ve ever tasted before.

Driving time: 5 hours 

Montauk, NY

Image credit: Visit Montauk

For scenic drives from Boston, heading to Montauk is a great one. On the way, you’ll be able to pass beautiful sights. And when you get to the coastal town, you’ll be greeted with beaches, lighthouses, and a cozy summer vibe. You can also find hiking trails, music and art festivals, seafood restaurants and more to enjoy. For the kids, there are plenty of fishing, surfing, and padding activities to enjoy.

Driving time: 5 hours and 12 minutes

Toronto, ON

From one city to another. Get a feel of what city life is like in another corner of the world in Toronto. This city has something for everyone. For those that love nature and outdoor activities, you’ve got Toronto Islands and the parks. For those that love sports, you have Scotiabank Arena, Rogers Center, and more. There are also beaches and plenty of museums for families. Make sure to give the city time though so you’ll be able to make the most of your time there.

Driving time: 8 hours and 40 minutes 

Quebec City, QC

Image credit: Québec cité

The historic heart of Quebec City is a UNESCO World Heritage site and here, you can soak up its storied past and European charm. More than that, the fun never stops in Quebec. With a steady string of events all year round including historical festivals, theatrical happenings, and sports events, there are always tons of things to do and see. It’s also a foodie destination known for its wide range of styles with French, British, North American, and Indigenous influences. The road trip from Boston may be long but it’s one worth taking.

Driving time: 6 hours and 13 minutes

Do you have any other fun road trips from Boston ideas? Share them with us in the comments!

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16 Fun Road Trips from Boston Only A Short Drive Away

One of the best things about taking a trip to Boston is that there’s so much to do and it’s all so easy for you to get to. You can even take a day trip to New York and head back for the evening without having to worry about losing too much time!

In fact, arguably, the biggest challenge with planning a trip from Boston is narrowing down potential destinations. Plus, there’s an international airport to consider and the option of taking a cruise from Boston to see some of the world from the sea.

Here are a few of the destinations just a short drive away from Boston that you’ll want to consider, whether you’re a Boston resident or looking to book your next road trip. Pack some snacks for the family and hit the road!

This post is part of our North American Destinations Series – you can also read more great road tripping with kids ideas here

Trips from boston: a short drive away, 1. plymouth.

Plymouth, Massachusetts, shares its name with an old English seaside town, and it’s mostly known as the spot where the Mayflower docked and established a colony 400 years ago. There’s plenty of old architecture and historical monuments around Plymouth to see, and it also has a bunch of awesome museums and restaurants to visit.

Plymouth is particularly magical around Christmas, making it one of our favorite winter destinations in the US .

No, this isn’t a typo, and you’re not going crazy. Plimoth Plantation is a sort of living exhibit where you can walk around at your leisure and experience what life would have been like as one of the pilgrims who first settled there.

This is especially a great option if traveling with kids. Many of the original machines and technologies were around at the time, making it a great way to learn a little more about history and where we all came from.

Check out these incredible Airbnb properties around New England to complete your road trip!

3. Portsmouth

Okay, now we’re just playing with you. Don’t make the mistake of getting these three very different destinations confused with each other. This coastal city is also named after an English counterpart, and it’s a great spot for everything from boat trips and fresh seafood to museums and theatres.

Better still, it’s been growing and growing in recent years and now has the infrastructure to rival anything that any other city can throw at it.

4. Newport

Also named after a British place (this time in Wales), Newport is another stunning little coastal town with plenty to offer the casual visitor. In particular, we’d recommend strolling through Brick Market Place in the city’s downtown area, which is iconic for its delicious Chinese cuisine and the wide range of shops and stores that are on offer.

The Newport Mansion at Christmas is an unforgettable experience. And if you’re a car lover, you’ll want to stop by Portsmouth (also on this list) to visit the Newport Car Museum.

5. Newburyport

Seriously, what is it with these names? This coastal town has a lot in common with some of the others on this list, except that it’s a little less busy and so it’s easier for you to lose yourself in your own thoughts while wandering around the stunning scenery.

If you can get there in the summer, all the better – the street performers will be out in full force and the beaches will be just right for a bit of sunbathing. For a small town, there’s a lot to see and do in Newburyport .

6. Lincoln

Nestled at the base of the White Mountains in New Hampshire , there’s plenty to see and do in Lincoln throughout the year. In the winter, the town really comes alive, with a range of winter sports available as well as some of the most scenic ice skating rinks that we’ve ever come across. It’s a great place to take the kids if you’re looking for something magical in the run-up to Christmas.

7. Cambridge

Are you starting to see a theme here? Also named after our friends across the pond, Cambridge MA is just as intellectual as its British counterpart. As the home of Harvard, it’s also home to a bunch of different art galleries and museums that will satisfy even the most culture-obsessed travelers. And because even the smartest college students know how to party, there’s also plenty going on in the nighttime.

8. Providence

Located in Rhode Island, Providence is about an hour’s drive from Boston and makes for a great day trip if you want to see something a little bit different. It has regular festivals and celebrations throughout the year, so if you’re thinking about swinging by then it can be a good idea to spend some time looking at what’s coming up on the calendar; fall is a busy time with leaf-peeping road trippers in New England!

You’ll find plenty of fantastic places to eat, too. We recommend scoring some Italian food on Federal Hill.

9. Martha’s Vineyard & Nantucket

Martha’s Vineyard is one of only five US place names with apostrophes in the name, something which is technically against the law . In fact, it’s only been allowed to keep it because it has so much history, and that should give you a clue about why you might want to visit Martha’s Vineyard in the first place. And as you might expect from a place named after a vineyard, the food and drink scene is fantastic .

Nearby, Nantucket Island is known for its stunning beaches , picturesque lighthouses and crashing Atlantic waves.

10. Provincetown

Based on Massachusetts’ iconic Cape Cod , Provincetown is reminiscent of San Francisco in many ways because it’s a haven for artists, actors, musicians, and more, as well as a thriving LGBTQ+ community.

There are museums and art galleries almost everywhere you turn, as well as cool specialist stores and boutiques selling handmade goodies. There’s really nowhere else in Massachusetts that’s quite like it, and it’s sure to have something for everyone in the family.

11. New York City

As we mentioned earlier, New York City is just 4 hour’s drive away, and the city that never sleeps has so much going on that you could spend a month there and not run out of things to do.

Still, you can see quite a lot in a day trip or even spend the night there to give you a little more time – there’s plenty to see and do on the drive from Boston to New York City too; we’d strongly recommend extending your trip through Upstate New York .

You can read our family guide to exploring Manhattan here .

12. Castle Hill

You’d be crazy to skip a visit to this stunning 60-room mansion. You’ll feel as though you’ve stepped out of Massachusetts and into the middle of the English countryside. At only an hour’s drive away, it’s perfect for a half-day out. Pack a picnic and a blanket to enjoy lunch on the lawn.

13. Glendale Falls

Glendale Falls offers a great excursion by providing you with some of the most awe-inspiring natural beauty the state has. It’s one of the largest series of waterfalls in the country, and there are many trails to explore.

15. Concord

Concord is a relatively small town with a big history. It’s probably most well-known for being the site of a number of battlefields and as the haunting grounds of several key figures throughout history, including writers and statesmen. Walking through Concord, you know you’re retracing famous footsteps.

16. Lexington

Lexington is known for its battlefields too, including the iconic spot on Lexington Common where soldiers fired the first shot of the Revolutionary War. Many come in droves to learn more about the history of the area and the stunning country that we live in today. 

Want to extend your trip even further to Acadia National Park and the Maine coast? Try this road trip itinerary taking you all the way from Boston to Bar Habour on an epic new England Family road trip.

Planning your Boston day trips

Now that you know a few of the best places to visit while driving from Boston, it’s time for you to start planning your vacation. Remember, you can always combine multiple different destinations into a single trip by renting a car and going from city to city.

Because of that, it’s a good idea for you to go ahead and create a shortlist and an itinerary of your own, planning out where you’re going to visit, how long you’re going to stay, and which route you’re going to take.

By creating an itinerary and sticking to it, you can start to reserve hotels and other amenities to take advantage of early-bird pricing. This will save you money and also help you to avoid stressing too much in the run-up to your vacation. That way, you can just focus on having a fantastic time. Happy travels!

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Travel and Blossom

A travel and lifestyle blog for female solo travelers who want to learn how to travel with confidence

30 Best Road Trips From Boston

Fall Travel , North America , Spring Travel , Summer Travel , Winter Travel / April 2, 2022 by Jade / 16 Comments

Planning a road trip from Boston and don’t know where to go? Check out this post on the 30 best road trips from Boston.

As someone who doesn’t know how to drive yet, I’ve been dying to do a road trip out of Boston for quite some time now. However, until I’m able to get my license, my dream road trip out of Boston will have to wait. So, instead of pouting about as I wait for my license, I’d rather take this time to tell you some of the best road trips you can take out of Boston.

Table of Contents

New England Bucket List Series

P.s. this is a post in my new england bucket list series. here is the complete series:.

Road Trips: 30 Best Road Trips From Boston

Ice Skating: The Top 7 Places for Free Ice Skating in Boston

Hiking: 20 Best Hikes for Fall Foliage in New England

Fall Foliage: 12 Best Places for Fall Foliage in Boston

Thrift Stores: The 7 Best Thrift Stores in Boston for Vintage

Salem: One Day in Salem Massachusetts: Hocus Pocus Edition

Museums: The Top 8 Free Museums in Boston for College Students

Newport, RI (best road trips from Boston)

A trip to Newport, RI is one of the best road trips you can take out of Boston! The road trip will take about 90 minutes by car and there are a lot of fun things to do ! In fact, according to Pamela, Aquidneck Island is also home to Newport! In the island, you will find a lot of breathtaking sea cliffs around the Cliff Walk. The Cliff Walk is a 3.5 mile walk around the shore that shows off the breathtaking views of the mansions and the area. The Breakers is one of the most famous mansions around the area and it has tours available all year round .

Newport is also most popular during the summer due its wide range of water-based activities. Boats line the water all around Newport, and sailing is a common pastime in the area. However, if you’re visiting during the spring or fall, the nature’s colors will also inspire you!

The Naval War College Museum is also worth checking out if you’re looking to learn more about Newport’s history. Bowen’s Wharf and its neighbor Bannister’s Wharf , are even home to a variety of locally-owned shops and restaurants!

Overall, the elegant blend of history, nature and food is what makes Newport a great road trip to take from Boston.

By: Pamela of Directionally Challenged Traveler

Portland, ME (best road trips from Boston)

A trip to Portland, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 45 minutes to complete and you can do a lot of fun things while you’re there .

In fact, according to Kelly, while the fastest way to get to Portland from Boston is via I-95, this highway can often become inundated with traffic once in a while. Therefore, if you have the time, taking Route 1 along the coast is your best option. Not only will it show you some sweeping views of the Atlantic, but you can also make some stops at some iconic places along the way like Ogunquit , Old Orchard Beach , Kennebunkport , and Cape Elizabeth .

In addition, feel free to make a pit stop at the Holy Donut on your road trip if you need food. You can order a sea salt and chocolate potato doughnut once you’re there as well as some coffee.

By: Kelly of Girl with the Passport

Newburyport, MA (best road trips from Boston)

A trip to Newburyport is another great road trip you can do from Boston! The road trip will take about 45 minutes to complete and you can stop by Salem on the way there too.

In fact, according to Newburyport.com , there’s no shortage of things to do in this city. For example, the Clipper City Rail Trail is a 1.1 mile path that runs from the MBTA all the way to the Merrimack River Shoreline. You can run, walk, or bike on this path as you pass by some popular spots like the Graf Ice Skating Rink or the Cashman Park .

In addition, the Waterfront Park is another popular spot you can go to in Newburyport. It has ample green space that is used for sunbathing, relaxing, and hosting events.

Portsmouth, NH (best road trips from Boston)

Portsmouth, NH is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Market Square once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Portsmouth. For example, Prescott Park is a popular attraction that is located along the banks of the Piscataqua River. It has beautiful gardens of perennial flowers as well as a performance space and public docks.

In addition, the Prescott Park Arts Festival is also held at the park. This festival brings in many theater performances each summer as well as music.

Provincetown, MA (best road trips from Boston)

A trip to Provincetown is another great road trip you can take out of Boston! The road trip will take about two hours and a half to complete and you can do a lot of fun things while you’re there.

In fact, according to Vicky, you can take a sand dune tour at Provincetown’s Cape Cod National Seashore Park as well as climb to the top of the Pilgrim Monument for some amazing views.

In addition, there are many different art galleries you can visit in town. The gallery district is located in Provincetown’s East End section and it has Friday night art openings every week .

By: Vicky of Buddy The Traveling Monkey

Westerly, RI (best road trips from Boston)

A trip to Westerly, RI is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can check out Taylor Swift’s house once you’re there.

In fact, according to Business Insider , Taylor Swift bought the Rhode Island mansion for 17.75 million in 2013. She even paid for the entire mansion in CASH ! Imagine that. Taylor Swift is not only wealthy but she’s also not afraid to make a grand gesture.

Since then, the musician is continuing to put her home to good use by hosting A-list parties and events.

Lake Champlain, VT (best road trips from Boston)

A trip to Lake Champlain is another great road trip you can take out of Boston. The road trip will take about five hours to complete and you can visit the Waterfront Park once you’re there.

In fact, according to Inspirock, Lake Champlain also offers a range of different activities for outdoorsy fans as well as an exciting food scene. For example, the Burlington Bike Path is a great path near Lake Champlain where people can ride their bikes along the lake.

Lake Champlain also has a shop called Lake Champlain Chocolates where people can buy chocolate bars, truffles and caramels.

Plymouth, MA (best road trips from Boston)

A trip to Plymouth, MA is another great road trip you can take from Boston! The road trip will take about 40 minutes to complete and you can visit Plymouth Rock once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Plymouth. For example, the National Monument to the Forefathers is a popular tourist attraction that is located along Allerton St in Plymouth. The monument commemorates the founders of the Plymouth colony and it was dedicated in 1889.

In addition, try to see if you can do a Native Plymouth Tour once you’re there. This tour will help you see all that Plymouth has to offer with a Native American perspective.

Rockport, MA (best road trips from Boston)

Rockport, MA is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can snap pictures at Motif #1 once you’re there.

In fact, according to Addison Choate, Rockport has plenty of things to do that are under the radar. For example, just off the coast of Rockport you can visit Thatcher Island , an island known for its shipwrecks and for serving as a home for the mafia hitman turned informant, Joe Barboza .

He was a hitman for the Patriarca crime family during the 1960s and was a resident of the island back in 1967.

York, ME (best road trips from Boston)

A trip to York, ME is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can visit some other beautiful towns in Maine once you’re there.

In fact, according to Amanda, York has that classic coastal New England charm with its clapboard houses and stark white lighthouse. That stark white lighthouse in particular is called the Nubble Lighthouse .

Built in 1879, it is known to be haunted in York, ME by the ghost ship Isadore that wrecked nearby. If you’re interested in entering the lighthouse on your trip, go at your own risk. The lighthouse is not currently open to the public so it will be difficult.

By Amanda of Hey! East Coast USA

Block Island, RI (best road trips from Boston)

A trip to Block Island is another great road trip you can take out of Boston. The road trip will take about three hours to complete and you can go bike riding, kayaking and parasailing once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do on the island as well. For example, you can check out the views at the Mohegan Bluffs .

The Mohegan Bluffs are large clay cliffs that are located on the south shore of the island. They have views that are undoubtedly the best on the island, as you take in the scenery from the water and the beach.

Acadia National Park, ME (best road trips from Boston)

A trip to Acadia National Park is another great road trip you can take out of Boston! The road trip will take about five hours to complete and you can visit the Park Loop Road once you’re there.

In fact, according to James Ian, when you get to Bar Harbor, the gateway town to Acadia National Park, you can easily spend another few days there or even a week.

The area is known for its prime lobster fishing hub in Maine where you can order fresh seafood right from the water’s edge.

In addition, Acadia National Park is a hiker’s paradise. It has dozens of trails available through the woods that offer incredible views of the surrounding oceans and islands. These trails include but are not limited to the Beehive and the Precipice .

By: James Ian of Parks Collecting 

Charleston, RI (best road trips from Boston)

Charleston, RI is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the East Beach while you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Charleston as well. For example, Charleston has a top rated tourist attraction called the Fantastic Umbrella Factory .

It is known as a 19th century farmyard shoppers paradise in Charleston where visitors can shop at stores and admire local artwork. These stores include but are not limited to the General Store and the Frills. Local artwork can also be admired in the factory at the Henna Body Art.

Gilford, NH (best road trips from Boston)

Gilford, NH is another great road trip you can take from Boston! The road trip will take about an hour and a half to complete and you can visit the Gunstock Mountain Resort once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Gilford as well. For example, Gilford has a top rated tourist attraction called the Pepi Herrmann Crystal Gallery and Museum that features a wide range of crystal objects’d art like jewelry, Christmas ornaments, barware, home decor pieces, and stemware.

So, if this is of interest to you, feel free to stop by this attraction on your trip. Once you’re there you can also purchase and take home a small, inexpensive gift.

The Berkshires, MA *in general* (best road trips from Boston)

In the winter, a trip to the Berkshires is another great road trip you can take out of Boston! The trip should take about two hours to complete and you can go cross country skiing and snowshoeing once you’re there.

In fact, according to Karen, numerous hikes are also available through the Berkshire Hills. These hikes include but are not limited to Race Brook Falls, October Mountain Loop and the Bash Bish Falls.

The Bash Bish Falls in particular is where you can go to admire the highest waterfall in the state.

By: Karen of Outdoor Adventure Sampler

Gloucester, MA (best road trips from Boston)

A trip to Gloucester, MA is another great road trip you can take out of Boston. The road trip will take about 50 minutes to complete and you can visit the Good Harbor Beach once you’re there.

In fact, according to Addison Choate, Gloucester has plenty of things to do that are completely under the radar. For example, in Gloucester, you can visit the Hammond Castle Museum that’s located in the Magnolia area on the Atlantic coast.

The castle, which was constructed between 1926 and 1929, was also the home and laboratory of John Hays Hammond, Jr ., who was an inventor and pioneer in the study of remote control.

Lexington, MA (best road trips from Boston)

A trip to Lexington, MA is another great road trip you can take out of Boston. The road trip will take about 30 mins to complete and you can visit the Wilson Farm once you’re there.

In fact, according to Trip Savvy , there are a lot of other things you can do in Lexington as well. For example, in Lexington, you can visit the Lexington Battle Green where the American Revolution began. This spot also showcases the Revolutionary Monument which dates all the way back to 1799.

In addition, the Lexington Venue is also a great place to catch a movie. It’s a small town movie theater with two screens that shows a variety of feature and independent films.

Plum Island, MA (best road trips from Boston)

A trip to Plum Island is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit Bob Lobster once you’re there.

In fact, according to New England, there are a lot of other things you can do in Plum Island as well. For example, on the island, you can visit Plum Island Beach which is 42 miles away from Downtown Boston.

Therefore, if you’re planning on checking out this spot for the first time, I highly recommend going before sunset. This will give you the chance to see the beach as the sun sets so that you can take great pictures.

Kennebunkport, ME (best road trips from Boston)

A trip to Kennebunkport, Maine is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the Seashore Trolley Museum once you’re there.

In fact, according to Vacation Idea , there are a lot of other things you can do in Kennebunkport as well. For example, Kennebunkport has a top rated tourist attraction called the First Families Kennebunkport Museum.

It is operated by The Kennebunkport Historical Society and you can find it in an 1853 Greek Revival home on Main Street in a village.

Lenox, MA (best road trips from Boston)

A trip to Lenox, MA is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit The Mount, Edith Wharton’s Home once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do in Lenox as well. For example, Lenox has a top rated tourist attraction called the Berkshire Scenic Railway Museum .

It is an all-volunteer, non-profit organization dedicated to preserving the history of railroading and trolley lines in the Berkshire Hills of Western Massachusetts.

Ipswich, MA (best road trips from Boston)

A trip to Ipswich, MA, is another great road trip you can take out of Boston. The road trip will take about 40 minutes to complete and you can visit the Castle Hill on the Crane Estate once you’re there.

In fact, according to Travel Lens, there are a lot of other things you can do in Ipswich as well. For example, in Ipswich, you can meet some wolves at a top rated tourist attraction called the Wolf Hollow .

It is a non-profit wolf sanctuary and educational hub that’s dedicated to preserving the wolves in the wild with education and exposure.

Ogunquit, ME (best road trips from Boston)

A trip to Ogunquit, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 20 minutes to complete and you can visit Ogunquit Beach once you’re there.

In fact, according to Visit Maine, there are a lot of other things you can do in Ogunquit as well. For example, in Ogunquit, you can visit a top rated tourist attraction called Perkins Cove.

It is a small turn of the century fishing village that draws in great crowds every summer due to the boutique shops and fresh seafood.

Kittery, ME (best road trips from Boston)

A trip to Kittery, ME is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Kittery Historical and Naval Museum once you’re there.

In fact, according to The Crazy Tourist , there are a lot of other things you can do in Kittery as well. For example, in Kittery, you can visit a top rated tourist attraction called Badger’s Island.

Badger’s Island is an island that sits right in the middle of the Piscataqua River where several important boats were built many years ago. These boats include but are not limited to the Ranger, America, and Raleigh.

Westford, MA (best road trips from Boston)

A trip to Westford, MA is another great road trip you can take out of Boston. The road trip will take about 45 minutes to complete and you can visit The Butterfly Place once you’re there.

In fact, according to Boston Central , there are a lot of other things you can do in Westford as well. For example, in Westford, you can visit a top rated tourist attraction called Kimball Farm Mini Golf .

This attraction has two 18 hole adventure style miniature golf courses as well as a 6000 square foot bumper boat pond.

Fall River, MA (best road trips from Boston)

Fall River, MA is another great road trip you can do out of Boston! The road trip will take about an hour to complete and you can visit Battleship Cove once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, just down Water Street, you’ll find the City Gates Plaza, which is a tribute to the city’s sister city of Ponta Delgata.

In addition, this city also has the home of the famous axe murderer, Lizzie Borden . However, since the home is vacant, it is now being used as a Bed & Breakfast for tourists. So, if you like dark tourism and psychopathy, this spot is for you!

By: Kathryn of Staying Afloat Blog

Middlefield, MA (best road trips from Boston)

A trip to Middlefield, MA , is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit the Glendale Falls once you’re there.

In fact, according to Tripadvisor , there are a lot of other things you can do in Middlefield as well. For example, in Middlefield, you can check out Andrew’s gallery, DeVries Fine Art International Inc. , at the River Studio in the city.

The studio also has different series of Andrew’s sculptures that include but are not limited to dance, figurative, and abstract.

Sutton, MA (best road trips from Boston)

A trip to Sutton, MA is another great road trip you can do from Boston! The road trip will take about an hour to complete and you can hike the Purgatory Chasm once you’re there.

In fact, according to Sutton Mass, there are a lot of other things you can do in Sutton as well. For example, in Sutton, you can visit a top rated tourist attraction called Waters Farm .

In Waters Farm , you can enjoy horse drawn carriages in the summer, sleigh rides in the winter, and a wealth of other fun activities in between.

In fact, in my opinion, summer is the best time to visit since you’ll have the opportunity to participate in one of their festivals.

New Bedford, MA (best road trips from Boston)

A trip to New Bedford is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can follow the Self-Guided New Bedford Art Walk once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, in New Bedford, you can explore a beautiful collection of murals scattered across the city.

In addition, you can also immerse yourself in New Bedford’s beautiful architecture by walking along the city’s cobblestone streets.

Cape Cod, MA *in general* (best road trips from Boston)

A trip to Cape Cod is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can stop by the Cape Cod National Seashore once you’re there.

In fact, according to the U.S. News and World Report , there are a lot of other things you can do in Cape Cod as well. For example, in Cape Cod, you can visit a top rated tourist attraction called Cape Cod Rail Trail.

Previously known as the Old Colony Railroad corridor, the Cape Cod Rail Trail is considered to be one of the best biking trails in New England.

Agawam, MA (best road trips from Boston)

A trip to Agawam, MA is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can visit Six Flags New England once you’re there.

In fact, according to Theme Parks and Entertainment , Six Flags New England is known for having some of the best roller coasters in the world. These roller coasters include but are not limited to The Great Chase, Catwoman’s Whip, and Goliath.

Superman The Ride is also the best ranked roller coaster in the park while The Great Chase is the worst.

Overall, I really hope you enjoyed this post on the 30 best road trips you can take from Boston! Please let me know in the comments down below which road trip destination you would like to visit the most! I would love to hear from you. 🙂 P.S. If you’re looking for some things to do in NYC, check out this post on the 101 things you can do alone while you’re there.

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Reader interactions.

April 7, 2022 at 16:36

Great road trips, I would love to be able to get across to take one or two soon…..

April 7, 2022 at 14:29

Acadia National Park would be my top weekend trip, hiking plus eating the best lobsters is hard to beat!

April 7, 2022 at 15:10

April 6, 2022 at 17:50

So many great ideas here, and such beautiful scenery. I would definitely look at basing myself in Boston and doing day trips

April 6, 2022 at 20:07

Thank you so much Elyse!

April 6, 2022 at 17:02

this native Bostonian approves of this list! Great recommendations and some of my favs spots (Gloucester, Newport)

April 6, 2022 at 17:04

Thank you Jennifer!!! 💓

April 6, 2022 at 16:37

OMG, I pretty much want to do ALL of these! I’m going to need a little time in Boston!

I KNOW RIGHT

April 6, 2022 at 16:28

This is such a great post with so many awesome recommendations! We traveled to Newport, Portland, Portsmouth, and Plymouth during our time in Boston this summer and are dying to go back to explore some more of these. Thanks for sharing!

April 6, 2022 at 16:31

You’re so welcome Brittany! I’m glad you enjoyed it.

April 4, 2022 at 14:07

So many fantastic places to go. How fun. Thanks for sharing.

April 4, 2022 at 17:46

You’re so welcome!

April 3, 2022 at 07:56

Oh so many beautiful places that you can visit from Boston! great inspiration for future!

April 3, 2022 at 10:01

Thanks Lasma!!

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30 Best Road Trips from Boston: Destinations To Explore

Boston is an incredible place, one that I lived in for several years. But every so often, I needed to get out of the city and make a day trip somewhere nearby. Boston is central to a number of places, and here are my suggestions for the best road trips from Boston. I sort them by distance, so you can choose the trips that best fit your schedule.

Where Can I Drive To From Boston?

If you have a vehicle, I would absolutely recommend leaving Boston, but if you’re going to stay in the city, read my article about Driving In Boston or Best Food in Boston . Within 6 hours of Boston, you can hit the Quebec Province of Canada , Maine , New Hampshire , Vermont , Connecticut, Rhode Island, New York, New Jersey, and Pennsylvania.

Is driving in Boston hard? Find out here !

What cities are within driving distance from Boston?

We defined driving distance as within 6 hours. That gives you time to make the drive there, explore and make it back in less than a day. So, here is our list of 30 best road trips within driving distance of Boston.

Where can you drive in 6 hours from Boston?

Lancaster, pennsylvania (6 hours: 2 minutes).

In a world in which malls are becoming less common, Park City Center Mall is the largest mall in South Central Pennsylvania with over 150 stores. Also in town is the Lancaster Central Market, the oldest continuously operated farmers market in the US. Which sells Amish goods not commonly found anywhere else. Finally, for watch enthusiasts, the National Watch & Clock Museum has the largest collection of closes and watches in North America.

Quebec City, Quebec (5 Hours: 58 Minutes)

Located on the north bank of the St Lawrence River, this Canadian city has lots of European designs to it. Areas such as Vieux-Quebec, Chateau Frontenac, and Notre-Dame de Quebec Cathedral have beautiful architecture. Just note that the primary language is French, you’ll still find some English speakers in the more touristy areas.

Atlantic City, New Jersey (5 Hours: 26 Minutes)

Known for its casinos, boardwalks and beaches, this is a popular tourist destination. Additionally the 9 casinos in one city is one of the ways it resembles a smaller version of Las Vegas. They also have 3 large shopping centers, 2 convention centers, and numerous beaches. Lastly, for fans of Monopoly, all of the spaces are named after locations in and around Atlantic City.

Philadelphia, Pennsylvania (5 Hours: 2 Minutes)

The largest city in Pennsylvania, and one of the leading cities in higher education in our country with 18 universities and colleges. Philadelphia was also our first US Capital which means there is lots of history in it. Additionally, the most famous monument being the Liberty Bell. is found here. The city has the most outdoor sculptures and murals of any US city.

Syracuse, New York (4 Hours: 31 Minutes)

Incorporated in 1825, Syracuse has grown substantially as a major hub and education center of New York with Syracuse University and two SUNY universities. With a huge arts focus, it is home of the Syracuse Jazz Festival and Polish Festival. It also has orchestras, opera companies, several theatres, and 5 museums.

Bar Harbor, Maine (4 Hours: 27 Minutes)

Located on Mount Desert Island and is home to Acadia National Park. Acadia National Park is a beautiful coastal park with hiking trails, boating, and camping. Home of Jackson Laboratory and MDI Biological Laboratories with a focus on marine life research. With over 2 dozen hotels and nearly 200 cruises arriving every year, it’s evident that this is a tourists favorite destination.

Long Island, New York (4 Hours: 12 Minutes)

The longest and largest island in the contiguous United States, Long Island is the most populated island anywhere in the US. With 8 big sports stadiums, golf courses, horse racing, and the national tennis center. It is truly a great place for sports lovers. In addition to theatres, music venues, and other entertainment venues, it’s definitely got the big city feel.

Road Trip Destinations around 3 hours from Boston

New york city, new york (3 hours: 12 minutes).

What’s better than a road trip to the Big Apple? With 5 boroughs, hundreds of diverse neighborhoods, skyscrapers, and Broadway, you could spend weeks in New York without getting bored. It is the city that never sleeps for a reason. Just note, that traffic in and near New York City can be a nightmare.

Pro Tip : if the traffic and parking in NYC is stressful, consider taking a train! It takes about as long as driving but you don’t have to worry about a car.

Danbury, Connecticut (3 Hours)

Nicknamed the “Hat City” due to its ties to the hat industry. Danbury is ranked as the most diverse city in New England by WalletHub. With lots of parks, hiking trails, and a railroad museum, there are some fun things to see and do. If you like old buildings, they have 12 on the National Registry of Historic Places.

Schenectady, New York (2 Hour: 59 Minutes)

Settled in 1661, this small (10.98 square mile) city still has lots to offer. With a golf course ranked as “Best places to play” by Golf Digest. This small city also boasts some beautiful architecture, as well as the first planned residential neighborhood and college campus. The Rivers Casino and Resort is worth visiting as well.

Bridgeport, Connecticut (2 Hours: 54 Minutes)

The largest city in Connecticut, and a major shipping port, this city got its start in 1821. Infamous showman P.T. Barnum was a resident and housed his circus in Bridgeport in the winters. Home of the world’s first Subway restaurant and where the electric plug outlet was invented. Additionally with 1,300 acres of green space in 35 community parks, the city has earned the nickname “Park City.”

North Conway, New Hampshire (2 Hours: 52 Minutes)

A small little town in New Hampshire, North Conway was originally chartered in 1765, nestled in the White Mountains. A perfect place for those who love outdoor activities. The Echo Lake State Park provides boating, swimming, and rock climbing. In the winter, Cranmore Mountian Resort provides 200 acres and 54 trails of skiing.

Trumbull, Connecticut (2 Hours: 52 Minutes)

With 20 local parks and one big state park, Trumbull has lots of green space to enjoy. In addition to the parks, they have four sites on the National Registry of Historical Places. If you happen to be around in October 2097, they buried a time capsule to be opened then.

Martha’s Vineyard, Massachusetts (2 Hours: 50 Minutes)

About a third of the travel to Martha’s Vineyard includes the ferry ride. However you can take your car over, so it’ll still count as a road trip with beautiful on-ocean views. Technically there are 6 towns on the island, but in a lot of ways they work together as one. With a long list of famous individuals having homes or regularly visiting the island, including 3 former presidents, it has been nicknamed “Hollywood East.”

Killington, Vermont (2 Hours: 47 Minutes)

Chartered in 1761, and then renamed in 1999, Killington is home to the Killington Ski Report. The largest ski area in the Eastern US. Nicknamed the “Beast of the East,” the resort has 155 trails, 21 lifts, and just over 1,500 acres to ski. With the town having less than 2,000 permanent residents, skiing is the only reason to trek out to Killington.

Killington, Vermont is also a great place to visit in the fall for all the incredible fall foliage . Enjoy driving around Vermont to see everything the state has to offer.

Albany, New York (2 Hours: 43 Minutes)

The capital of the state of New York since 1797 when the US was formed. It is also the longest continuously charted city in the United States, starting in 1686. As a major city, it has all of the attractions of a city, without all of the people. 70% of their permanent population comes from the 7 colleges and universities within Albany, including the nationally recognized SUNY Albany.

Road Trip Destinations within 2 hours from Boston?

Newport, rhode island (2 hours: 4 minutes).

Known as the Sailing Capital of the world, Newport has several big claims to fame in the sports arena. The first U.S. National Tennis Championships, the second is the home of the National Sailing Hall of Fame and finally, the International Tennis Hall of Fame. They also have a close relationship with the navy, housing the Naval War College and Naval Undersea Warfare Center since 1861.

Berkshire, Massachusetts (2 Hours: 2 Minutes)

In Massachusetts, when you want to get away to somewhere quiet and relaxing, it’s often a day trip to the Berkshires. With lots of history, good food, shopping, and lots of outside activities, it’s a great escape from the city. Additionally it has so many cute hotels and AirBnBs for a relaxing getaway.

Enjoy some more great small towns in Massachusetts here !

Kennebunkport, Maine (1 Hour: 45 Minutes)

Originally settled in 1653 as part of Massachusetts, Kennebunkport is another beautiful coastal town. Along with the numerous beachfront hotels, it is also the summer home of former presidents George H. W. Bush and George W. Bush. With lots of summer activities and miles of beaches, it’s a popular tourist destination.

Portland, Maine (1 Hour: 41 Minutes)

The largest city in Maine, with ocean views and vibrant nightlife. Old Port hosts dozens of restaurants and bars all within walking distance of each other, it’s known as a destination for foodies. Additionally there’s two big universities, a baseball stadium, a basketball court, an observatory, and a large few large performance venues. They have something for everybody.

Providence, Rhode Island (1 Hour: 41 Minutes)

The capital and largest city in Rhode Island was settled in 1636. It was also one of the original thirteen colonies. Now it’s a growing city with eight hospitals, eight institutions of higher learning, several museums, the oldest baptist church in America, and a zoo. Of course, you can’t forget the roadside attraction, Nibbles Woodaway , the world’s largest artificial bug atop the Big Blue Solutions building.

Ogunquit, Maine (1 Hour: 31 Minutes)

Another oceanside town settled in 1641, it served as the first sawmill in the United States and grew into a shipbuilding town. Famous for fishing, it currently has a Museum of American Art, a playhouse, and a couple of beaches. With a population of less than 2,000 year-round residents, it’s one of the least populated towns on our list.

Road Trip Destinations about an hour from Boston?

Cape cod, massachusetts (1 hour: 15 minutes).

A peninsula extending into the Atlantic Ocean, it includes 15 unique towns. It’s broken into Upper Cape, Lower Cape, and Mid-Cape. If you like seafood or lighthouses (there are 19 of them), this is a beautiful drive with friendly locals.

Wachusetts, Massachusetts (1 Hour: 5 Minutes)

Another great ski destination, and one of the ones listed in our Best Skiing in New England article . With 100% snowmaking capacity and night skiing on most trails, it’s a great local mountain. In addition to the ski resort, there is a Great Wolf Lodge located nearby with indoor pools and water parks.

Want more great ideas for ski resorts in New England? See our article about the Best Skiing in New England .

Hampton, New Hampshire (1 Hour: 3 Minutes)

Heading north from Boston, you’ll the little town of Hampton, NH. While over 2,000 of the homes in town are for “seasonal or recreational use,” meaning that they have lots of rental housing if you wanted to spend the night. They are most popular with summer tourists, with a beach, a state park, and a music venue.

Rockport, Massachusetts (55 Minutes)

One of our favorite places to visit and walk around downtown. Founded in 1840, it’s right on the coast and has beautiful views of the ocean. With a very walkable downtown (and even colored routes marked out on the sidewalk), and lots of cute local stores, you could spend hours and not run out of things to see.

Worcester, Massachusetts (51 Minutes)

The second most populated city in New England, Worcester also has the second largest art museum in New England and the oldest pipe band in the US. It’s also home to Worcester Polytechnic Institute, Worcester State University, and College of the Holy Cross, one of the oldest Catholic colleges in America, and 6 other universities. Additionally it has all the activities of a big city without the crowded streets.

Plymouth, Massachusetts (50 Minutes)

Home of Plymouth Rock , where the pilgrims landed in 1620, making it one of the oldest colonies in the United States. Also the home of America’s first thanksgiving feast, this is a town that embraces its history at the start of our country.

Salem, Massachusetts (40 Minutes)

First settled in 1626 by English Colonists, Salem was a major seaport for the North Shore area. Most famously known for the Salem Witch Trials, they take Halloween and all things witches very seriously. They seem to celebrate Halloween all year long , with year-round haunted house tours, psychic conventions, and lots of ghost stories.

Foxborough, Massachusetts (39 Minutes)

Once home to the world’s largest straw hat factory, it’s now known most commonly as the location of the Gillette Stadium. Gillette Stadium is home to the New England Patriots Football team, but is also a FIFA World Cup location in 2026. Outside of the stadium is primarily support businesses, such as the restaurants and shops in The Patriot Place Shopping Plaza.

Enjoy some fun Boston-specific events like Boston First Night or Boston Marathon .

How Far Is It From Boston To The Maine Border?

From downtown Boston to the Maine border is just about an hour, making it a very easy day trip. Maine has some beautiful ocean views and island escapes. If you wanted to continue your drive through Maine, see our Maine Category for some great ideas. If you’re trying to decide between visiting Maine or New Hampshire though, there are definitely pros and cons to both.

How Far Is It From Boston To The New York Border?

From downtown Boston to the New York border is about 3.5 hours, or 183 miles, making it a very easy day trip. New York, Long Island, and New Jersey are all great locations for all of the activities of the big cities.

13+ Unforgettable Road Trips from Boston to Take This Year

Boston, a charming Northeast city, is best known for its role in American history. While there are plenty of things to do in Boston on its own , there are also so many surrounding cities and parks that are only a quick road trip from Boston that are also worth exploring!

Having grown up in California, I was not used to the accessibility of other states until living on the east coast! It’s as easy as hopping in your car, and you could be in another state or city near Boston exploring a state park, a beach, or a wine region!

With the help of my fellow travel bloggers, we have crafted a list of the best road trips from Boston that I encourage YOU to take this year!

So, let’s get into it!

Planning a trip in 2024? Check out some of my favorite resources!

For flights:.

Expedia makes booking flights extremely easy. I found that they always have the cheapest flights, and have not had any issues with their customer service.

For HOTELS:

I use Booking or all of my hotel reservations. The platform is extremely easy to use, and you always get the best rate because of their price guarantee.

For Activities:

I love booking activities before a trip with Get Your Guide! I have had a good experience with all of the activities I booked, and found they have the most affordable prices.

Disclaimer: This post may contain affiliate links. If you click on a link, we may earn a small commission if you purchase through these links at no additional cost to you.

Table of Contents

Map of the Road Trips from Boston Destinations

Here is a map showing all of the destinations that this list of the best road trips from Boston includes!

The Best Road Trips from Boston

On this list, you will find some road trips that will take you under an hour, and some that might even need to be broken up into multiple days! We’ve included the road trip length and distance to allow you to better plan your journey.

1. Boston to Mystic, CT

• Road trip destination: Mystic, CT
• Road trip length: 2 hours
• Road trip distance: ~100 miles
• Route taken: I-95 S
• Best time for road trip: June to August and during the fall foliage season (September/October)

Recommended by Kitty from  Kittymeetsworld

Driving to Mystic, Connecticut makes for an excellent road trip from Boston. The drive itself will take around two hours (and in fall offers a chance to admire autumn colors).

If you want to break up your journey, you could stop in Providence, RI, to check out the beautiful campus of Brown University and the downtown area. Closer to Mystic, Saltwater Farm Vineyard on the Connecticut Wine Trail would also make for a fun stop.

But, the highlight of this road trip is the destination . Mystic is the prototype of a traditional coastal New England town. With its clapboard houses, white church, tree-lined streets, and quaint stores, the historic downtown of Mystic is ideal for a stroll. If you time it right, you may even see the bridge being raised to let sailboats pass through!

Don’t miss out on a visit to Mystic Pizza, made famous by the 1988 film with Julia Roberts. If you would rather enjoy seafood in a casual atmosphere, nearby Noank has two popular lobster eateries. Watch out for seagulls though if sitting outside – they will steal your food if you are not careful!

Aside of the charming village that seems to be straight out of a Norman Rockwell painting, Mystic boasts another major attraction: Mystic Seaport. Seaport Village recreates life in a whale fishing village in the 1880s and is a must-see on your road trip.

In the summer and on weekends, docents in period clothing show traditional craft, fishing, and farming methods. In addition, you can explore historic boats and even take a ride on a steamboat.

2. Boston to the Berkshires, MA

• Road trip destination: The Berkshires, MA
• Road trip distance: 125 miles
• Route taken: I-90 W
• Best time for road trip: Summer

Recommended by Karen of Outdoor Adventure Sampler

The Berkshires in Western Massachusetts are an ideal road trip from Boston. Located a mere two hour drive from Boston, the vacation paradise of the Berkshire mountains is a spectacular place to explore. Take the Mass Turnpike for 125 miles to the western part of the state to access the many small towns.

Visitors are drawn to the outdoor beauty of the Berkshires in all seasons. Outstanding fall foliage is a showcase for travelers from all over the world. In the winter, the Berkshires become a snowy wonderland.  Cross country, snowshoeing, and downhill skiing areas  can be found throughout the Berkshires.

However, summer may be the most popular season to visit the Berkshires. Charming villages with boutique shops and farm to table restaurants abound. 

Besides outdoor activities, the Berkshires area is home to the Norman Rockwell Museum, the Clark Museum, and the innovative Massachusetts Museum of Contemporary Art (MassMOCA). The Berkshires also boasts the open air music venue Tanglewood. It has an immaculate lawn for spreading out a picnic while watching world-class concerts. The summer home of the Boston Symphony Orchestra is also at Tanglewood.

I enjoy spending a few days in the Berkshires to see some of the natural beauty such as Bash Bish Falls. It’s also easy to immerse in the culture and spend a few hours exploring the museums and historic towns. End the day with a stay in one of the classic New England inns with stone fireplaces and historic touches.

3. Boston to Chatham, MA

• Road trip destination: Chatham
• Road trip length: 1.5 hours with no traffic
• Road trip distance: 87 miles
• Route taken: take I-93 South out of Boston and then merge onto Route 3 South
• Best time to take road trip: Summer or Fall

Recommended by Fab 5 Family Travel

Chatham is one of the most beautiful destinations on the Cape, and recently was able to take this road trip with my husband on summer vacation! We flew into Boston and left directly from the airport. We arrived mid-morning, so didn’t experience much traffic but keep in mind the traffic worsens on Fridays and on the weekends as people flee the city for the Cape beaches.

We loved our stay at the Greyfinch Inn and our time exploring Chatham. Some of the best things we did were stroll through the charming downtown, see the seals at the Chatham Fish Pier, eat fresh seafood, and visit the iconic lighthouse.

Chatham’s beaches are gorgeous and a great way to unwind. If visiting in the summer, make sure to secure a parking pass for the popular beaches and catch a baseball game in the Cape Cod Summer League. 

While in Chatham, you must go to the Cape Cod National Seashore that stretches throughout the Cape. It was a highlight of our trip. If you love history, learn about the region’s history at Chatham Marconi Maritime Center or the Atwood House Chatham Historical Society.

4. Boston to Martha’s Vineyard, MA

• Road trip destination: Martha’s Vineyard
• Road trip length: 1.5 hours to Woods Hole then a 45 minute ferry ride to the island
• Road trip distance: 70-80 miles
• Route taken: I-93 South from Boston, merging onto MA-3 South, and then continuing onto US-44 West. Then I-495 South to MA-25 East. Follow signs to Cape Cod/The Islands.
• Best time to take road trip: Mid-week in early June for lighter crowds and pleasant weather. Avoid peak summer weekends if you’re not a fan of traffic. 

Recommended by Maria from Martha’s Vineyard Travel Tips

Martha’s Vineyard is the perfect destination for a road trip from Boston. If you time it just right, you can be sitting on the beach, basking in the sun less than 3 hours after leaving home. 

Some of my favorite things to do are to take a stroll around the colorful gingerbread cottages in Oak Bluffs or visit Edgartown Lighthouse. If you really want to get away from it all, I recommend hopping on the Chappy ferry and visiting the secluded, pristine beaches of  Chappaquiddick .

When you arrive on Martha’s Vineyard, you’ll find a charming island full of fascinating history, quaint shops, boutique inns and incredible local seafood restaurants. 

I’ve done this road trip several times and I recommend hitting the road early. Even though the journey is less than 80 miles, if you hit that Cape Cod traffic on a summer weekend, your driving time can double! It’s also essential to make a car reservation well in advance of your trip.

5. Boston to Salem, MA

• Road trip destination: Salem, Massachusetts
• Road trip length: 35 minutes
• Road trip distance: 25 miles
• Route taken: I-95, I-93, MA 128 N at Exit 40
• Best time to take road trip: Summer for great weather or Fall for Halloween festivities

Recommended by Mackenzie Jervis, A Wandering Scribbler

Heading out on a road trip through Massachusetts to Salem, MA, is not just a journey through miles but a voyage through time, history, and mystique. Salem, with its enigmatic past as the site of the infamous witch trials of 1692, has an intriguing blend of the eerie and the enchanting.

The road trip from Boston to Salem is only about 25 miles, offering a scenic drive through the charming New England landscape. Along the way, travelers can pause to explore historic landmarks such as Marblehead, known for its colonial architecture and maritime heritage.

In Salem, the cobblestone streets feel like stepping back in time. Attractions like the Salem Witch Museum and the House of the Seven Gables, where Nathaniel Hawthorne found inspiration for his novel of the same name, are great places to explore. While Salem is worth a visit any time of the year, the city truly comes alive in the fall. Salem’s Halloween festivities , held each October, are like a giant party throughout the town for those who love witches, spooky activities, and the history of the witch trials.

Salem also has a lively arts scene, with galleries, boutiques, and artisan shops lining its streets, offering a modern contrast to its historical significance. Salem’s food scene offers fresh seafood and locally sourced fare, while its waterfront promenade provides a serene backdrop for relaxation. Whether drawn by history, culture, or simply the allure of the unknown, a road trip to Salem from Boston promises an unforgettable adventure steeped in mystique and charm.

6. Boston to Ocean City, MD

• Road trip destination: Ocean  City, Maryland
• Road trip length: 7 hours
• Road trip distance: 450 miles
• Route taken: I-84 to CT-91 to CT-15 to Hutchinson River Pkwy to Cross County Pkwy to Henry Hudson Pkwy to I-95 to NJ Turnpike to 1-295 to 1-95 to US-13 to US-113 to US-50
• Best time to take road trip: Summer

Recommended by Denise from Chef Denise

A road trip to Maryland is a perfect way to spend a summer weekend! I’ve done this road trip from Boston to Ocean City many times, and it can easily be done in a day. However, I prefer to make some stops along the way as this route goes through two of America’s most amazing cities: New York City and Philadelphia. It’s even more worth it if you can spend a night in each. 

You can drive to Manhattan in about 4 hours from Boston. I like to leave early so I can have lunch in the city and take a long walk down 5th avenue and through central park. Then I have an amazing dinner, preferably where the view of the Brooklyn Bridge rivals the food.

From NYC to Philadelphia, it’s less than two hours. So I load up on a big breakfast at Veselka in the East Village before hitting the road. As a big foodie, in Philadelphia I’m happy wondering around Reading Market all day and landing where my taste bud take me. With a good dose of historical sights mixed in, of course. 

Then, it’s just 2.5 hours to Ocean City. Summer is the best time to visit Ocean City because as the name implies, this is a resort town that comes alive from Memorial Day through Labor Day. With a seven mile boardwalk, a warm Atlantic Ocean, and lots of water activities, the beach is where you’ll want to be. It’s also where you’ll find the  best crab restaurants in Ocean City —the real reason to visit in summer—crab season!

7. Boston to Acadia National Park, ME

• Road trip destination: Acadia National Park
• Road trip length: 5 – 7 hours
• Road trip distance: 300 miles
• Route taken: Highway 1 and 1A along the coast
• Best time to take road trip: Fall. The leaves and changing and the oysters are delicious

Recommended by Melody Fanslau from  The Winding Road Tripper  blog

A road trip to Acadia National Park is full of quaint towns and beaches, so it will be jam-packed with options for you to create your own trip depending on the amount of time you have.

One of the best parts about this road trip is it takes you along quiet highways along the coast (Highway 1 and 1A) and avoids Interstate 95.  

The best stops along this route include Salem, MA, Portsmouth, NH, Portland, ME, Camden, ME, and Bar Harbor/Acadia National Park, ME.

Salem hooked me with its eerie past and quirky museums. It was like walking through history with a spooky twist. Then, Portsmouth was a breath of fresh air—historic yet lively. Cafes, shops, and that old-world charm made it the perfect pit stop.

Maine was a showstopper with its scenic beaches and quaint towns. Portland was a blend of city cool and seaside charm. I had some of my favorite cocktails at Blyth & Burrows. The Portland Head Light was postcard-perfect, and wandering the Old Port was a day well spent.

Maine has many great coastal towns, but Camden was one of my favorites. You can spend time hiking in Camden Hills State Park or take a sunset sail. 

As for Acadia National Park, it was the grand finale. From the stunning views on Cadillac Mountain to the serene beauty of Jordan Pond, it was nature at its best.

This road trip was more than just a drive; it was a collection of awesome stops, breathtaking views, and delicious eats. Each stop had its unique flair, making the journey unforgettable.

8. Boston to Portsmouth, NH

• Road trip destination: Portsmouth, NH
• Road trip length: 1.5 to 2 hours with traffic
• Road trip distance: 62 miles
• Route taken: Interstate 95
• Best time to take road trip: September to November, during fall foliage season

Recommended by Stacy from Explore Baja California

Portsmouth is a historic city in that boasts a well-preserved downtown area with cobblestone streets, brick sidewalks, and elegant colonial architecture that is perfect for a weekend getaway from Boston.

If you don’t have a car, there are also bus services available between Boston and Portsmouth. Companies like Greyhound, C&J Bus Lines, and Concord Coach Lines operate several buses per day between these two cities. 

June to August is the peak season in Portsmouth. The weather is warm, and there are numerous outdoor activities and you can enjoy outdoor festivals, concerts, and dining. The downside is that it can get crowded, and accommodation prices may be higher during this time. 

September to November is fall foliage season in New England, including Portsmouth, which is renowned for its stunning colors. I visited Portsmouth in September and had a great time, as it was still sunny and pleasant to be around.  

The weather is generally pleasant throughout September and the first half of October, and there are still plenty of outdoor activities to enjoy, such as hiking and leaf-peeping. And, it is the visit fall-themed events and enjoy seasonal treats like apple cider and pumpkin-flavored treats at local farms and stores!

9. Boston to White Mountains, NH

• Road trip destination: White Mountains, New Hampshire
• Road trip length: Approximately 2.5 to 3 hours one way
• Road trip distance:  About 160 miles one way, depending on the specific destination within the White Mountains and the starting point in Boston.
• Route taken: I-93 North from Boston to the White Mountains. This route provides a direct path to many of the region’s attractions and scenic areas.
• Best time to take road trip: Fall

Recommended by Sophie from Delightful Travel Notes blog

A road trip from Boston to the White Mountains promises a mix of natural beauty, adventure, relaxation, and family fun. As you approach the White Mountains, the view transforms into a breathtaking vista with rugged mountain peaks, dense forests, and crystal-clear streams.

The best time to take this road trip is in the fall. Fall is a highly popular time to visit due to the spectacular fall foliage. The weather is also pleasant for hiking and outdoor activities.

Summer months are also perfect for those interested in hiking, camping, and other outdoor activities. The weather is warm, and all attractions and trails are open, including mountain coasters and water parks.

The area has a wide range of activities year-round but it is extremely beautiful in the fall. The forests become a vivid palette of reds, oranges, yellows, and golds. When visiting this region, we like to stay in North Conway, which is very convenient to access attractions and scenic drives, especially the famous Kancamagus Highway.

Due to its popularity, it is important to plan ahead if you want to see fall colors in the White Mountains. Accommodations can fill up quickly, and some areas may experience heavy traffic, especially on weekends.

10. Boston to Montauk, NY

• Road trip destination: Montauk, NY
• Road trip length: Around 5 hours
• Road trip distance: 202 miles
• Route taken: I-90 West, I-395 South, RT-32, then take Cross Sound Ferry
• Best time to take a road trip: Late spring is the best time to visit as you will get to experience warm temperatures but fewer crowds. 

Recommended by Samantha Oppenheimer of Find Love and Travel

I couldn’t recommend a better road trip from Boston than a trip to Montauk. You will find this wonderful beach town located at the end of the peninsula of Long Island, New York. Montauk is the perfect location for a spring or summer getaway! 

This is unlike any other locations that you’re probably familiar with in New York as it has a much more serene atmosphere, instead of the bustling streets and city lights. Plus, during your drive from Boston, you’ll get to experience some pretty incredible scenery, too.

The road trip is worth taking because there are so many great attractions to visit while there. Hiking and biking are both some of the best things to do in Long Island, and are very popular since there are six state parks to choose from. The Montauk Lighthouse is a great family-friendly activity. Then, after a day of driving and exploring, you can settle down on one of the beaches to enjoy an incredible sunset. Gin Beach is my favorite! 

11. Boston to New York City, NY

• Road trip destination: New York City
• Road trip length: Approximately 4 hours (with no stops)
• Road trip distance: 220 miles
• Route taken: There are multiple routes via I-90, I-95, or I-84 (each route offers different options for stops along the way)
• Best time to take the road trip: Summer or fall would be ideal

Recommended by Rebecca from Veggies Abroad

A road trip from Boston to NYC offers a scenic journey through picturesque small towns, ending with the Big Apple! If this is your first East Coast road trip adventure, I suggest taking the route via I-95 so you can enjoy a mix of scenery.

This route is especially great in the summer as you will have beautiful weather and longer days, but it’s also beautiful in the fall with the colorful foliage. I would avoid it in the winter, as the East Coast can be pummeled with snow and brutal winter weather. 

As you head to NYC via I-95, consider making two stops, first in Providence, Rhode Island, and second in the quaint town of Mystic, Connecticut.

In Providence, try to plan your trip around one of their unique WaterFire events! Generally, from late spring through fall, the city lights bonfires along the river, and there are activities and live music.

Mystic, Connecticut, is a charming small town known for its maritime museums, but it’s also the setting for one of Julia Roberts’s early movies, Mystic Pizza! The pizzeria that inspired the movie is still in town and serving up slices!

Once you get to NYC, you’re going to want to ditch the car — heads up, parking fees are astronomical! Just about every hotel offers parking, but be sure to check the prices before you book. NYC is one of the best cities in the US to explore. It’s home to endless entertainment, activities, and just about every type of food you can imagine, from greasy pizza to  fancy plant-based eateries.

12. Boston to Newport, RI

• Road trip destination: Newport, Rhode Island
• Road trip length: 3 hours
• Road trip distance: 156 miles
• Route taken: I-93 S to MA-24 S and RI-24 S to RI-114 S/W 
• Best time to take road trip: late Spring to early summer or late summer to early fall

Recommended by Jenifer of The Evolista

One of the best road trips from Boston is to the mansions of Newport, Rhode Island. The journey is only a few hours, and a step back in time to the Gilded Age. 

The Breakers, built as the summer residence for Cornelius Vanderbilt II, is the most notable of the Newport mansions. Step into 19th-century opulence and see the architectural grandeur of the Breakers. Then take the Cliff Walk, a scenic path with views of the Atlantic Ocean, to see Rosecliff, where many TV shows and movies have been filmed, and the Chinese Tea House at Marble House.

Fort Adams State Park is the largest fortification on the East Coast with cool tunnels and panoramic vistas of Newport Harbor. If you’re lucky, you may be able to see a concert or sailing race while there. 

Check out the shops on historic Thames Street and walk to Bannister’s Wharf for a meal at Clarke Cooke House Restaurant. On one of your days, take a sailing cruise or a ferry for a  day trip to Block Island . Once you arrive, rent a bike to tour Block Island’s beaches, lighthouses, and the Great Salt Pond. Have lunch at the Oar and order a mudslide before heading back to Newport. 

On the return trip to Boston, stop in Providence to visit the RISD Design Museum, Roger Williams Park and College Hill. This road trip is best done in 3-4 days and lets you experience a variety of New England bucket list activities.

13. Boston to Providence, RI

• Road trip destination: Providence, RI
• Road trip length: 1 hour
• Road trip distance: 51 miles
• Route taken: via I-93 S and I-95 S
• Best time to take road trip: October

Recommended by Tanya Taylor,  Travels & Treasures

Whenever I take a trip out of town I try to make the most of it and visit another city that is nearby.  So when I booked a girl’s trip to Boston, Massachusetts I thought it would be great to see Providence, Rhode Island. 

I booked a stay for two nights.  On the way, we enjoyed seeing the change of the colorful leaves during the Fall season.

The town was easy to get to and we only had to be on the road for 1 hour.  We settled into our hotel for the evening and awoke refreshed and ready to explore.

First, we went to Brown University and walked around the campus.  It was particularly interesting to learn that it was one of nine colonial colleges founded before the American Revolution. The downtown area was rather small but quaint.  The area is artsy with lots of boutique stores and unique finds.

My favorite experience was exploring Waterplace Park and Federal Hill.   Waterplace Park is situated along the Woonasquatucket River with pedestrian paths along the riverwalk.  It’s a great spot for a morning stroll or to grab bites and shop when the outdoor market is open.

Federal Hill is a happening neighborhood where locals hang out as a community.  We stopped at Costantino’s Venda Bar & Ristorante, an old Italian restaurant, and sat outdoors near a fountain while listening to live entertainment.  We were also fortunate to catch the start of the Rhode Island Seafood Festival in India Point Park. The stay was short, but the road trip inspired me to have more adventures.

14. Boston to Burlington, VT

• Road trip destination: Burlington, Vermont
• Road trip length: 5 hours and 40 minutes
• Road trip distance: 276 miles
• Route taken: MA-2, VT-9 W, Vt Route 7, I-91 (briefly)
• Best time to take road trip: May-July, September-October

Recommended by Amy Hartle of New England With Love

Vermont is a destination that calls to so many. Green as can be in the summer and vibrant with foliage in the fall, it’s my personal favorite state in New England. If you’re visiting Boston, it’s not a hop skip and a jump up to Vermont, but heading up and taking a  road trip through Vermont  is 100% worth it.

This trip can be done in one day if you’re feeling up to it, but I recommend a slower pace. If you take Route 2 straight out of Boston, you’ll pass Lexington and Concord: a must stop for history and literary buffs. Once you’re in Vermont, consider stopping overnight in Brattleboro, a fun hip town that’s a bit off the radar. 

After departing Brattleboro, you’ll cross over the mountains along Route 9, a winding road that is especially beautiful in the autumn. Don’t miss the scenic overlook in Marlboro at Hogback Mountain, which offers a “100-mile view.” Gorgeous. 

If Brattleboro doesn’t appeal, Bennington also has a lot of cool things to do, from art to coffee culture to its iconic Bennington Battle Monument. Leaving Bennington, you’ll drive up Route 7. You’ll follow this all the way to Burlington, with numerous possible sites to check out along the way. 

A couple of my favorites:

• Northshire Bookstore in Manchester: one of New England’s top independent bookstores
• Vermont Cookie Love in Ferrisburgh: incredible cookies, right along your route

Finally, you’ll be in Burlington. This is Vermont’s largest city and there is so much to do, including checking out the dozens of local breweries. Don’t miss views over stunning Lake Champlain either, especially at sunset. 

So now you know what the best road trips from Boston are! These road trips not only have an incredible destination to explore, but also include a beautiful drive (if taken during the right season!)

And, if you are looking for more Northeast cities to explore even after reading this, I’ve got you covered! Philadelphia is one of the best cities in the Northeast, with so many free things to do making it an affordable trip!

While I always recommend exploring a city enough to get a feel for it, Philadelphia is compact enough that you can easily craft a 1 day itinerary to explore much of what the city has to offer!

in it for later

Jess is a medical student in the midwest, with a HUGE passion for travel and wine tasting. When she is not found at the hospital, you can find her playing with her mini Australian Shepherd or planning her next vacation! She created Travel + Tannins to help inspire and plan travel (wine related, or not!) for others.

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7 Spectacular Weekend Road Trips from Boston, Massachusetts

Posted by Sarah Lamagna May 25, 2021 Updated April 11, 2023

Tired of the cobblestone streets and “R’s” left out of every word? Luckily for the residents of Boston, there are some epic weekend road trips within a few hours of the city.

Boston might be home to some incredible sights and truly dedicated sports fans, but sometimes a weekend away is just what the doctor ordered.

Whether you’re looking for gorgeous coastal villages, quaint mountain towns, some good ol’ fashioned Ben & Jerry’s ice cream, or views from the top of Mount Washington, we’ve got what you need.

Related Read:   10 Chill Romantic Getaways in Massachusetts

Road Trip Planning

Before you head out, make sure to plan accordingly. Unlike a lot of other places across the country, weather and traffic are fairly predictable in and around Boston. There usually aren’t “surprise” storms and traffic is, well, always there.

Expect typical weather patterns during corresponding seasons: it snows in the winter, rains in the spring and fall, and is hot/humid in the summer. You won’t need any special car enhancements (like four-wheel drive) to get to any of the places on this list. But beware of potholes – they are a’plenty in the northeast. Construction crews never seem to be able to keep up with them.

Speaking of construction; it’s constant in New England and especially in Boston. Construction crews are out in freezing temperatures and rainy days. Expect traffic to be slower and heavier in these areas. It’s also important to note that depending on your destination from Boston, you might pass through several rush hours.

There’s also a reason that Boston drivers are well-known across the country; they are aggressive. Come prepared knowing that if you stall too long when a red light turns green, you will definitely be beeped at – car horns are the state bird call of Massachusetts…just kidding.

Pro tip: do NOT dilly dally in the passing lane. This is a huge pet peeve of most New Englanders. If you aren’t passing someone, get out of that lane.

Related Read: 5 Best Day Trips From Boston for Scenic New England Getaways

7 Amazing Weekend Trips from Boston

1. north conway, nh.

This picturesque town has everything you’ll need for outdoor adventure. North Conway is in the heart of White Mountain National Forest which prides itself in a myriad of outdoor activities including hiking, biking, skiing, and fishing (among others).

Mount Washington looms in the distance as if beckoning you to climb it. At 6,288’ above sea level, Mount Washington is the tallest mountain in the northeast. You can climb it anytime of year (although we recommend a guide service like Nemo Mountaineering in the winter) through several routes, with the Tuckerman Ravine route being the most popular. You can also drive up yourself during the late spring/summer months or take the Cog Railway .

The heights around Mount Washington aren’t for everyone, though. Instead, you can take a drive along the Kancamagus Highway (the Kanc to locals). It can get busy on the weekends, especially during peak leaf-peeping season in the autumn.

You can also simply hang around town: visit Zeb’s General Store , grab brunch at Peach’s Restaurant , drink a beer at Moat Mountain Smokehouse and Brewing , or visit the Conway Scenic Railroad .

• Distance from Boston : 137 miles
• Drive time: 2 hours, 30 minutes

2. Westerly, RI

Head on down to this southern Rhode Island beach town to catch some waves and rays (and maybe a glimpse of TSwift ). It’s the shortest trip on our list from Boston which means extra time to soak in the sun and get that tan you’ve been yearning for.

The best place for getting in that vitamin D is at Watch Hill . It’s great for kids and adults alike and includes a Merry-Go-Round where kids can take their chances grabbing brass rings for a shot at a free ride – psst…make sure to grab an outside horse to do this.

Aside from beaches, there’s plenty of other things to do including popping your head into a few boutiques like Anther Living and Rochelle’s . For some good food (or a great place to stay), check out Ocean House’s many culinary journeys including a taco shack, a secret garden creperie, and a raw bar – among so much more.

• Distance from Boston : 92 miles
• Drive time: 1 hour, 30 minutes

3. North Adams, MA

Grab a wand and your spell book to head to the place that inspired writers like J.K. Rowling, Henry David Thoreau, and Herman Melville. Located in northwestern Massachusetts, North Adams is in the heart of the Berkshire Mountains.

You can head up to the top of the state to visit Mount Greylock and the Massachusetts War Memorial Tower. On a clear day, you can see for 70 miles in either direction into five states.

Too bad you didn’t really know magic, though, and get yourself back down to town quickly. Whenever you do, head over to PUBLIC for some great eats and then to Bright Ideas Brewing for the best brewery in town.

• Distance from Boston : 136 miles
• Drive time: 2 hours, 45 minutes

Related Read: 10 of the Best Airbnbs in Boston, Massachusetts

4. Lake George, NY

If you’re in the mood for some lake-living, then Lake George is your answer. It’s full of every type of water-related activity you can think of: boating, kayaking, water skiing, canoeing, fishing, and even hopping on a cruise . But if water isn’t your thing, well, maybe go elsewhere?

Seriously, though, on top of every water sport in the world, Lake George has many land activities. For the most unique experience on land, though, consider taking a rail bike tour through the Adirondacks. Or you could check out the Natural Stone Bridge and Caves , which is home to the largest marble cave entrance in the eastern United States.

• Distance from Boston : 227 miles
• Drive time: 3 hours, 30 minutes

5. Mystic, CT

Move over Leonardo Dicaprio, Mystic is the true home of the hero of the Titanic. That is, Bob Ballard who discovered the famous ship wreckage. He founded the Institute for Exploration which partnered with the Mystic Aquarium – located in, you guessed it, Mystic.

But this quaint, coastal town is more than marine ecosystems. You can travel back in time and visit Mystic Seaport Village and set foot on a veteran training ship . If you need to pick up some trinkets for your family or friends, head to Franklin’s General Store in Olde Mystick Village . Grab a pizza slice from famed Mystic Pizza (yup, it’s the same one in the movie starring Julia Roberts). To wind down for the evening, get a scoop of ice cream from Mystic Drawbridge Ice Cream and watch the boats head down the Mystic River.

• Distance from Boston : 100 miles
• Drive time: 1 hour, 40 minutes

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

6. Stowe, VT

No matter the time of year you visit this northern Vermont town, Stowe is perfect for any traveler. Into skiing? Head to Stowe Mountain Resort . Rather have a spa day? Then Stoweflake is your destination. Or maybe you just want some ice cream? Then take a tour of the hippie owners’ flagship Ben & Jerry’s store in Waterbury (just south of Stowe).

A trip to Stowe isn’t a trip, though, until you visit the Trapp Family Lodge . You can stay there the entire weekend, grab a beer from the von Trapp Brewery , or experience one of the many activities there including disc golf, biking, hiking, and carriage rides.

Pro tip: don your best dirndl or lederhosen during their Oktoberfest . It’s a heck of a time!

• Distance from Boston : 199 miles
• Drive time: 3 hours

7. Kennebunkport, ME

Kennebunkport is THE quintessential New England coastal town. To get a real feel for its personality, head on out to Dock Square where you can peruse art and buy some fashionable clothing at the boutique shops or sit in one of the many cafes along the main drag.

Get your lobster fix at Port Lobster or Mabel’s (they’re both favorites for the locals) or try the famed Whoopie Pie found at HB Provisions . For adventurous souls, visit the Rachel Carson National Wildlife Refuge or kayak around Cape Porpoise Pier . End your day by resting your head (or simply walking around the 60 acres of lush gardens) at St. Anthony’s Monastery and Franciscan Guest House .

• Distance from Denver : 84 miles

Explore New England

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10 Best Massachusetts Airbnbs for a Unique Weekend Getaway

15 Best Hiking Trails Near Boston, Massachusetts

12 Best VRBOs in Maine for a Unique Vacationland Getaway

10 Super & Secluded Maine Cabin Rentals

10 of the Best Airbnbs on Cape Cod, Massachusetts

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

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Seen in: Massachusetts , New England , Road Trips

Posted by Sarah Lamagna

Sarah is an ecologist-turned-freelance writer specializing in the ecotourism and slow/sustainable travel industry. Her bylines include The Denver Post, 5280 magazine, VeryWellFamily, Matador Network, and was an expert on NPR’s The Takeaway for her work on the wildfires in Colorado.

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

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With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Find a Lincoln Airbnb or stay in North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

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New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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Discover New England Itinerary

12 days,  11 nights.

The following suggested road trip, self-driving itinerary gives you the opportunity to base yourself at just two different locations in New England, experiencing the diversity of the landscapes from very different parts of the region. This is a great itinerary if traveling with small children.

Day 1 — Boston to the Southern Maine Coast

If this is your first visit to Boston , we recommend at least a three night stay. For the repeat visitor there is always lots to see again, so we suggest you spend a couple of nights to reacquaint yourself with the city. Generally speaking, it is a good idea to stay at least one night in Boston if you have a late afternoon or early evening arrival into Logan from a transatlantic flight. An early afternoon arrival into Boston eliminates the need to overnight that first evening in Boston and could head out of the airport to your first stop outside of your gateway arrival city. For planning purposes, we will begin outside of Boston. Travel north to the Kennebunks, less than a two hour drive from Boston's Logan Airport.

Day 2 — Southern Maine Coast

For a chance of scenery and an opportunity to see the wonderful and dramatic rocky coastline of Maine, head to the southern coast area of the Kennebunks .  Visit The Kennebunks which includes Kennebunkport , summer home the Bush family and home to the Seashore Trolley Museum with a four mile ride. Then, hop over to  Ogunquit , the perfect seaside holiday destination with long sandy beaches. Great for families and couples alike, this area is abundant with activities including the increasingly popular sea kayaking. See the spectacular Perkins Cove, or take a lobster boat ride from the pier.

Day 3 — New Hampshire Lakes Region

Enjoy the delights of being in this picture perfect lake front setting of Lake Winnipesaukee . This vast lake dominates the region, and there are fine places to enjoy the charms of the lake and its many islands. You can cruise aboard the M/S Mount Washington or take a paddle yourself and go kayaking!

Day 4 — New Hampshire White Mountains Region

Within a short drive of the lakes region you are in New Hampshire's White Mountains . Enjoy driving through some of the prettiest villages in New England. Hike to the top of Mount Washington, the tallest mountain in New England (6,288 ft) or take the eight mile toll road to the top. If traveling with children, take advantage of some of the great family attractions throughout the White Mountains such as Storyland  or  Santa's Village .

Day 5 — Central Vermont

Just under a two hour drive from the Lakes Region is Woodstock, Vermont . Settled in 1768, this picture perfect Vermont village retains the elegant charm and rugged character of American antiquity. With a covered bridge in the middle of town and stately homes surrounding the village green, it is easy to see why Woodstock has been called the "quintessential New England village." Take a stroll through its downtown and discover unique shops, galleries, artisan studios, country stores and fine restaurants. Time allowing, tour Billings Farm & Museum , an agricultural museum that recreates farm life of last century where you can experience the agricultural traditions of cheese making and maple sugaring. Quechee, VT is also worth a visit. AT the Simon Pearce Mill and Showroom  right in the village, watch glass and pottery in the making. As you head back to the Lakes region, stop in Hanover , located right on the Connecticut River and home to Dartmouth College . A picture perfect college town set around a lovely town green, Hanover makes a great lunch or coffee stop. Don't miss the Hood Museum , a small but beautifully designed art museum right in the center of town.

Day 6 — Cape Cod, Massachusetts

Drive south today to Cape Cod, Massachusetts . With its sandy beaches, rolling dunes and old world charm, Cape Cod has long been America's playground. On ' The Cape ' (as it is known), the Old King's Highway (or Rte 6A) runs through several small villages, each distinct, yet filled with the specific charm of the Cape.

Day 7 — Cape Cod

Get to know this wonderful area of New England. Explore the 43,586 acre Cape Cod National Seashore by pedaling the 25.1 mile Cape Cod Rail Trail or taking clubs to one of the Cape's 27 public-access golf clubs . For a day of culture, visit the  Heritage Museums & Gardens  with its unqiue Americana and antique cars, stop into  the Cape Cod baseball League Hall of Fame . In the port of Woods Hole , the mysteries of ocean life are on display at the NOAA Aquarium and the Oceanographic Institution , and a Cape 'must-see' attraction is the seaside resort town of Hyannis, the summer home of the Kennedy family and the John F. Kennedy Memorial and Museum .

Day 8 — Whale Watching

While you can whale watch all along the New England coastline, Cape Cod offers the closest views of Stellwagen Bank, one of the primary feeding grounds of the many humpback whales, finback whales, and minke whales as well as dolphins and porpoises that migrate to the New England waters. During your approximately three-hour excursion, you will learn from experienced naturalists how to identify the humpback and finback whales due to pigmentation and markings on their backs. Take advantage from other great excursions such as deep sea fishing, harbor cruises and also floating classroom trips to learn more about the marine life around Cape Cod.

Day 9 — Martha's Vineyard Or Nantucket

Day trip to martha's vineyard.

Just a short ferry ride (approximately 35 - 45 minutes) from the mainland, the Vineyard features pristine sandy beaches, golf courses and great natural beauty. In Oak Bluffs , marvel at brightly painted ' gingerbread cottages ,' which began as a 19th century Methodist summer campground. Vineyard Haven is another picturesque community as well as the island's year round ferry port. Edgartown is an elegant yachting center, its streets still lined with whaling captain's stately homes. The island also has five light houses, all originally built in the 1800's and subsequently replaced, and in some cases, moved back from the encroaching sea. The Gay Head and East Chop Lighthouse are open for sunset tours. Best way to get around the island is either by rental car or a sightseeing tour or taxi. Bicycles are also available at numerous locations.

Or Day Trip to Nantucket

Thirty miles off the Massachusetts coast, this crescent shaped island is in a world by itself. Cobblestone streets and an array of Georgian, Federal, and Greek revival homes reflect Nantucket's history as a prosperous whaling port. Quieter that Martha's Vineyard, Nantucket is a great place to adjust to slower pace of life, and visit the unspoiled beaches, solitary lighthouses and acres of conservation land. The best way to get around is by bicycle, and there are many places to rent a bike upon arrival on the island. Note: if you have an additional day, visit both Martha's Vineyard and Nantucket

Day 10 — Newport, Rhode Island

A short drive (approximately one and half hours from Falmouth on the Cape) brings you along the coast to Newport . An easy day trip from most points along Cape Cod, Newport is well worth the visit. Famous for its 19th century Gilded Age mansions , these 'summer cottages' (as they were known) were built by America's fabulously rich and famous industrialists are filled with gilt, marble, antiques and treasures. The Newport Preservation Society now runs the mansions, which are open for public tours. Other highlights include the three mile Cliff Walk that gives you a spectacular view of the mansions and the ocean. Be sure to visit the International Tennis Hall of Fame and Museum where the rich history of tennis is chronicled. You can even play on the oldest grass tennis courts in the world!

Day 11 — Plymouth

A short drive north of the Cape is Plymouth . Plymouth is home to the 'Plymouth Rock' and the Mayflower II, enduring symbols of the Pilgrim's arrival in the New World. The region also offers picturesque harbors, historic lighthouses, and acres of cranberry bogs that turn ruby red as harvest time approaches. Plymouth bills itself as "America's Hometown". The colonists' struggle to build a new community and their relationship with the indigenous Wampanoag are brought to life at Plimoth Plantation , a recreation of the 1627 Pilgrim community. You can interact with costumed interpreters and learn more about their daily life in the New World.

Day 12 — Depart Boston

Today, you head north back to Boston. From the beginning of the Cape, this drive will take you approximately 60-90 minutes. From the tip of the Cape at Provincetown, it will take approximately one hour more. You can also take the ferry from Provincetown to Boston which takes approximately 45 minutes but bear in mind that this is a passenger ferry boat only — no cars are allowed.

Happy Travels!

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Vacation packages from Boston

We have many options for vacation packages from Boston with deals on hotels, flights, and cars, and you’ll earn extra savings by bundling. Take the family on an Orlando vacation or treat your partner to a romantic vacation in Niagara Falls . Customize your journey and select hotels, flights, and cars that best suit your budget and your needs. Compare prices for different dates and locations and use our many search features.

Weekend getaways from Boston

Take off for a quick jaunt from the city to experience luxury hotels, cheap stays, and more. With Expedia’s weekend vacation packages from Boston, you could head to the beaches of Cape Cod or forests of Vermont. Discover Maine with a romantic weekend vacation package, spent cycling the coast and dining on the waterfront. Or see pristine beaches and countless lighthouses with an excursion to Nantucket, MA. For family weekend getaways from Boston, consider the Hudson Valley or Pocono Mountains, where you can go horseback riding or try rock climbing and archery.

The best road trips from Boston

Discover incredible road trips from Boston for a great price on Expedia. Combine car rentals with hotels in one of our vacation packages from Boston for couples to Martha’s Vineyard romantic hotels . Plan a New England road trip from Boston to NYC with friends and stop in Cape Cod and Newport along the way. We have packages for luxury hotels and prestige vehicle rentals in our vast inventory, or cheap cars and budget hotels.

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Take all-inclusive vacations from Boston and get all your costs upfront. Get meals, drinks, taxes, and fees included in the hotel price and score additional discounts by bundling travel bookings together.

We have fantastic deals for all-inclusive hotels in Miami . Bundle your favorite hotel with a car rental and/or flights to save even more. All-inclusive vacations from Boston to popular beach spots are great for families, couples, and friends. Save by getting meals and drinks included, plus extra discounts on your overall trip cost with a package. Check out vacation packages to Costa Rica to get started.

Boston winter vacations

Take the family on winter getaways from Boston to popular ski destinations like New Hampshire or Vermont. Or plan a holiday for the holiday season in beautiful cities to celebrate in, like Washington D.C., or New York City. There are many wonderful destinations to take weekend getaways from Boston in the winter.

Last-minute vacation deals from Boston

Expedia has last-minute vacation deals from Boston. We source offers for all travelers at attractive prices—even if you are late in the game. Our deals on last-minute getaways from Boston find you savings on properties of all types. And whether it’s a spontaneous trip with your sweetheart or a delayed flight that’s got you traveling, find what you’re looking for on Expedia. We have a large inventory of travel options across various budgets and catering to many different types of experiences. Find cheap hotels close to airports, luxury stays in the best locations, or accommodations in all the towns you stop at along your road trip.

Flexibility and cancellation

Find information about your vacation booking in your itinerary under ‘My Trips.’ To book flexible getaways, choose hotels or car rentals with ‘free cancelation’ and flights with ‘no change fees.’ Learn more at our customer service portal . 

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A “Genius” New England Road Trip Itinerary- College Towns!

Looking For a Northeast Road Trip Itinerary?

If you’re looking for a fun and unique New England road trip itinerary…we’ve got you covered!

This week’s New England road trip itinerary is a guest post from Sara with Journey of Doing . Sara believes the best way to tour New England states is by doing a northeast road trip through all these super cute New England college towns!

So, if you’re looking for a family road trip from Boston, need to make some college visits, or maybe just want to check a few New England states off your USA bucket list, this might be the perfect itinerary for you!

Boston is the perfect place to start or end this road trip! There are so many things to do in Boston with kids , teens, and families! It’s one of our favorite cities and definitely deserves a spot on any New England road trip itinerary!

Our New England Road Trip Itinerary

Day 1: Arrive Boston- Road trip 2 hours to Hanover, New Hampshire Day 2: Hanover, New Hampshire Day 3: Road trip 3 hours to New Haven, Connecticut Day 4: New Haven, Connecticut Day 5: Road trip 1.45 hours to Providence, Rhode Island Day 6: Road trip 1 hour to Boston, Massachusetts Day 7: Boston/ Cambridge, Massachusetts Day 8: Depart Boston 

Are we there yet? Check out our epic list of 250 road trip questions to keep everyone entertained along the way!

Day 1:  Arrive Hanover, New Hampshire

Home to dartmouth college.

The most cost effective way to get to Hanover is by driving from Boston.  Upon arrival, walk down Main Street to check out the local shops or head to the Dartmouth Green with a book, a ball, or a Frisbee. 

If you want to feel like a college kid, grab pizza and beer at Ramunto’s Brick and Brew .  If you’re looking for beer (and pub fare), head to Murphy’s instead.  If you are looking for a more upscale dining experience, head to Pine at the Hanover Inn.    

Evenings in Hanover are quiet.  See what’s happening at the Hop or check out the Dartmouth Observatory on Friday nights.

Hotel Suggestion:  Hanover Inn for 2 nights

Day 2:  Hanover, New Hampshire

Today is a great day to live out your Great British Bake-Off dreams by taking a class at King Arthur Flour .  Whether it’s bread, pasta, pie, or pizza, you’re sure to emerge with something delicious.  If you’re already a professional chef, grab fresh pastries from their bakery and head to their store for all the things that you can’t find at your local grocery store.  You’ll have to cross state lines, but luckily, it’s only a 10-minute drive.   

If getting your hands dirty doesn’t appeal to your sensibilities, you can revisit history through art by visiting the Orozco Murals or Hood Museum .   Quechee State Park offers a variety of trails and outdoor activities.  If it’s raining, head to the Montshire Museum of Science for a variety of STEM exhibits and activities. 

Day 3:  New Haven, Connecticut via Northampton, Massachusetts

Home to yale university.

Make a leisurely drive to New Haven by stopping in Northampton, home of the Calvin Coolidge Presidential Library .  (You can pick up a Presidential Library passport or collect another stamp in your existing one.)

Enjoy a delicious lunch at Viva Fresh Pasta .   Before getting back in the car, stretch your legs at the Smith College botanical garden s.  If you just want a quick stop, grab anything with the hot fudge at Herrell’s ice cream.  

A full day of driving requires an easy dinner.  Make it easy on yourself and head to Frank Pepe , a New Haven institution, for coal-fired pizza and beer. You can walk next door for dessert before heading back to your hotel.  

Hotel Suggestion:  New Haven Hotel for 2 nights

Day 4: New Haven, Connecticut

Before you start your day, see if you can get tickets to one of the Yale School of Drama productions.  You might just see the next Broadway or Hollywood star before they make it big.

Get an additional cultural fix by checking out any of the amazing collections at Yale.  While there are certainly more than these exhibits, these are some of our favorites!  Led by graduate students, the Yale University Art Gallery offers guided tours specifically curated based on what the guide is studying!  If you’re more of a book nerd, head to the newly renovated Beinecke Rare Book and Manuscript library to see the Gutenberg Bible and the original 1742 Yale Library collection. Or, if you’re more musically inclined, head to the Yale Collection of Musical Instruments .     

Regardless of what you choose, you’ve earned a treat.  You’ll want to hit up the Shops at Yale for retail therapy and ice cream at Arethusa .

Pre-show dinner options include Olea or Union League Cafe but make sure to make an early reservation so you can make it to the theater on time!

Day 5:  Providence, Rhode Island

Home to brown university, rhode island school of design, & johnson and wales.

Start your day early so you can make it to Providence when the RISD Museum opens.   

Grab a burger and milkshake at Harry’s Burger before heading to Roger Williams Park .   Whether you head to the zoo, the Museum of Natural History, or the botanical gardens, there’s plenty of ways to enjoy your afternoon. 

Try to plan your visit around the monthly WaterFire Festival .   Not only is it beautiful, but it is also a great way to experience the local art scene in Providence with music, art, and local restaurants.

Hotel Suggestion:  Courtyard Providence for 1 night

Day 6…7…8:  Cambridge/Boston, Massachusetts

Home to harvard, mit, & boston university (and many more).

Between the Freedom Trail, the museums, the seaport, and the green spaces, you could spend your entire vacation in Boston without ever crossing the river.  Sticking with the college town theme of this itinerary, I am sharing my favorite things in Cambridge, Massachusetts.

Choose a Harvard museum (or two).   With the largest endowment in the world, Harvard has some world-class collections.  I recommend the Harvard Art Museums or the Harvard Semitic Museum .   

If you can’t do any more museums, check out the local retailers, street musicians and festivals around Harvard Square.  I love perusing the many bookstores, especially the used books in the basement of that Harvard Bookstore .  

You’re going to want your walking shoes this afternoon.  Head to Mass Ave and start walking towards MIT. After 2.5 miles, you’ve earned a sweet treat from Toscanini’s .  (I recommend B3!)  Grab a table outside and rest your legs.  (You can also take the T.  It’s only two stops.)    

After ice cream, it’s time to choose your own adventure!  You can do a self-guided tour of the public art at MIT.  (Bonus points if you crack the alleged code on the Jaume Plensa sculpture!)   Or, you can explore innovation at one of the world’s leading technology institutes by visiting the MIT Museum .

Depending on where you are staying, head to Harvard Square or Kendall Square for dinner.  Harvard Square recommendations are Toscano , Harvest , or Grafton Street Pub .  Kendall Square recommendations are Legal Sea Foods , Oleana , and Amelia’s .

Don’t forget to check out the Harvard Box Office for public events.  Whether it’s hearing a guest lecture, attending a musical performance, or heading to a sporting event, there’s no shortage of events in Cambridge.

Once you’ve exhausted all the things to see in Cambridge, you can head across the Charles River and find everything from the Freedom Trail , to the Red Sox, to more museums and a Presidential Library !  You’ll want to grab a hazelnut chocolate chip cookie or two from Flour Bakery to fuel up though!

Hotel Suggestions:  The Charles Hotel or the Doubletree Suites Cambridge (it’s a short walk across the river from Cambridge) for 2 nights.

For more things to do, check out this great 2 day Boston itinerary .

Best New England Road Trips

Small New England towns have the most charm and are definitely worthy of a visit. Add Boston to the itinerary and you have a mix of a bigger city to round out your travels!

For these reasons we definitely feel like this might just be the most amazing New England road trip itinerary you can accomplish in just over a week. If you’re limited by time, you can certainly make this into a one week road trip from Boston. If you have more time consider this epic Boston to Niagara Falls road trip !

Have you been to New England? Have you visited any of these towns?

Road Tripping

We just love a road trip and think it belongs on every bucket list! Here are some more fun and exciting road trip ideas all over the US to inspire your travels:

20 Short Southeastern US Road Trip Ideas

20 Adventurous USA Road Trips

NC Road Trip Itinerary

Utah and Arizona Road Trip Itinerary

10 Must Do Southern Road Trips

10 Epic Pennsylvania Road Trips

Be sure to share all your epic adventures on Instagram with these fun road trip captions and quotes !

About The Author

A huge thank you to Sara from Journey of Doing!! Make sure to follow Sara on Instagram , Facebook , and Twitter !

Sara loves learning about local cultures, history, and traditions through travel. She’s recently written all about her time in Rome, including tips for driving in Italy , which I’m super excited about since I’m all about a road trip lately!

Stay tuned for more road trip posts coming up…so many fun road trip itineraries to share! But in the meantime, check out my favorite California road trip itinerary or any of these North Carolina weekend getaways !

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I love this idea! What a fun intinerary. Will have to note the locations next time we are in the area. Pinning for future reference!

Awesome! I hope you’re able to add a New England road trip to your schedule! It’s a beautiful area!

I’ve always wanted to explore more of New England. This is the perfect itinerary. I can’t wait to try it out.

It’s a beautiful area of the USA- I hope you do get to visit!

Very interesting, good job and thanks for sharing such a good blog.

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USA Tours & Trips from Boston

Find your perfect adventure! We have 14 tours of USA that start in Boston, USA. The most popular month is October, and tour lengths range between 5 and 13 days.

14 USA tour packages from Boston with 616 reviews

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Spotlight on Boston

I was a little nervous before the start of the trip because there were some complications trying to confirm the trip. It was partially my fault because I did book the trip relatively last minute, but I do believe there was some miscommunication on both ends that could have been avoided from the very beginning. The biggest problem was the method of communication. I did not understand that in order for the information to be relayed correctly, you had to message through the communication portal on touradar's website. That was not explicitly made clear, and it took several days and conversations with multiple people to finally realize that. Once that was made clear, everything ran much more smoothly, but I definitely think for the customer's sake especially new customer, someone needs to be very clear in explaining that and confirm with the customer by having them relay it back to them. Thankfully, once everything was booked and confirmed, the trip ran wonderfully! I had such a blast. My tour guide was amazing and the group I was with were incredible. I am definitely looking forward to booking another trip in the future.

New England's Fall Foliage (Classic, 8 Days)

Great tour guide and other personnel. Most hotels adequate to very good, especially the Trapp Lodge. Food adequate for the most part. Overall, a very nice trip and the colors were fantastic!

Colors of New England

• €150 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Colors of New England (Boston, MA to Portland, ME)

Boston Cape Cod & The Islands (Classic, 8 Days)

Cons: 1. Daniel Webster Inn was over-rated. Would not stay there again. 2. Visit to the Plimouth Plantation was a waste of time. Spent way too much time there. 3. Transportation from Logan Airport to the Boston Hyatt was a mess!!!! No signs, no directions, and the taxi driver had no idea what to do with the voucher. Ended up paying for the taxi! Ridiculous!! 4. Service at the included dinner at the Daniel Webster Inn was horrible!! Kathy (our waitress) should be fired! However, the food was delicious! 5. Not enough time spent in Nantucket. 6. Way too much time spent at the Breakers in Newport. 7. This should not be considered an 8-day tour. All we did on day 8 was ride on the bus to the airport! Pros: 1. Tour director Robin was outstanding!! Wellness director, Brittany, was also fabulous! 2. Canolis, Cape Code Chips and Cape Codders on the bus was a nice touch! Thoroughly enjoyed the snacks on the bus! 3. Ferry to Martha's Vineyard was fun! Thoroughly enjoyed the talk session/information about the Martha's Vineyard Camp Meeting Association. Very interesting. 4. Local guide tour of Nantucket Island was great! Lots of interesting information. Not enough time spent in Nantucket. 5. Loved the Harbor View hotel! 6. Sailing on the Adirondack II was THE BEST!! Need to offer more than one Mimosa! 7. Luggage service was great.

Classic Fall Foliage

I was on a fall foliage tour with Globus. The guide was great, the itinerary was also very nice and I enjoyed it very much. I was however disappointed that despite Globus claiming on their website that they have "small group" tours that average 24 people there were 42 on our tour. I guess I should look for advertisement of the total group size instead of thinking that an "average" of 24 would be closer to 24 than to 42! Proof of vaccination was required, which was necessary for me to sign up in the first place but I truly felt deceived that my "small group" was almost double the average.

Cape Cod & the Islands

Exceptional itinerary, tour director, and coach driver.

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Colours of New England

Our guide, Yvonne DeWit, was excellent! Organized, knowledgeable, informative. Interesting variety of stops from rugged Maine to quaint Vermont to historic Boston with much in between. Would highly recommend this tour and look forward to another one.

Fall Colours of New England (10 Days)

The tour experiences, excellent work by tour director Pam and most of the hotels were wonderful. Having grown up in the east, now living in the west, I loved seeing the autumn leaves and delightful small towns. Overall, this tour was a bit too strenuous for me at the age of 81 and with arthritic knees.

Boston Cape Cod & The Islands (Small Groups, 8 Days)

New England and the Hudson Valley

New England's Fall Foliage (Small Groups, 8 Days)

Notably New England

I joined a Travelling Time tour which was music themed (not mentioned in the initial enquiry). I don’t like country music but somehow that didn’t spoil a tour with a good natured group of people. I was one of three octogenarians and felt I was looked after well. Several of the group had travelled with this company for years ! There was a feeling that not enough research had been done regarding places to stop and places to eat. Personally I would have liked to see a little more of places and regretted not going round Mark Twain’s house in Hartford. Two “free” days in Boston and Martha’s Vineyard were really pleasant spent with a few of the group. It was a bit disappointing to find that two evening meals and breakfast were the only meals included in the tour. The hotels were very comfortable. The Waterbury, Vermont one was the most attractively situated. The coffee machines rarely worked. For me, anyway

Tours starting from Boston

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40 Best Stops Between Raleigh and Boston

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How long is the drive from Raleigh to Boston?

The direct drive from Raleigh to Boston is 723 mi (1,163 km) , and should have a drive time of 11 hrs 47 mins in normal traffic.

If you’re going on a road trip from Raleigh to Boston, we did the research for you and compiled some great stops along the way — with New York City , Washington DC , Philadelphia , Baltimore , Williamsburg , Gettysburg , Newport , Atlantic City , Richmond , and Brooklyn , as well as top places to visit like Busch Gardens Williamsburg and Smithsonian National Museum of Natural History, or the ever-popular Colonial Williamsburg Visitor Center.

Top cities between Raleigh and Boston

Williamsburg.

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Philadelphia

Atlantic city.

Best stops along Raleigh to Boston drive

Colonial williamsburg visitor center.

Busch Gardens Williamsburg

Smithsonian national museum of natural history.

Smithsonian National Air and Space Museum

National Gallery of Art

Gettysburg National Military Park Museum & Visitor Center

United states naval academy, horseshoe casino baltimore.

National Aquarium

Strasburg Rail Road

Cape may beach nj, longwood gardens, harrah's philadelphia casino and racetrack, independence hall.

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Atlantic city boardwalk, sesame place philadelphia, six flags great adventure, 9/11 memorial & museum, the high line, empire state building, top of the rock, central park, woodbury common premium outlets.

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Walkway Over the Hudson

Norman rockwell museum, mystic seaport museum, the breakers, top searches in boston, other popular road trips from raleigh, explore nearby places, all related maps of boston.

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Boston throughout the year

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Looking for day-by-day itineraries in Boston?

Get inspired for your trip to Boston with our curated itineraries that are jam-packed with popular attractions everyday! Check them out here:

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Frequently Asked Questions

Can i drive from raleigh to boston.

Yes! You can drive from Raleigh to Boston.

How far is Boston from Raleigh by car?

The drive from Raleigh to Boston is 723 miles (1,163 km).

How long does it take to drive from Raleigh to Boston?

Driving from Raleigh to Boston should take you 11 hrs 47 mins in normal traffic.

How much would gas cost from Raleigh to Boston?

Gas from Raleigh to Boston would cost around $63 to $148 , depending on your vehicle's fuel efficiency.

Where should I stop on the way from Raleigh to Boston?

You could check out Busch Gardens Williamsburg and Smithsonian National Museum of Natural History, or the always popular Colonial Williamsburg Visitor Center!

What are the best cities to visit between Raleigh and Boston?

People love visiting New York City, Washington DC, and Philadelphia, among others.

What's the weather like in Raleigh?

It depends on when you visit! We've compiled data from NASA for each month of the year: see the links below for more information.

• Weather in Raleigh in January
• Weather in Raleigh in February
• Weather in Raleigh in March
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• Weather in Raleigh in May
• Weather in Raleigh in June
• Weather in Raleigh in July
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What are some other road trips from Raleigh?

There are plenty! Below you'll find links to all the road trips we've assembled for Raleigh.

• Raleigh to New York City drive
• Raleigh to Washington DC drive
• Raleigh to Orlando drive
• Raleigh to Chicago drive
• Raleigh to Myrtle Beach drive
• Raleigh to Savannah drive
• Raleigh to Gatlinburg drive
• Raleigh to Charleston drive
• Raleigh to Atlanta drive
• Raleigh to Williamsburg drive
• Raleigh to New Orleans drive
• Raleigh to Philadelphia drive
• Raleigh to Boston drive
• Raleigh to Baltimore drive
• Raleigh to Nashville drive
• Raleigh to Toronto drive
• Raleigh to St. Augustine drive
• Raleigh to Niagara Falls drive
• Raleigh to Montreal drive
• Raleigh to Charlotte drive
• Raleigh to Virginia Beach drive
• Raleigh to Richmond drive
• Raleigh to Miami Beach drive
• Raleigh to Asheville drive
• Raleigh to Memphis drive
• Raleigh to Wilmington drive
• Raleigh to Tampa drive
• Raleigh to Pittsburgh drive
• Raleigh to Cleveland drive
• Raleigh to Gettysburg drive

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Ohio to Boston drive

Ohio to boston road trip planner.

Here's a sample itinerary for a drive from Ohio 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.

9:00 am  start at Ohio drive for about 2 hours

10:50 am   Cleveland stay for about 2 hours and leave at 12:50 pm drive for about 2 hours

2:39 pm   Erie stay for about 1 hour and leave at 3:39 pm drive for about 1.5 hours

5:04 pm   Allegany State Park stay for about 1 hour and leave at 6:04 pm drive for about 1.5 hours

day 1 driving ≈ 6.5 hours find more stops

10:00 am  leave from Buffalo drive for about 2.5 hours

12:18 pm   Syracuse (New York) stay for about 1 hour and leave at 1:18 pm drive for about 2 hours

3:30 pm   Albany (New York) stay for about 1 hour and leave at 4:30 pm drive for about 3 hours

7:24 pm  arrive in Boston eat at Mike's Pastry stay at The Westin Copley Place

day 2 driving ≈ 7.5 hours find more stops

Where should I stop along the way?

Cleveland   (83 answers)     Rock and Roll Hall of Fame and Museum   (13 mentions)     The Cleveland Museum of Art   (12 mentions)     Rock and Roll Hall of Fame and Museum   (6 mentions)     West Side Market   (6 mentions)     Great Lakes Brewing Company   (5 mentions)     restaurants around Cleveland:         Lola         Lolita         The Greenhouse Tavern         Melt Bar & Grilled         L'Albatros     questions about Cleveland:         What's the best neighborhood in Cleveland for a first time visitor?         Good restaurants for business dinner?         What is your favorite restaurant in Cleveland?         New to the city, friend coming to visit: What should we do?         Fun things to do Erie   (4 answers) Allegany State Park Buffalo   (42 answers)     restaurants around Buffalo:         Anchor Bar     questions about Buffalo:         What is your favorite restaurant in Buffalo (New York)?         What to see other than the falls Syracuse (New York)   (22 answers)     questions about Syracuse (New York):         What is one attraction to see? Famous place to eat at? Albany (New York)   (19 answers)     questions about Albany (New York):         Leaving Albany, NY for 6 days, north or south?

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 Ohio drive , or go to the main page to plan a new road trip .

You can also compare the travel time if you're flying or driving by calculating the distance from Ohio to Boston . Or get a full Ohio 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 Ohio well, please help your fellow travelers and answer their questions about Ohio!

More info on this route:

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How to Take a Stress-Free EV Road Trip in the U.S.

It’s easier than ever to take an electric vehicle on a long road trip, if you bear a few things in mind before you depart..

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The U.S. boasts thousands of miles of roads that can be reached within a single EV charge.

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EV road-tripping probably conjures one of two images for you: an eco-friendly, quiet, emissions-free ride from the future—or a fraught nightmare of battery-range anxiety and roadside assistance. The truth is, it can be fully the former if you keep a few things in mind. I’ve driven a Polestar 2 some 300 miles from L.A. to Las Vegas and taken a multigenerational road trip to San Diego in a Rivian R1S. Both journeys were smooth, much cheaper by the mile, and infinitely kinder to the environment. Here’s a primer on taking an EV road trip of your own.

How range and recharging work

There are three main things to know when driving an EV on a road trip: how far the car can go on a full charge (known as its range), how long it takes to recharge the battery, and where to find charging stations (and what kind).

Ranges differ. Most modern EVs offer between 200 and 400 miles. Charging infrastructure likewise is not created equal. California leads the way , with New York, Florida, and Texas on its heels. Other states have made great progress; Colorado has been working on adding charging capabilities to its scenic byways for several years. The recent federal infrastructure bill is channeling $7.5 billion toward half a million more chargers by 2030. Finally, charging time also varies. A fast charger will get you back on the road within 30 minutes. Slower plugs can take as long as humans to recharge overnight. (The type of car you have and the size of its battery are also factors.)

Hertz and EVgo have teamed up to make borrowing an electric vehicle easier.

Courtesy of EVgo

Renting an EV

Car rental companies are a great place to take a test drive into the inevitable EV world. Hertz, for example, says it has tens of thousands of EVs at more than 2,000 sites in 44 states, and it’s building a fleet at a range of price points (although it has been in the news lately for selling off some of its fleet). The company has a quick guide to renting an EV on Hertz.com , with notes on charging and braking, and primers on different car models, as well as a partnership offering discounts with charging network EVgo.

The peer-to-peer car-sharing app Turo, meanwhile, launched an EV hub in April. It showcases three curated EV collections (budget, SUV, and luxury) and has tips on driving electric vehicles. The app offers 1,500 makes and models; EVs made up 9 percent of its listings at the end of 2023.

How to find an EV charger

ChargePoint offers the most locations in the United States, with more than 31,000 locations. Electrify America and EVGo are two other popular networks, with more than 900 and 950 charging stations, respectively. Electrify America has an explainer on topping up , including a note on the “charging curve” (charging accelerates in the middle of the session) and other considerations like compatibility. (There are a couple of different plugs , but most modern cars can connect with any of them). Added bonus? The network’s energy is 100 percent renewable via solar farms and renewable energy certificates.

When you plan your route, look for pit stops with at least four outlets, says Joel Levin, executive director of EV advocacy nonprofit Plug In America . That way you’re less likely to find them all in use. “Road-tripping in an EV can be a lot of fun, but it takes a little planning and a different way of thinking about your trip,” he adds.

Use maps and apps

There are two keys to a stress-free trip: maps and apps. Waze added EV charging stations in 2023. Google Maps updated its offering for Earth Day 2024, with more specific location information, forecasted energy consumption for trips, and more . And for EVs with Google Maps built in, including Polestar, Volvo, and Renault vehicles, the software will automatically suggest charging stops when you plan a trip. It also shows charging options at other businesses such as grocery stores.

The charging networks have their own apps, too, allowing you to add payment methods, find available stations, and monitor progress if you leave your vehicle for a while. PlugShare , meanwhile, is a free community-based app that shows nearby chargers and reviews from users.

Book a hotel with an EV charger

Another pro tip: Find hotels with plentiful plugs. With the right combination of high range, shorter distances, and overnight charging, you may not need to stop during your daily drives. The Hilton chain lets you filter your search by hotels with charging facilities (and displays more than 1,200 results in the United States alone). Marriott offers a similar filter; I found 1,172 hotels on a recent search. IHG Hotels & Resorts, meanwhile, has facilities at almost 1,200 hotels in the United States. Some 30 percent of Relais & Chateaux’s North American hotels have chargers.

“Booking a hotel without an EV charger adds a level of stress and uncertainty that is no longer necessary,” says Bruce Becker, owner of the net-zero Hotel Marcel in Connecticut and an EV owner since 2011. “EV drivers actually have an advantage over drivers with gas cars because you’ll wake up in the morning with a full charge, ready to hit the road.”

Becker, who is chairman of the state’s Electric Vehicle Owners Club, has plenty of recommendations for your first EV road trip. In the summer, he vouches for Cape Cod (“there are plenty of fast chargers along [Highways] 95 and 91”); in the fall, he suggests a foliage trip from Hotel Marcel to Woodstock, Vermont, or to Maine. In fact, most of the country can be road-tripped in an EV with a little preparation, making it fairly easy to take your foot off the gas.

Miami Heat | After notching win in Boston, Heat look to deny…

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Miami heat | after notching win in boston, heat look to deny celtics road-trip advantage.

Boston is 14-7 in its last 21 road playoff games, including five of seven games in Miami, with one being a victory in Game 7 of the 2022 Eastern Conference finals.

So, coming off a needed road win over their own on Wednesday, the Heat will try to flip the scrip t on the top-seeded Celtics and take a lead in the series in Game 3 (Saturday at 6 p.m.) and increase the advantage in Game 4 (Monday at 7 or 7:30 p.m.).

“We know what Boston’s going to come in here with,” Heat coach Erik Spoelstra said. “Even knowing that, it’s hard to create that edge, that urgency, all that. We had an unbelievable sense of urgency after Game 1 of getting absolutely embarrassed and feeling a certain way about that. And having that extra day to sit with that was horrible. And that can be motivating.

“I’m sure Boston feels the same way. We’re going to have to beat them, I’m sure, at their best version of what they bring.”

The Heat have not been bad on the road in crucial games, either. Last year, they went 7-6 in road playoff games. They picked up a series-clinching, overtime win against the Bucks in the opening round as well as two series-opening wins and a Game 7 against the Celtics in the TD Garden. In this opening series against the Celtics, they split the first two games on the road.

“I think just staying steady,” said forward Caleb Martin, who scored 21 points and drained five 3-pointers in Miami’s win on Wednesday. I think a lot of it (is) you know what type of environment it’s going to be. It’s going to be a lot of runs, especially in that building. The basket can get 8 feet wide sometimes for them. I think just staying steady, just knowing they’re going to have those runs and knowing it’s going to be explosive. As long as we just stay steady, mentally, we’ll be alright.”

Although the Celtics are favored to win the series, the Heat’s victory in Game 2 threw a wrench in Boston’s coronation. Miami and Boston have faced off six previous times in the postseason since 2010. The Heat have won four series to the Celtics’ two, and the last four playoff series have gone six or seven games.

“That goes back to, obviously, when the Big 3 was here,” center Bam Adebayo said. “It just is what it is. It’s a great rivalry. You know it’s going to be a dogfight series every time.”

If the Heat are going to win this series, they will need to go back to Boston at least once.

“You’ve got to come in there with that mentality that whoever gets on that bus, that’s who’s got your back,” Adebayo said. “That’s how you’ve got to look at it: going into the lion’s den.”

But before that, the Heat know they will get the Celtics’ best punch in Miami.

“It goes both ways,” Martin said. “Just like you feed off your home crowd, one of the best feelings in the game is to go into somebody else’s place, especially a hostile environment, and leave with a win. They’re going to try to do the same.”

Wright questionable for Game 3

Heat guard Delon Wright may miss Game 3 against the Celtics. Miami listed the guard as questionable due to personal reasons on its injury report Friday night.

Duncan Robinson (back), Kevin Love (arm) and Haywood Highsmith (arm) are all listed as available.

Star Jimmy Butler (knee) and guard Terry Rozier (neck) are both still listed as out for Game 3 with their lingering injuries.

More in Miami Heat

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Miami Heat | Dave Hyde: Heat can’t extend Butler’s deal — this good era is now gone

Miami Heat | So what now for Heat roster? A player-by-player look at every contract, potential next steps

Miami Heat | ASK IRA: Did Heat’s last men standing deserve better than being exposed?

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Add these 3 charming ontario towns to your summer bucket list.

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Beautiful Elora Streets; Ontario, Canada

Ontario is known for summer road trips and with warmer weather finally here it’s time to pick a small town and start exploring. Canada's second largest province covers over 415,000 square miles and borders the United States and the mighty Great Lakes. Toronto, Ontario’s capital city, is a fun and convenient home base with vibrant multicultural communities and endless adventures, so you may want to arrive early. Then get ready to discover Ontario’s diverse landscapes and rugged beauty on a road trip to one of these charming Canadian towns.

The old mill in Elora, Canada and the Tooth of Time, Ontario

Elora is known as Ontario’s most beautiful village and it’s easy to see why upon arrival. You are welcomed with stunning view of the Elora Mill set against the riverfront and small town charm. The Elora Mill Hotel & Spa has been part of the community for over 175 years and towers above rushing falls and boasts stunning views. Elora is an hour and a half drive from downtown Toronto and located in the township of Centre Wellington along the banks of the Grand and Irvine River. The walkable downtown area has cute boutiques, restaurants, historical buildings, and galleries packed with original artwork. Art lovers can take a studio tour or even participate in a class and make their own masterpiece.

People relax in the water at Elora Quarry Conservation Area near Guelph Ontario Canada on a sunny ... [+] day

Nature lovers will be in their element at the famous Elora Gorge with 80-foot limestone cliffs, cascading waterfalls, and hiking trails like the Riverside trail for spectacular views of the water below. Be on the lookout for my favorite spot inside the Grand River Conservation Authority – Hole in the Rock – a massive rock you can literally walk right through to get to another trail. Or head to Elora Quarry (opens in June), a bucket list Ontario activity with an ‘old swimming hole’, rich forests, and sheer cliffs. Tickets to the Quarry must be purchased in advance online.

Big Tub Lighthouse located in the Bruce Pininsula of Tobermory, Ontario, Canada.

A trip to Tobermory guarantees you beautiful surroundings with sparkling fresh water, a gorgeous shoreline, and endless natural wonders. Located at the Bruce Peninsula’s northernmost point, it’s about a four-hour road trip from downtown Toronto.

Fathom Five National Marine Park, Tobermory, Ontario

Start your adventure at Flowerpot Island in Fathom Five National Marine Park. This beautiful island known for its amazing “flowerpot” rock pillars is accessible only by boat and also has historic caves and a lovely light station. Boat tours leave from Tobermory and if you start at Beachy Cove you can hike over to the flowerpots, explore the area, and have a picnic. Anther fun adventure to add to your Tobermory list is Big Tub Lighthouse. This magnificent 43-foot lighthouse at the entrance to Big Tub Harbour has a rich history and is a fun place to watch the Chi-Cheemaun ferry arriving and departing. When visiting Tobermory you can stay at cozy bed and breakfasts, cottages, hotels, or get back to nature at a wilderness campground. Starting on Victoria Day the Lion’s Head Farmers Market sells local produce on Saturday mornings and has live music at the beach.

"The lighthouse at the entrance to Big Tub Harbor in Tobermory, Ontario.Click on the banner below ... [+] for more lighthouse photos:"

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Boston Pizza restaurant along the Muskoka river in downtown Huntsville, Muskoka region, Ontario, ... [+] Canada, at twilight blue hour.

Beautiful Huntsville is located in the heart of the Muskoka Region , known to locals as cottage country, and a dream warm weather destination. If you are looking for outdoor activities there are many to choose from including picture perfect walking trails, park picnics, and family friendly playgrounds. For beach time and water activities check out one of the many local beaches including Avery Park Beach with access to Trans Canada Trail or Longs Lake Beach that beautifully flows into Three Mile Lake before reaching Lake Rosseau.

Red muskoka chairs at Bruce Peninsula National Park, Tobermory, Canada

Save time to stroll through town exploring galleries and paintings by talented artists. Group of Seven Outdoor Gallery has stunning mural collections showcasing Huntsville, Lake of Bays, and Algonquin Provincial Park. There are over 90 hand painted murals by Canadian artists, with many displayed on buildings around town. History buffs can check out the multiple museums, Tom Thomson Memorial, Historic Brunel Lift Locks, and historic Swing Bridge. Top off your small town visit with a tasty cup of Joe from Row & Roast Coffee Co. on Deerhurst and a walk along the quaint downtown streets shopping for unique treasures.

Canadian Ontario touristic destination place landmark. Red word sign Muskoka on empty road in ... [+] Canada. Summer adventure trip on road. National place for vacation, travel and sightseeing outdoor.

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Tuesday BP: And now, something treacherous

A road trip. A long one.

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The San Francisco Giants are starting to find their bearings, even if it’s not entirely smooth. They’ve scored more than five runs just once in their last 14 games, yet they’re starting to show glimpses of being a competent and, dare I say, perhaps even dangerous baseball team.

But they’re about to get tested. Starting today, the Giants are beginning their longest road trip of the season. Not only do they play 10 consecutive games away from the prettiest ballpark ever built — three each in Boston and Colorado, sandwiching a four-game set in Philly — but they play those 10 games in 10 days ... and then return home for six straight games before finally getting an off day on May 16.

We’ll learn a lot about the Giants, or at least we’ll gain some important info about their place in the standings. Not only is it a treacherous set of games, but when they finally get that beloved off day, they’ll be 45 games into the season. That’s not exactly the time of year to start looking at. magic numbers, but it is deep enough to be looking at the standings regularly.

It’s a testing set of games. The Red Sox have been sneakily good this year, and the Phillies have been excellent, and after those seven games the Giant head to the land of regret, weirdness, and frustration, Coors Field. When they return home, they have to host a team they’re in direct competition for the postseason with, the Cincinnati Reds . And the final boss they get to face, as a reward for making it to the end of 16 games in 16 days? The Los Angeles Dodgers , naturally.

Personally? I think they win 17 of these next 16 games. Keep the faith.

What time do the Giants play today?

The Giants and Red Sox play a good old fashioned game of baseball at 4:10 p.m. PT today.

More From McCovey Chronicles

• Thursday BP: Breakfast Baseball! - 5/2 Gamethread - Giants @ Red Sox
• Giants lose to Red Sox again, 6-2
• 5/1 Gamethread: Giants @ Red Sox
• Giants likely to have an opinion about the movie Challengers, ranked
• The Do’s and Don’ts of judging the Giants one month into the season
• Wednesday BP: Not all heroes wear capes

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