road trip new england states

The Flexible New England Road Trip Itinerary You Need in 2024 ❤️

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

READ NEXT   18 Magical New England Christmas Towns that are Straight Out of a Hallmark Movie (Updated 2023)

Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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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.

Drink water from ANYWHERE. The Grayl Geopress is the worlds leading filtered water bottle protecting you from all manner of waterborne nasties.

Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

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!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

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

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

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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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Unforgettable New England road trip

• Post last modified: March 18, 2024

Planning a road trip through New England ? Get to the heart of the United States ‘ most idyllic corner with this ultimate itinerary, where soothing nature, delightful towns and proud tradition abound. Buckle up — here are all the gems you don’t want to miss.

Disclosure: All listings are independently selected. If you buy something through our links, we may earn an affiliate commission. Learn more ›

New England route

• Start: Boston
• North Conway
• North Adams
• Stockbridge
• Finish: Boston

Begin with a salty trip up along New England’s coast, where Portland, Camden and Acadia NP are highlights. While Interstate 95 is usually quicker, consider sticking to the parallel, more scenic Route 1.

Then, the character of the itinerary changes dramatically. Head west to see the White Mountains, Green Mountains and Berkshires, with the lofty scenery peaking along the iconic Kancamagus Highway.

Back on the coast, explore Mystic, Newport and Cape Cod. Home to Cape Cod National Seashore, Cape Cod provides some of America’s best beaches, making for the perfect finish to your epic drive.

Isn’t Boston the optimal starting point for you? Feel free to start the loop at the location that suits you best.

• Total distance: 1,213 mi / 1,952 km
• Total driving time: 25 h

1. Boston, MA

Massachusetts ‘ largest city, Boston is certainly a convenient place to begin a Northeast road trip. There’s the well-connected Logan Airport and an array of rental car companies to choose from.

But — most of all — Boston is a fun city to explore before you get deeper into the New England itinerary.

If one thing to do in Boston is mandatory, it’s the Freedom Trail . Walking the 2.5-mile (4 km) path, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a memorable experience before heading north — baseball fan or not.

More info: Where to stay in Boston

2. Portland, ME

• Driving distance:  112 mi / 180 km
• Driving time:  2 h

On Maine’s southern coast, Portland offers a lot for anyone looking for a good time.

In particular, the historic Old Port — characterized by cobblestone streets, red-brick buildings, quaint wharves and fishing piers — is the crown jewel. While its facades remind you of past glory days, the district is a modern-day gold mine with eclectic boutiques, watering holes and restaurants.

Capturing at least one of the many lighthouses in the Portland area is also a must, and especially one stands out: Portland Head Light was completed in 1791, making it Maine’s oldest lighthouse.

3. Camden, ME

• Driving distance:  81 mi / 130 km
• Driving time:  1 h 45 min

Countless scenic towns hug Route 1. Camden may be the most picturesque of them all.

Picture a small town lacing an Atlantic cove (Penobscot Bay) with steep slopes (Camden Hills). If you’re short on time, stretch your legs while you browse the stores on the timeless Main Street or sit down in the Camden Amphitheater, a small oasis facing the harbor.

With more time, hike into the rising Camden Hills State Park. But if you don’t want to work for it, you can also drive up to the top of Mount Battie, brilliantly capturing the scenery.

4. Acadia NP, ME

• Driving distance:  77 mi / 124 km

Welcome to the only national park in New England, Acadia. Calling Mount Desert Island home, it encompasses some of the Atlantic’s most untamed coastline — this is one of the most beautiful places in the US .

Although you find awe-inspiring nature all over the island, the eastern half of Mount Desert Island holds most of the park’s big-ticket spots.

An unrivaled eastern highlight is Cadillac Mountain. The views of Acadia are just spectacular from Cadillac Mountain’s summit, both the tallest point of the park and the USA’s eastern seaboard.

Cadillac Mountain peaks at sunrise and sunset but is a beautiful experience throughout the day.

On Mount Desert Island’s quieter western half, another photogenic spot not to miss is Bass Harbor Head Lighthouse. Built in 1858 on the island’s southern tip, it’s not quite as old as Portland Head Light — but no less pretty.

More info: Where to stay near Acadia NP

5. North Conway, NH (White Mountains)

• Driving distance:  212 mi / 341 km
• Driving time:  4 h 15 min

New Hampshire ‘s White Mountains region is filled with great things to do, boasting both stunning natural beauty and cozy towns to relax in.

A shining example of the latter, North Conway is the perfect White Mountains gateway when you come from the east. From here, you effortlessly reach many highlights in the dense White Mountain National Forest.

Within a few miles, Diana’s Baths Cascade — a series of waterfalls dropping 75 feet (23 m) — is a spellbinding place. Another nearby stop is Cathedral Ledge Lookout, offering White Mountains vistas destined for Instagram fame.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway — one of New England’s most scenic drives — is a jaw-dropping experience. As it runs from Conway to Lincoln, it also takes you right to your next base on the itinerary.

6. Lincoln, NH (White Mountains)

• Driving distance:  41 mi / 66 km
• Driving time:  1 h

Ready for more gorgeous terrain? At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest.

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess first had trouble convincing her family about the discovery. It just sounded too magical to be true — but the rest is history.

Today, the Flume is a highlight in Franconia Notch State Park. You find a good variety of hiking trails in Franconia, letting you explore the White Mountains and its dense forests, stunning lakes and majestic peaks further.

7. Stowe, VT (Green Mountains)

• Driving distance:  85 mi / 137 km

A Vermont village with a postcard-worthy downtown area, Stowe sits at the foot of the Green Mountains.

Just strolling down Main Street in Stowe is an appreciated thing to do. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far from fresh air and beautiful views. Stowe Recreation Path provides a convenient way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. Be careful so you don’t get a brain freeze at the original Ben & Jerry’s ice cream factory in Waterbury.

Extra stop: Consider stopping in Burlington, VT, a fun city on the shore of Lake Champlain. Because it’s just 36 miles (58 km) between Stowe and Burlington, you can easily include both on your New England itinerary.

8. North Adams, MA (The Berkshires)

• Driving distance:  159 mi / 256 km
• Driving time:  3 h 15 min

It’s the rolling hills and captivating culture that define The Berkshires region. Marking its northern end, where Vermont meets Massachusetts, North Adams is a great place to start exploring.

Be inspired by evocative galleries and performances at the Massachusetts Museum of Contemporary Art, set on the Hoosic River in downtown North Adams.

Or, simply cruise onwards, letting the peaceful landscape wash over you. North Adams sits along the Mohawk Trail, one of New England’s most scenic drives, finishing in nearby Williamstown.

9. Stockbridge, MA (The Berkshires)

• Driving distance:  35 mi / 56 km

America’s favorite illustrator, Norman Rockwell called Stockbridge home for 25 years. Here, with hundreds of original works, the Norman Rockwell Museum honors and showcases his legacy.

Before Rockwell, the writer Edith Wharton lived in the Berkshires, too. Visit her historic Lenox residence, the expansive Mount Home (maybe on your way from North Adams to Stockbridge), to learn and absorb the idyllic setting.

These are cultural treasures, but don’t forget that what makes the Berkshires outstanding is the mix of culture and nature.

For hiking, a beautiful spot is October Mountain State Forest . At roughly 16,500 acres, it’s Massachusetts’ largest state forest, offering both easy and strenuous trails.

More info: Where to stay in The Berkshires

10. Mystic, CT

• Driving distance:  127 mi / 204 km
• Driving time:  2 h 15 min

On the Connecticut coast, the village of Mystic peacefully sits. Get ready to discover its proud history as a waterside community and center for shipbuilding.

By the Mystic River, Mystic Seaport Museum is one of the USA’s leading maritime museums, preserving an array of seafaring artifacts. Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws.

Compact Historic Downtown Mystic has you covered for authentic shopping, diverse eateries and charming waterfront views. Especially pay attention to the Mystic River Bascule Bridge, a still-in-use drawbridge — nowadays a rare sight.

Extra stop: An alternative to Mystic or an additional stop on the itinerary is New Haven, CT, the home to the famous Yale University.

11. Newport, RI

• Driving distance:  48 mi / 77 km

The shore of Rhode Island is an essential ingredient on your New England road trip itinerary. On Aquidneck Island, Newport is an old colonial city with attractions covering a wide spectrum.

Walking the renowned Newport Cliff Walk, 3.5 miles (5.6 km) long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and fresh salty air.

As a bonus, eye-popping mansions frame the trail.

For the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are also impressive.

More info: Accommodation in Newport, RI

12. Cape Cod, MA

• Driving distance:  120 mi / 193 km
• Driving time:  2 h 30 min

These 120 miles (193 km) take you all the way to the northern tip of Cape Cod , a peninsula separated from the mainland by the Cape Cod Canal since 1914. Be sure to make plenty of stops along the way.

Cape Cod Rail Trail, excellent for walking or biking, presents a healthy way to sightsee. Paved and extending for 25 miles (40 km) from South Yarmouth to Wellfleet, it follows the 19th-century rail lines that used to carry tourists to Cape Cod.

At the trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly never-ending beach — seals thrive in the waters here — or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach, as far north as you get, is a phenomenal beach with huge sand dunes. On a sunny day, you might ask yourself: Is this Massachusetts or Florida?

More info: Best areas in Cape Cod

13. Boston, MA

• Driving distance:  116 mi / 187 km

It’s time to round off your unforgettable New England road trip. The last leg is the drive back to where the adventure started, Boston. From the isolated Provincetown, it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself elsewhere on Cape Cod.

Where to stay when you road trip through New England

New England takes pride in its atmospheric, often historic inns. Consider making your road trip even better by booking one of our favorite places to stay on Cape Cod.

Appreciate the English Country style at the Old Harbor Inn , a luxurious bed and breakfast set in Chatham. Each of the twelve rooms is unique and the location spot-on for day trips across Cape Cod.

Or, stretch your budget by staying at the Breakwater Hotel , slightly outside Provincetown, at Cape Cod’s northern tip. Drive 5 minutes or walk 30 minutes to get to Provincetown’s heart.

New England itineraries with days

For the full New England road trip, we recommend allowing at least 3 weeks. If you have less time, it’s a good idea to break up the itinerary to focus on your favorite parts.

Ultimate itinerary (3 weeks)

• Day 1-3: Boston (2 nights)
• Day 3-5: Portland (2 nights)
• Day 5-8: Acadia NP (3 nights)
• Day 8-10: North Conway (2 nights)
• Day 10-12: Lincoln (2 nights)
• Day 12-14: Stowe (2 nights)
• Day 14-15: The Berkshires (1 night)
• Day 15-16: Mystic (1 night)
• Day 16-18: Newport (2 nights)
• Day 18-21: Cape Cod (3 nights)

2 week road trip (Atlantic coast)

• Day 1-2: Mystic (1 night)
• Day 2-4: Newport (2 nights)
• Day 4-7: Cape Cod (3 nights)
• Day 7-9: Boston (2 nights)
• Day 9-11: Portland (2 nights)
• Day 11-14: Acadia NP (3 nights)

7 day road trip (Mountain trip)

• Day 1-4: White Mountains (3 nights)
• Day 4-6: Green Mountains (2 nights)
• Day 6-7: The Berkshires (1 night)

New England road trip FAQ

This ultimate New England road trip is 1,213 miles (1,952 km) long, taking 25 hours excluding the time you need for the stops along the way.

The journey includes six states: Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

The main stops on the itinerary are Boston, Portland, Acadia NP, White Mountains, Green Mountains, The Berkshires, Mystic, Newport and Cape Cod.

For the full loop, we recommend allowing 3 weeks or more. But you can break the itinerary up and enjoy a shorter journey, too, for example, focusing on the coast or the mountains.

With 7 days, it’s as good idea to concentrate on a certain area. To see both a lively city and New England’s timeless coastal environment, a popular combo is Boston and Cape Cod.

More New England guides

• Cape Cod vacation guide
• Where to stay in Cape Cod
• Lodging near Acadia NP
• New England bucket list

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Road-Tripping New England: My Suggested Itinerary

I’ve said it before and I’ll say it again: The United States is made for road trips . With its bustling cities, rugged national parks, and delicious eats, the sheer size and diversity of this country never cease to amaze me.

I’ve road-tripped the USA five times, spending a cumulative year exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.

One region in particular that I love to drive around is New England.

Having grown up in Boston and gone to college in Western Massachusetts, I’ve spent a lot of my life in this part of the country. I’ve also road tripped around the region.

During a recent summer, I explored parts of Maine , Cape Cod, and upstate New York that I had never seen before.

And yeah, I’m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.

If you’re thinking of visiting, here’s a suggested road trip around New England to help you get a feel for the region:

Table of Contents

Days 1-3: Boston, MA

Days 4-5: portland, me, days 6-8: bar harbor, me, day 9: bangor, me, days 10-12: moosehead lake, me, days 13-14: mount washington, nh, days 15-17: burlington, vt, days 18-19: green mountain national forest, vt, days 20-22: the berkshires, ma, day 23: amherst, ma, day 24: back to boston, bonus destination: cape cod, ma.

These are some of my favorite things to do in Boston:

• Walk the Freedom Trail – This 2.5-mile (4km) route takes you through colonial Boston. Starting in the Boston Common and winding past Faneuil Hall, the Old State House, and Bunker Hill, this historical walk teaches you about life in colonial and revolutionary times. If you’d prefer a guided tour, Boston History Company runs daily tours for $31 USD that offer excellent insight into the area’s important past.
• See the Museum of Fine Arts – This museum has over 450,000 pieces of fine art, from the pre-Columbian era to Italian Impressionism. It’s one of the best collections in the country. Admission is $27 USD.
• Visit Bunker Hill Monument – The Battle of Bunker Hill in 1775 was one of the first major clashes of the Revolutionary War. While the redcoats won, the Americans wore British forces down more than was expected. The monument stands 221 feet tall; you can climb to the top to enjoy the view (it’s the best view of Boston).
• Lounge in Boston Common – This is the oldest city park in the US, dating to 1634. It was once used as communal pasture land by Puritan settlers (they also executed some “witches” here as well). Today, it’s a great place to relax, people-watch, and picnic.
• Visit Harvard – Harvard University is the first and oldest university in the country (founded in 1636, far predating the United States). The campus offers free one-hour tours through the grounds and buildings. Afterward, grab a coffee and people-watch in the alternative and artsy Harvard Square.
• Catch a game at Fenway Park – This is one of the oldest baseball parks in the country (it opened in 1912). Bostonians are die-hard Sox fans, so even if you don’t like baseball, go for the cultural experience. Tickets start around $29 USD for standing room or bleacher seats, and $39 USD for the grandstand. Guided tours of the stadium are offered year-round as well. There are various tour options, but the standard guided tour lasts 90 minutes and costs $25 USD per person.

For more suggestions on what to do in the city (and there’s plenty), check out my free guide to Boston .

Where to Stay

• HI Boston – This is my favorite hostel in the city. It’s clean, spacious, and social, and the staff are super friendly and helpful.

For more suggestions, here is my list of the best places to stay in Boston .  

• Visit Peaks Island – This small island is home to around a thousand people. Located just 20 minutes off the coast, it’s a laid-back place to eat, lounge, and check out the quaint shops. There’s also a small World War II museum here, as well as a neat umbrella cover museum (it’s more interesting than it sounds!).
• Try a Holy Donut – Holy Donuts are made from Maine potatoes (which sounds weird, but they are incredibly tasty), so they are at least somewhat healthier than your standard donut. There’s always a line, so try to get there early!
• See the lighthouses – There are several historic lighthouses worth seeing nearby, including the Portland Breakwater (which was designed to look like a Greek monument), Spring Point Ledge (which was built in 1897 and is open for tours on weekends), and Portland Head Light (which was built in 1791).
• Wander Victoria Mansion – This ornate mansion-turned-museum, built in 1860 and declared a National Historic Landmark in 1971, boasts a brownstone exterior and elaborate interior furnishings. It’s incredibly lavish, shedding light on what life was like for the well-to-do in the late 19th century. Admission is $19.25 USD.

While you’re in Portland, be sure to check out some of the city’s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.

• Black Elephant Hostel – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping.

Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.

Here are some things to see and do in and near Bar Harbor:

• Explore Acadia National Park – This gorgeous national park encompasses forests, lakes, and mountains, and covers a large swath of the Atlantic coastline. It’s incredibly popular in the summer for hiking, biking, camping, kayaking, and more. You could easily spend a couple of days just exploring the park. A 7-day vehicle pass is $35 USD and camping starts at $22 USD per night.
• Visit Abbe Museum – This museum showcases the area’s indigenous history and culture. It’s very informative and sheds important light on a history often overlooked. It’s part of the Smithsonian, so you know it’s going to be good! Admission is $10 USD.

Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie’s (delicious food all around).

• Bar Harbor Manor – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace.

My favorite places to eat are Fiddleheads (delicious food all around) and Judy’s (best diner breakfast). For a drink, head to Mason’s Brewing.

Where to Stay Bangor is a small town, so you’ll want to compare prices on Booking.com and Airbnb to see what best suits your budget.  

Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer.

For dinner or drinks, head to the Stress Free Moose Pub in Greenville.

• Leisure Life – This accommodation is basic, but it’s in a great location (in Greenville), and the staff are super helpful.

Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).

Where to Stay You can stay in nearby Gorham or Littleton. Check Booking.com and Airbnb to see what best suits your budget.  

Some of my favorite things to do here are the following:

• Wander Church Street – This pedestrian-only thoroughfare is the heart of the city. Café-hop, browse the bookstores and other shops, and take in the slow pace of life.
• Get out on the water – Spend some time out on the water and soak up the sun. Boat rentals, cruises, paddle boarding, kayaking — you can do it all here. There are also several beaches you can lounge on, with North Beach being the most popular.
• Visit Ben & Jerry’s – This is where the global ice cream brand originated. If you have more time, you can visit the nearby factory in Waterbury and see the “ice cream graveyard,” where Ben & Jerry’s commemorates its obsolete flavors.
• Indulge in craft beer – Burlington is a craft beer mecca, home to over a dozen breweries. Go bar- or brewery-hopping to taste the best the city has to offer. Local favorites include Foam Brewers, Zero Gravity, Fiddlehead Brewing Company, and the Burlington Beer Company.

Where to Stay There are no hostels here, so compare prices on Booking.com and Airbnb to see what best suits your budget.  

Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.

Since it’s a national forest, camping here is free (unless signs advise otherwise).  

Here are some things to see and do:

• Hike Mount Greylock – Standing 3,491 feet tall and located in a state park encompassing over 12,000 acres, Mount Greylock is the highest peak in Massachusetts. There are several trails that lead to the summit (including a portion of the Appalachian Trail). The hike takes around 90 minutes, and the views from the top are absolutely breathtaking — you can see for miles!
• Visit the Norman Rockwell Museum – Norman Rockwell, the prolific American painter and illustrator, spent much of his life in Stockbridge. A museum was established there to showcase his life and works, highlighting the evolution and impact of his art. Admission is $20 USD.
• Explore Natural Bridge State Park – Located in North Adams, this park is home to a natural bridge of white marble (which is over 550 million years old) as well as an old marble quarry. There’s an easy trail around the bridge and quarry, and plenty of relaxing fields and meadows to picnic in. Parking is $20 USD for out-of-state residents.

Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson’s life. There are often events and poetry readings here, so check the website to see what’s on during your visit. Guided tours last 60 minutes and cost $16 USD.

As for food, Antonio’s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I’m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.

It’s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston!  

Here are some things to see and do during your stay:

• Go whale watching – From April to October, you can see finback, minke, and humpback whales, as well as dolphins and seals. Tours cost around $67 USD.
• Hike or bike the National Seashore – Created in 1961 by JFK, this park spans over 43,000 acres. There are 11 hiking trails, as well as half a dozen cycling trials. All of them are well marked so it’s an easy way to stretch your legs and take in the beautiful landscape.
• Visit some lighthouses – There are dozens of picturesque lighthouses around Cape Cod, some of which are open to the public. Don’t miss Nauset, Nobska, and Highland lighthouses.

New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I’m proud to have grown up in this region and encourage you to explore my backyard!

Book Your Trip to the United States: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe, so you always know no stone is being left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as it has the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it, as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those 70 and over)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road, and I’m sure they will do the same for you.

Need an Affordable RV for Your Road Trip? RVshare lets you rent RVs from private individuals all around the country, saving you tons of money in the process. It’s like Airbnb for RVs.

Want More Information on the United States? Be sure to visit our robust destination guide on the USA for even more planning tips!

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The ultimate 10-day new england road trip itinerary.

New England, with its quaint villages, idyllic landscapes, rich history, and mouthwatering culinary experiences, is a treasure chest of delights waiting to be unlocked. From the rugged beauty of the Maine coastline to the vibrant, artistic vibe of Providence, this is a region that never fails to enchant.

If you’re up for the crisp smell of the ocean mingled with pine trees, the rustic charm of cobblestone streets lined with centuries-old houses, and the taste of the most succulent seafood freshly plucked from the sea, then you have to start planning your New England road trip!

» You might be interested in a shorter version with this Boston to Bar Harbor road trip itinerary.

» Looking for more travel inspiration in the United States ? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit . Here are a few more fabulous U.S. Cities to visit .

The only real problem is deciding what to do and see and how to fit everything into ten days. Lucky for you, we’ve done this road trip multiple times and have passed through these states on a number of different trips, so we have the knowledge to help you plan an amazing time on one of the best road trips in the United States .

Table of Contents

Essential New England Road Trip Info

Comprising six states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont -there’s a lot of ground to cover during a New England driving tour. It’s not a small amount of driving, despite how close together many of these states are. So if you’re planning to embark on this road trip, keep this in mind.

You can either fly into a set starting point – we recommend Boston – or you can drive in from where ever you’re located in the United States. In any case, you’re going to need a car – either your own or a rental car . If you’re renting, we suggest going through Discover Cars to get the best deals from all the top car rental companies in one place.

How to Get to New England

If traveling from Europe or another destination outside the States, you’ll fly into Boston for this itinerary. Considering the region’s most popular international airport, Boston Logan International Airport (BOS) is where your trip will start and end.

If Boston doesn’t work for you, you can also fly into New York City , Philadelphia, or even Washington, DC. It will just take you a little longer to drive to the start point of this road trip, but there is plenty to see along the way.

When Should You Do on a New England Trip?

Unless you’re a winter die-hard, the best time to visit New England is undoubtedly during the fall, from September to December, or spring, from March to June. 

Fall is when the landscape takes on a magical element with changing colors in every shade of gold, orange, red, and brown imaginable. Aside from that, the crisp, clear fall air and the New England sun bursting through the morning mists are second to none, making it one of the best fall destinations in the USA .

If you can’t swing a fall road trip, the second best time is during spring. This is before the heat of the summer really sets in, so temperatures will be mild and enjoyable. I would definitely not go in summer, if at all possible, because it can get really hot and humid.

New England Road Trip Itinerary

Are you ready to buckle up and join me on a 10-day road trip across these six picturesque states? I’m thrilled to share this thoroughly curated itinerary that will ensure you make the most out of this journey, exploring the hidden gems as well as the must-see spots.

Whether you’re a history buff, a foodie, a nature enthusiast, or simply someone who enjoys the thrill of exploring new places, this 10-day New England road trip has something for everyone. So pack your bags, put on your favorite road trip playlist, and let’s hit the road.

Boston, Massachusetts (Day 1)

After arriving in Boston, Massachusetts , you can jump directly into the first day of your trip by visiting Boston. Drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, you’ll find a million historical things to see alongside plenty of sports bars to grab a beer in at the end of your day. While there’s no way to see the best of Boston in one day, we suggest you include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem, Massachusetts & Portland, Maine (Day 2)

Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you’ll drive for about 40 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. If you’re visiting during October, prepare for an overload of everything spooky. No matter when you’re in town, here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

When you’re done exploring spooky Salem, jump back on Route 127. After about an hour and forty minutes, you’ll reach Portland, Maine. 

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews and distilleries. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

• Visit Fort Williams Park and the Portland Head Light
• Tackle a brewery tour of Portland to some local craft breweries
• Shop the local boutiques and specialty shops of Old Port
• Grab a sunset view along the Eastern Promenade
• Eat lobster rolls at Luke’s Lobster on the pier

Tours to look out for while you’re in Portland:

• Old Port Culinary Walking Tour
• Cusco Bay Sea Kayaking Tour
• A Walk Through Time Tour in Portland 

Where to stay: Portland Regency Hotel & Spa

Bar Harbor & Acadia National Park, Maine (Day 3)

Your third day along this New England trip requires an early start and a three-hour drive, but the rewards are totally worth it. Driving from Portland to Bar Harbor, the beach town gateway to Acadia National Park, prepare for some out-of-this-world scenery.

Along the route, you’ll pass through a few towns worth a stop. The first is Bristol, where you can spend a minute or two at the Pemaquid Point Lighthouse , then stop at the Camden Hills State Park in Camden to see the view from the top of Mt. Battie.

After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park. You need a U.S. Park Pass to get in. If you’re going to be visiting more than one park in the year, you should definitely consider getting the America the Beautiful annual pass, which is just $79.99 from REI.

On Maine’s largest island, Mount Desert Island, the 47,000-acre Acadia National Park has dramatic mountains, picturesque lakes, and endless miles of hiking trails. It’s one of the biggest draws to this part of the U.S.

The top three things to add to your Acadia itinerary include:

• Hiking to the summit of Cadillac Mountain (vehicle reservations are required for Cadillac Summit Road from May 25 through Oct 22). Book online.
• Kayaking on Swan Lake
• Biking or driving the Park Loop Road. The Park Loop Road can be very crowded. Have a backup plan if the area you wish to visit is full.

Where to stay: Bar Harbor Inn

White Mountain National Forest, New Hampshire (Day 4)

While you technically did venture into stunning New Hampshire earlier in your road trip, day four is all about heading to and roaming around one of the state’s top attractions. The drive to get there is another 3 hours 30 min drive, so get up early!

Topping most driving tours of New England, especially those focused on New Hampshire, White Mountain National Forest is a beautiful collection of natural landscapes. The best thing about the National Forest is that there are many unique activities to indulge in regardless of what time of year you’re visiting.

• In springtime, thanks to warmer weather and melting snow, the forest delivers the perfect setting for hiking and camping.
• During the summer, you can fill your day by hiking, fishing, or canoeing.
• When fall arrives, you should set out to drive New Hampshire’s scenic Kancamagus Highway.
• Wintertime brings with it a lot of snow-capped mountains fit for winter sports enthusiasts at numerous ski resorts.

Where to stay: The Inn at Thornhill & Spa

Stowe, Vermont (Day 5)

Once you’ve said farewell to New Hampshire, it’s time to head to NEK or the North-East Kingdom of Vermont. It’s a 1 hour 30 minute drive. Known for its spectacular green mountains, eye-catching lakes, and charming small farms, the state is a buzzworthy must-visit.

On the way to Stowe, you’ll stop in Waterbury for a genuine pilgrimage to the ice cream empire and the original store of Ben & Jerry’s.

Next up is a short 20-minute drive north to the ski resort town of Stowe. This world-famous ski destination showcases an authentic small-town charm, a lively main street, and some iconic steepled churches.

Be sure to check out some of Stowe’s one-of-a-kind local favorites, such as Laughing Moon Chocolates, Shaw’s General Store, and The Deep End (the hippest pizza place in the state). Other options here include:

• Skiing at the Trapp Family Lodge
• Hiking in Green Mountain National Forest
• Heading on a scenic drive on Mountain Road

Where to stay: The Lodge at Spruce Peak

Litchfield & Mystic, Connecticut (Day 6)

Another early start on day six, you’ll drive down the Route 100 Scenic Byway, Vermont’s longest highway, through Wilmington, across the border into Connecticut. First stop of the day? Litchfield; a charming New England town brimming with local history. It’s a 4-hour drive to get there.

Founded in 1719, today, the town is a popular tourist destination known for its antique shops, numerous art galleries, and historic homes.

Delving further into Connecticut, you’ll head east to the town of Mystic. This historic seaport sits snuggly on the Mystic River and is most famous for its maritime heritage and the setting of the 1988 film Mystic Pizza .

Here are some highlights in Mystic:

• Visit the Mystic Seaport Museum , one of the largest in the world
• Explore early colonial farm life at the Denison Homestead
• Dive into some aquatic adventures at the Mystic Aquarium
• Hike a trail or two in Bluff Point State Park

Where to stay: Hilton Mystic

Newport, Rhode Island (Day 7)

Continuing the coastal New England road trip, the next stop along your journey is in Rhode Island. Although it’s the smallest state in the US, it is home to some of the country’s most historic towns, most notably Newport. This is only an hour drive.

This seaside town, once a summer retreat for America’s most wealthy families, boasts breathtakingly stunning mansions built during the Gilded Age and is quite the sight to behold. Beyond that, you’ll find pristine beaches and some of the best seafood in the country here.

When you’re planning your day in Newport, be sure to include these must-do activities:

• Stroll along Cliff Walk, a coastal 3.5-mile pathway hugging the Atlantic Ocean
• Indulge in some retail therapy along Bellevue Avenue and Thames Street
• Head out wine tasting at Greenvale Vineyards
• Tour the famous Newport Mansions
• Explore Bowen’s Wharf or take a boat cruise from Long Wharf
• Relax on the sands of Easton Beach

Where to stay: Newport Marriott

Cape Cod (Day 8)

Next up, and after an entire week on the road, it’s time for some rest and relaxation on the flexed arm of Massachusetts, in Cape Cod, a 1-hour 30-minute drive. Sitting on a peninsula in the state’s southeastern region, Cape Cod has long been a summer destination for the rich and famous.

Now if you’ve ever wondered why New England beach vacations are so popular, the almost 560 miles of coastline that encircle Cape Cod provide a clear answer. Yes, there are many great towns here worthy of a stay, but for this road trip, you’ll spend the day and night in Sandwich.

The official oldest English settlement in Cape Cod, Sandwich, dates back to 1639 and stuns with calm beachfront, quaint eateries, and a vibrant historic district. Fill your day in Sandwich with some of these standouts:

• Breakfast at Cafe Riverview
• Stroll along East Sandwich Beach
• Visit Sandwich Boardwalk
• Explore the Sandwich Historic District
• Indulge in the best lobster in town at Mattakeese Wharf

Where to stay: Sandwich Lodge & Resort

Plymouth, Massachusetts (Day 9)

What would an itinerary for a New England road trip be without a stop in Plymouth? That’s why your second-to-last day in the area is all about exploring the town that dates back to 1620. It’s a 30-minute drive from Cape Cod.

Today this quintessential New England town is most known as the site where the very first Thanksgiving took place and is home to Plymouth Rock. Steeped in history, this is where the Pilgrims first landed way back when.

With all that history, here are a few top spots you should visit while in Plymouth:

• Explore Plimoth Patuxent , a living history museum with a replica of the Mayflower ship
• Grab a few snapshots at Plymouth Rock and delve into the Pilgrim Hall Museum
• Roam around Plymouth’s historic downtown harbor area, home to several notable buildings such as the Plymouth Courthouse
• Cap off your day with a stroll along Plymouth’s famously historic waterfront and catch the sunset over Cape Cod

Where to stay: Thomas Sea Suites at Harbourtown

Boston, Massachusetts (Day 10)

Finally ending your epic 10-day New England road trip, you’re back in Boston . Luckily the drive from Plymouth to Boston is only 45 minutes to an hour, so you can start the day a bit later and still be back in Beantown with some time to spare for any extra activities.

We’d recommend fitting anything you didn’t have time for on day one into your final day. If you’ve got a few extra hours, here are some other Boston highlights to add:

• For history lovers, pay a visit to the USS Constitution Museum or the Paul Revere House
• Art lovers should definitely head to the Isabella Stewart Gardner Museum and the Museum of Fine Arts
• Sports fanatics should take a one-hour tour of Fenway Park or catch a Boston Red Sox game ( check their calendar here )
• For food lovers, be sure to check out our foodie guide to Boston .

Where to stay: Hyatt Centric Faneuil Hall Boston

Wrapping Up Your Road Trip Through New England

There you have it – the best road trip through New England you could possibly do in ten days. Although numerous other attractions and standout activities can be included on any trip, this New England trip itinerary features the best of the best.

Of course, you can play around with other vacation ideas in New England or discover hidden travel tips heading off-the-beaten-path. Now all you have to do is decide when to go and prepare for some exciting road-tripping in New England.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

YOU MIGHT ALSO LIKE

8 Foodie Things to Do in Boston Massachusetts

17 Awesome Places to Visit in the United States

13 Best Cities to Visit in the United States

5 Top Historic Cities in the U.S.

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Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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10-Day New England Road Trip Itinerary

Whether you’re looking for a summertime family vacation, colorful fall foliage, or a romantic snowy winter getaway, the northeast corner of America makes for an ideal destination.

Being that most Americans only get two weeks of vacation time a year, we’ve planned this 10-day New England road trip strategically.

This itinerary includes the best places to visit in New England. You’ll get to experience everything from quaint villages to bustling cities and national parks, of course. Plus, there will be plenty of breathtaking scenery along the way!

So, grab your camera and get ready. It’s time to road trip New England and discover what this corner of America has to offer!

Where is New England?

New England is located in the northeastern part of the United States. It’s made up of six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. The region is known for its rocky coastline, autumn foliage, and cold, snowy winters.

New England trip planning tips

Even before you begin planning your New England road trip, there’s one absolutely essential thing you need to know: Hotels fill up very quickly.

To avoid disappointment, be sure to book all your accommodation as soon as you know your travel dates! We’re not kidding. People book months in advance to secure a place to stay.

Same with New England tours. They are very popular , especially in the fall and winter months. And it’s not just for road trips. Bostonians book these spots as weekend getaways as well.

If you plan to rent a car, do it ahead of time. Not only does that guarantee you the lowest rates, they’ll reserve the type of car you prefer.

Now that you have everything reserved, let’s set out on your road trip!

ⓘ PRO TIP: If you’re a comparison shopper, check out Discover Cars . We use them ourselves because they provide a hassle-free experience and offer fantastic prices.

Day 1: Salem, Massachusetts and Portland, Maine

Most people plan their driving vacations from Boston because it has the largest airport in New England. Arrive at Boston Logan International Airport in the morning, pick up your car, and head out of town.

Your first stop will be Salem, where you’ll explore the city’s infamous witch history. Start at the Salem Witch Museum to learn all about the famous Salem witch trials of 1692. Then, visit the Salem Witch Trials Memorial near the water, and snap a selfie in front of the House of the Seven Gables, made famous by author Nathaniel Hawthorne.

If you prefer, you can book a 90-minute Witchcraft Trials Walk with a licensed and professional guide who will bring Salem’s history to life.

Pop in at Red’s Sandwich Shop or Deli House for lunch. You can either dine in or order takeout and eat on the road, as you wish.

Now, continue your drive north to Portland, Maine’s largest city. This lively city is full of great restaurants, bars, and shops, as well as plenty of art galleries and museums.

Spend your afternoon strolling along the cobblestone streets of Portland’s Waterfront Old Port Historic District, touring the Portland Museum of Art, or visiting Victoria Mansion, a beautifully preserved 19th-century home.

End your day with lighthouse cruise on Casco Bay and a foodie walking tour  through the streets of the charming Old Port, where you’ll learn about local history, foods & drinks.

Where to stay in Portland Maine

• Budget: The Black Elephant Hostel has air-conditioned accommodations, a shared kitchen, and a shared lounge, along with free WiFi throughout the property. Some rooms at the property feature a balcony with a garden view.
• Mid-range: Hampton Inn Portland Downtown Waterfront   offers free airport and local shuttles, an indoor heated pool, and a fitness center.
• Luxury: The Francis , a historic landmark, is located in Portland’s Bramhall neighborhood, near the Art District. Museums, galleries, theaters, skating rinks, craft breweries, and boutiques are within a 0.9 mi radius of the property.

Day 2: Acadia National Park Maine

It may look quite far on the map, but in reality, it only takes about three hours to drive from Portland to Acadia National Park. So get an early start and hit the road!

Acadia National Park is one of the most popular tourist destinations in Maine, and for good reason. Located on Mount Desert Island, Maine’s largest island, this 47,000-acre park is home to towering mountains, pristine lakes, and miles of hiking trails.

Here, rocks erode into the ocean and iconic lighthouses stand high above them. Wildlife can be seen both in the water and on land, and there are numerous hiking trails to explore.

Today’s first stop will be Bar Harbor, a beach town that’s also the gateway to Acadia National Park. You can take a walking tour through Bar Harbor before checking into your hotel, and then head to the park after lunch.

There are plenty of things to do in Acadia National Park, but some of the most popular activities include hiking to the top of Cadillac Mountain (the highest point on the U.S. Atlantic coast), kayaking in Swan Lake, and biking or driving the Park Loop Road.

To end your day, enjoy a dinner of ocean-fresh fish in one of the many excellent restaurants on the island .

ⓘ TIP: This inexpensive Acadia National Park Self-Guided Driving Tour is a personal guide, audio tour, and map all rolled into one. Simply download the app and connect to the car speakers; it’s yours to keep. Less than $15 for a guided driving tour of Bar Harbor and Acadia National Park? Yes please!

Where to stay near Acadia National Park (Bar Harbor)

• Budget: Various campgrounds are available in the area.
• Mid-range: Acadia Inn is a family-friendly hotel 1.1 miles from the center of town. The hotel offers a complimentary breakfast buffet each morning, free wi-fi, air conditioning, a hot tub and outdoor pool, and an on-site trail that accesses the park. 
• Luxury: Chiltern Inn Featuring an indoor pool and sauna, this Bar Harbor bed and breakfast is located 1.6 mi from Acadia National Park. Rooms at the Chiltern Inn offer a wood-burning fireplace, free Wi-Fi, and a private bath.

Day 3: White Mountain National Forest, New Hampshire

After spending two days in Maine, it’s time to head into New Hampshire. You’ll spend the morning on the drive from Acadia National Park to White Mountain National Forest, and the vistas are so beautiful you’ll thoroughly enjoy the long drive!

White Mountain National Forest tops most New Hampshire itineraries, with unnumerable towering mountains, pristine lakes, and miles of hiking trails to explore.

• Springtime brings warmer weather and melting snow, making it the perfect time to go hiking and camping.
• In the summer, you can go hiking, camping, fishing, and canoeing.
• In Autumn, you can explore the many covered bridges in the area and drive New Hampshire’s scenic Kancamagus Highway to see the famous New England fall foliage.
• And in winter, the mountains of New Hampshire turn into a playground for cold-weather sports enthusiasts, with numerous ski resorts and cross-country skiing trails.

No matter what time of year you visit, there are plenty of things to do in the National Forest. Some of the most popular activities are hiking to the top of Mount Washington (the highest point in the Northeastern U.S.), driving the scenic Kancamagus Scenic Byway, and photographing the many covered bridges in the area.

ⓘ TIP: Download this self-guided Kancamagus Scenic Byway driving tour to ensure you don’t miss anything on the way. Directions, local tips, and fascinating behind-the-scenes stories play automatically, based on your location. The app runs offline using GPS; no cell service needed.

Where to spend the night in the White Mountains

North Conway is the perfect end to your day in New Hampshire, as it has a wide range of lodging options. You won’t have any problem finding a place to eat either, as it has many of New Hampshire’s best restaurants, shops, and attractions.

• Budget: Colonial Motel features an outdoor swimming pool and a picnic area. Some rooms feature a covered porch while others have a large spa bath.
• Mid-range: Cranmore Inn bed and breakfast is a short walk from the Conway Scenic Railroad and Mount Washington Observatory Weather Discovery Center. It features uniquely-decorated rooms with free Wi-Fi.
• Luxury: White Mountain Hotel and Resort Set within the natural beauty of Hale’s Location, this elegant North Conway resort features a year-round heated outdoor pool and hot tub overlooking the mountains. Rooms feature flat screen TV’s, work desk, USB Ports and Speakman showers. Daily full breakfast is included and high-speed internet access along with two dining options with Ledges Restaurant and Tullamore Tavern are also provided.

Day 4: Vermont’s Green Mountains

Today is all about Vermont, the Green Mountain State. The state gets its name from two French words, vert (green) and mont (mountain). When you see these mountains, you’ll understand why!

This morning begins with a two-hour drive to Stowe Vermont. Stowe is a popular ski resort town in Vermont, and it’s also home to some of the best maple syrup in the state. Be sure to visit one of the many sugarhouses in the area to see how this delicious treat is made!

You can also explore Stowe’s charming downtown, ski at Trapp Family Lodge, go for a hike in the Green Mountain National Forest, or take a scenic drive on the Mountain Road.

After lunch in Stowe, this afternoon’s road trip itinerary is all about the scenery as you drive down the Route 100 Scenic Byway. Vermont’s longest highway takes you through some of the most beautiful countryside in Vermont. You’ll see covered bridges, mountain vistas, and quaint towns all along the way.

Keep your camera handy; the covered bridges of Vermont are some of the most beautiful in New England. Visit Vermont has a page listing covered bridges along your drive.

Where to stay in Wilmington Vermont

Stop for the night in Wilmington, VT. Wilmington is a small town located in the southwest corner of the state, right on the border with Massachusetts.

This quaint town is home to several art galleries, antique shops, and a variety of restaurants. It’s also the perfect place to relax after a long day of driving.

• Budget: Viking Motel offers free WiFi access, cable TV, and air conditioning in all rooms.
• Mid-range: The Nutmeg provides accommodations with a garden and free WiFi throughout the property as well as free private parking for guests who drive. The inn features family rooms.
• Luxury: The Wilmington Inn provides accommodations with a bar, free private parking, a shared lounge and a garden. Featuring family rooms, this property also provides guests with a terrace. Free WiFi and a concierge service are provided. Vegetarian, vegan, and gluten-free options are available for breakfast.

Day 5: Litchfield and Mystic, Connecticut

Your first stop today is the small town of Litchfield, located in the western part of Connecticut. The prettiest drive is down US-7 S, and it travels through Litchfield Hills, one of the nicest parts of Connecticut. This route takes roughly the same amount of time as I-91 (about 2.5 hours). You decide!

Litchfield is a charming New England town with a rich history. The town was founded in 1719 and has been home to many notable residents over the years, including writer Harriet Beecher Stowe and abolitionist John Brown.

Today, Litchfield is a popular tourist destination for its many antique shops, art galleries, and historic homes. If you’re interested in learning more about the history of Litchfield, be sure to visit the Litchfield History Museum.

You can also take a self-guided walking tour of the town’s historic homes and buildings, such as the Oliver Wolcott House.

After lunch in Litchfield, your New England road trip continues east to Mystic, Connecticut. Mystic is a historic seaport located on the Mystic River in southeastern Connecticut.

Today, Mystic is a popular tourist destination, best known for its maritime history and as the setting of the 1988 film Mystic Pizza.

The top attraction is Mystic Seaport Museum, which is one of the largest maritime museums in the world. This fascinating museum features exhibits on the history of whaling, shipbuilding, and seafaring.

If you’re looking for other things to do in Mystic besides visiting the museum, one of the most popular family attractions is the Denison Homestead , a 300-year-old family farm that offers a glimpse into early colonial farm life. Mystic also has a nice aquarium, which is a popular attraction on rainy days.

Outdoor options include hiking in nearby Bluff Point State Park and kayaking or canoeing on the Mystic River. You can also take a boat ride or go for a walk along the pretty waterfront.

Where to stay in Mystic, CT

• Budget: Pet-friendly Days Inn Mystic is within walking distance to sights in downtown Mystic, and a short drive away from the Atlantic Ocean. Free breakfasts, Wi-Fi, and onsite parking is included.
• Mid-range: The Taber Inne is an 8-minute walk from the beach and 2,300 feet from Williams Beach Park. Guests staying at the hotel can enjoy the indoor heated pool and free WiFi throughout the property.
• Luxury: Harbor View Landing  accommodations include cottages, free WiFi throughout the property, and free private parking for guests who drive. Featuring water sports facilities and a tennis court, the hotel is close to several noted attractions and only 1.8 miles from Mystic Seaport. The property has river views and a terrace.

Day 6: Newport, Rhode Island

Rhode Island, the smallest state in the U.S., is home to many historic towns. One of the most notable is Newport, which was once a summer retreat for the wealthy.

The seaside town of Newport is best known for its gorgeous mansions, which were built by some of America’s wealthiest families during the Gilded Age.

Start your visit with a tour of The Breakers, the grandest of all the Newport mansions, located on the elaborate estate of Cornelius Vanderbilt. Then, explore the grounds of Marble House, another one of Newport’s famous Gilded Age mansions. Be sure to also stroll along Bellevue Avenue to see all of the other lavish mansions that line this famous street.

ⓘ BUDGET TIP: If you take the Newport Scenic Trolley tour , free admission to The Breakers mansion is included.

In the afternoon, visit the International Tennis Hall of Fame, explore Fort Adams State Park, or relax on one of Newport’s many beaches. If you’d prefer to explore Newport itself, cobblestone streets, art galleries, museums, antique shops, and local restaurants await.

If you’re a water lover, consider taking a boat ride to Block Island, taking a scenic boat ride around Newport Harbor, or going for a sail on Narragansett Bay.

End your day with dinner at one of Newport’s great restaurants, and don’t forget to enjoy a delicious cup of coffee from one of the local cafes while you’re there!

Where to stay in Newport Rhode Island

• Budget: Near Newport’s Memorial Park, Motel 6 Newport offers free basic WiFi and rooms that feature a seating area. The Newport Marina is 2 miles away.
• Mid-range: The Admiral Fitzroy Inn , a historic bed and breakfast, offers elegantly decorated guestrooms featuring antique sleigh beds and hand-painted walls. Guests staying at the inn can enjoy a free gourmet continental breakfast served in the sunny dining room overlooking Thames Street. The property also features a rooftop deck.
• Luxury: Hotel Viking opened in 1926. This historic Newport hotel is a 5-minute walk to Thames Street and less than 1 mile from the Cliff Walk to the city’s historic mansions. Guests staying at the Viking Hotel can enjoy an on-site spa, indoor pool, and fitness center. On-site dining at the One Bellevue restaurant is also available.

Day 7: Cape Cod

You’ll spend today on Cape Cod, a peninsula located in southeastern Massachusetts. With nearly 560 miles of pristine coastline, Cape Cod has long been a popular summer destination for the rich and famous, including the Kennedy family, who have a compound in nearby Hyannis Port.

But it’s a favorite East Coast vacation spot for families, couples, and singles as well, because of its many beaches and quaint small towns. New England beach vacations are extremely popular.

Depending on the weather and your energy level, you might want to begin with a Cape Cod self-guided driving tour. The audio app gives you a flexible and affordable way to see all of the scenic Cape Cod on your own terms.

Alternatively, start your morning at Cape Cod National Seashore. With 40 miles of coastline, the seashore features many pristine beaches, hiking and biking trails, and lighthouses to enjoy.

After a few hours at the seashore, drive to the charming town of Sandwich for lunch. This historic town is home to many beautiful old homes and buildings, including a glass museum and Hoxie House, the oldest home on Cape Cod. Heritage Museums and Gardens is also a wonderful destination.

In the afternoon, head to Provincetown, located at the very tip of Cape Cod. Provincetown is a popular summer destination for its nightlife and vibrant arts scene. It’s also a great place to enjoy some fresh seafood.

Or, you could take a boat ride to Martha’s Vineyard or Nantucket. These two islands are both accessible by ferry from Cape Cod and offer a different vibe than the mainland. If that’s more your speed, consider this Martha’s Vineyard tour by a local who has lived his whole life on the island.

Other popular Cape Cod attractions include the Cape Cod Museum of Natural History (Brewster, MA), the Whydah Pirate Museum (West Yarmouth), and the scenic Cape Cod Trail, a 22-mile paved pathway that winds through 6 towns on the Cape.

Where to stay in Cape Cod

You can either stay in Cape Cod for the night or return to the mainland in the evening and stay in Plymouth for two nights.

• Budget: Viking Shores Motor Lodge , located 2 mi from the beach, features an outdoor pool. It is also a part of the Cape Cod Rail Trail Bike Path.
• Mid-range: Sandbars Inn in North Truro has air-conditioned accommodations with views of the sea and free WiFi. Some of the units have cable TV, a fully equipped kitchen with a dishwasher, and a private bathroom with a shower and a hairdryer.
• Luxury: Wequassett Resort and Golf Club is a 2-minute walk from the beach. This West Harwich waterfront resort offers an 18-hole golf course, free Wi-Fi, and brightly colored rooms that offer a sitting area and plush bedding. Guests can enjoy waterfront dining, swim in the seasonal outdoor pool, or relax in the hot tub. A fitness center, children’s playground, and tennis court are also available.

Day 8: Plymouth, Massachusetts

The town of Plymouth, Massachusetts began as a Puritan colony in 1620. Today, it’s best known as the site of the first Thanksgiving and home to Plymouth Rock, the famous landmark that marks the spot where the Pilgrims first landed.

Start your visit at Plimoth Patuxet (formerly known as Plymouth Plantation). This living history museum complex is a must-visit for families and history buffs. It includes a replica of the Mayflower ship and several original 17th-century buildings that you can visit.

After lunch, stop at Plymouth Rock for a photo and continue to Pilgrim Hall Museum in Plymouth’s historic downtown-harbor area, where you can learn all about the Pilgrims who settled in Plymouth in 1620.

The town’s downtown-harbor area contains several historic buildings, including the Plymouth Courthouse (built in 1754), the Jenney Grist Mill (built in 1636), and the Mayflower Society House (built in 1824).

End your day with a walk along Plymouth’s historic waterfront. Don’t miss the Plymouth Cordage Company Historic District, a National Historic Landmark that includes several 19th-century rope-making factories.

End your day with dinner and a stroll along the Plymouth Waterfront to watch the sunset over Cape Cod Bay.

Where to stay in Plymouth:

• Budget: Best Western Plus Cold Spring  features an outdoor pool with panoramic views of Cape Cod and rooms with a 32-inch LCD TV. Historic Plymouth Rock is less than one mile from this hotel. Plymouth Waterfront and the Mayflower II are both within a 20-minute walk from this hotel. The Plimoth Plantation is just a 5-minute drive from the hotel.
• Mid-range: Hotel 1620 Plymouth Harbor  is located across the street from historic Plymouth Harbor. It features an indoor heated swimming pool.
• Luxury: Rooms at Harbourtown Suites on Plymouth Harbor include a seating area with a sofa bed, a kitchen with microwave and dishwasher, cable TV, free Wi-Fi, and free private parking.
• Resort: Mirbeau Inn & Spa has a spa and wellness center, a restaurant, and a fitness center with Peloton® bikes. The accommodation includes a fireplace and free Wi-Fi access. Other facilities offered at the property include an onsite shop and free parking.

Days 9-10: Boston, Massachusetts

There’s no better place to cap off your 10-day New England road trip itinerary than in Boston, the capital of Massachusetts. This historic city is full of colonial character and charm. Plus, there are plenty of things to see and do, from exploring the Freedom Trail to watching a baseball game at Fenway Park.

Return your rental car before you do anything else. You won’t need it in the city, as you can navigate better by using Boston’s public transportation system and on foot. Besides, parking and traffic in Boston can be a hassle.

You’ll find details on how to get into Boston from the airport at the end of this article.

ⓘ PRO TIP: If it’s too early to check into your room when you arrive, don’t worry. Most hotels will stash your bags in a secure location and then deliver them once your room is ready.

As one of America’s oldest cities, Boston Massachusetts is full of historic landmarks and sites. Start your Boston adventure by walking the Freedom Trail. Known as one of the top things to do in Boston, this 2.5-mile (4 km) trail passes 16 different sites that are all significant to American history. You can do it yourself or get the full experience with a guided walking tour.

If time permits this morning, take a leisurely stroll through Boston Common, the oldest public park in the country.

Head to the iconic Quincy Market shopping district for lunch, and don’t forget to try a famous Boston Cream Pie while you’re there!

In the afternoon, choose activities based on your interests:

• History lovers – visit some of Boston’s famous historical sites, such as the Boston Tea Party Ships, the USS Constitution Museum, and the Paul Revere House.
• Sports fans – Tour Fenway Park, home of the Boston Red Sox baseball team
• Art lovers – stroll through the Isabella Stewart Gardner Museum or the Museum of Fine Arts

In the evening, dine at one of Boston’s many great restaurants. For a truly unique experience, try a seafood dinner at one of the city’s many waterfront seafood shacks.

Be sure to end your day with a stroll along the waterfront to watch the sunset over Boston Harbor.

Where to stay in Boston:

• Budget: in the heart of Boston, HI Boston is 5 minutes away from Boston Common and public transport. All rooms include free Wi-Fi. Guests can relax with a pool table and TV in the game room. A shared kitchen, coffee bar, and vending machines offering snacks and drinks are on-site. Bike storage is available.
• Mid-range: The Oasis Guest House offers free WiFi, shared outdoor terraces, and concierge service. Northeastern University is an 8-minute walk. Some rooms include a private bathroom. All rooms are nonsmoking.
• Luxury: The Newbury Boston  features a restaurant, bar, shared lounge, and garden. This 5-star hotel has a 24-hour front desk, room service, and free WiFi. The hotel has family rooms, and breakfast includes vegetarian and gluten-free options.

Day 10 of your New England itinerary depends on when you plan to depart.

If you’re leaving in the afternoon or evening, you have time this morning for a little more sightseeing. You could spend a couple of hours cruising on Boston harbor or go wandering through one of Boston’s neighborhoods before heading to the airport.

If you have a second, full day in Boston—or better yet, 3 days in Boston, you might want to take part in an interactive museum tour and become a part of the Boston Tea Party , take an Italian food tour in Boston’s North End, or go whale watching off the coast of Boston in a catamaran. If you plan it right, you might even be able to catch a Red Sox game at Fenway Park!

No matter when your flight departs, be sure to allow plenty of time to get to Logan Airport. Traffic can be heavy, especially during rush hour.

How to get to downtown Boston from Logan International Airport

The cheapest and easiest way to get to downtown Boston from Logan International Airport is by taking the MBTA (Massachusetts Bay Transportation Authority) Silver Line bus. The SL1 and SL2 buses both go to South Station, which is located in the heart of downtown Boston. The ride takes about 30 minutes and costs $2.75 per person.

However, it’s not that easy because you’ll still need to get to your hotel. It’s best to take a cab or Uber from the station to avoid hassling with luggage on public transportation.

The most convenient option is to book a private shuttle from the airport to your hotel and let someone else handle the bags and traffic.

Final thoughts about this New England road trip itinerary

And that’s a wrap on your 10-day New England road trip itinerary! We hope you enjoyed this trip and that you’ll come back to explore more of this beautiful region in the future.

What are the best months for fall colors in New England?

The best time to visit for fall foliage in New England is typically September and October. However, the exact timing for peak color can vary from year to year depending on weather conditions.

Use this map to find up-to-date information on current New England fall foliage color.

5 tips for taking a road trip through New England

1. Get a map. You’ll be traveling through some remote areas with spotty or no cell signal. If you don’t want to risk taking a wrong turn, either buy a paper New England map or download the offline version of whatever New England road trip map application you use. And if you can, familiarize yourself with it before you depart.

2. Use apps to find cheap gas. Two popular ones are Gas Buddy and Waze . Fuel always ends up being one of the most surprising and costly expenses on a road trip.

3. Track the weather daily. New England weather can be finicky, and changing conditions can take you by surprise. Keep a raincoat and sweater handy.

4. Book a few experiences along the way. Walking tours, food tours, and boat tours are a lot of fun and create wonderful memories. There are tons of great tours on offer, allowing you to get the most of the vast history and beauty that New England has to offer.

5. Always carry loads of water and snacks in the car. It’s convenient to have what you need on hand. Plus, you won’t waste time and money buying stuff at a convenience store.

5 New England photography tips

1. Rural country roads offer a wealth of photo opportunities, from quaint farms to rolling hills. These areas are often more rural and less populated than urban areas, so you’ll have plenty of chances to snap some beautiful shots. And because rural country roads are usually less crowded than city streets, you won’t have to worry about getting in anyone’s way.

2. Look for elevated vantage points whenever possible. While you’re out exploring, keep your eyes peeled for elevated vantage points. hop on a rock or climb a tree to get a better view of your surroundings. You might just be surprised at what you find!

3. Remember to keep your camera charged. That way, you’ll never miss a moment. A fully charged hattery will let you capture all the special moments, so always keep it topped up.

4. Bring multiple spare batteries for your camera. Nothing is worse than seeing a great shot and discovering your camera is out of power. Extra batteries are the best backup plan.

5. Bring your drone, if you have one. You’ll be glad to know that aerial photography is permitted in many parts of New England.

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Written by Linda

Linda is multilingual and has been to over 50 countries. Her insatiable love of travel, cuisine, and foreign languages inspired her to create As We Saw It, where she documents her trips, shares practical itineraries, and offers insider tips. She’s passionate about helping fellow travelers save time, money, and hassle, and loves to discover new places to explore.

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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Save this Northeast Road Trip Itinerary for later! 

• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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10 day New England Road Trip Itinerary (Portland to Boston Drive)

Looking to spend some time on the east coast by taking a road trip through new england this road trip itinerary will take you through some of america’s oldest cities and towns..

Get ready to be blown away by idyllic small-town vibes, white steeples with brick-red facades, fresh lobster rolls, whale watching, and history upon history on this New England road trip!

This New England road trip will take you from Portland, Maine up to Acadia National Park, then back down through Portsmouth and into Boston, Massachusetts.

🚗 When booking your New England Road Trip car rental online, I recommend using Discover Cars . They provide the best deals for car rentals in New England!

Prepare for yourself for this New England road trip by making sure you have all the gear you need to make the best of your time in the car!

Let’s jump in!

Quick Overview of the New England Road Trip Itinerary

Boston to portland maine map.

A quick summary of stops on your 10 Day New England Road Trip Itinerary

• Days 1-3: Portland, Maine (3-hour drive time on day 3)
• Days 3-5: Acadia National Park, Bar Harbor (4-6 hour drive time on day 5)
• Days 5-10: Portsmouth, New Hampshire, and Boston, Massachusetts
• Airports: Portland International Jetport in Portland, Maine (PWM); Logan International in Boston, Massachusetts (BOS)
• Transit: Rent a car for pick up at PMW and drop off at BOS

New England Road Trip Itinerary

The new england road trip itinerary days 1-3: portland, maine.

• Land at Portland International Jetport early in the day if possible and pick up your rental car
• You’ll want to book your stay for 2 nights in Portland

Where to Stay in Portland, Maine

The best accommodation option would be to stay in or very close to Old Port. This is the historic downtown area of Portland with many cute boutiques for shopping and restaurants within walking distance.

If the prices in this area are out of your budget, I would recommend staying at an accommodation in either Portland’s East End or West End as they are both near the heart of Portland, Old Port.

• The Portland Harbor Hotel | cute boutique style
• The Press Hotel | sleek and upscale style
• The Courtyard by Marriott Downtown/Waterfront | cost-effective option near all the fun sites

Day 1: Landing in Portland, Head Light, and Old Port

• Today you’ll see some great highlights of Portland including the lighthouse and Old Port
• Portland city drive time: 15-30 minutes around town, including the airport to Old Port

Start your morning off with breakfast at Becky’s in the West End. The blueberry pancakes are DELISH, however, the omelets are also great for a high-protein meal.

• Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101

After breakfast, head over to Portland Head Light State Park for a short hike! This is one of the most popular sites in Maine and offers incredible views out over Casco Bay.

You can even do a lunch picnic here! Wear walking shoes (or sandals if you’d like to hike down to the water) and do some rock climbing to get some beautiful pictures of the Portland Headlight.

Spend as much time as you want here–it’s so beautiful! (We came here twice!)

Pro-tip: Tie up your hair and bring a jacket as it’s pretty breezy and a little chilly here!

• Portland Head Light State Park | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107

In the afternoon, take an hour-long tour of the Wadsworth-Longfellow House which was Maine’s first house museum that opened up to the public. Longfellow was a national literary man of his time and most furnishings in his house are original or belonged to his family.

• Wadsworth-Longfellow Museum | Address: 489 Congress St, Portland, ME 04101

After getting your history fix, you can take a walk and explore Old Port. This area has many cute boutiques and fun restaurants to try out!

Stop by The Holy Donut for a delicious snack (even multiple times over a 2-day trip) with interesting flavors such as the Maine blueberry cake donuts or chocolate sea salt flavor.

• The Holy Donut | Address: 177 Commercial St, Portland, ME 04101

There are also so many restaurants lined up here that you can grab a quick lunch before doing all your shopping. Some recommendations include Duckfat (amazing Belgian-style fries with sauces) and The Honey Paw (ramen noodles and Asian infusion).

Or head over to the Maine Lobster Shack for a delicious lobster roll–nothing is better than this fresh-caught lobster. You can’t go wrong with the Maine Lobster Roll or the Brown Butter Lobster Roll, and try the Maine Root Soda while you’re here.

• Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101

Day 2: More of Historical Portland and Peak’s Island

• Today you’ll get some more historical experiences of Portland and explore Peak’s Island by ferry
• Portland city drive time: 10-15 minutes around town

The next morning, grab some breakfast at the Bayside American Cafe. With their delicious menu, you can’t go wrong – everything from Maine blueberry pancakes to Bayside eggs benedict!

• Bayside American Cafe | Address: 98 Portland St Portland ME 04101

After breakfast, check out another museum for the history buff: reserve a ticket to spend about an hour touring Victoria Mansion, a historical landmark that is one of the oldest in the country and known for its architecture and original interior design.

• Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101

After touring the mansion, grab lunch at Hot Suppa! This Southern diner (and what I would consider hipster) has delicious offerings such as the Mother Clucker.

• Hot Suppa | Address: 703 Congress St, Portland, ME 04012

After getting a good bite in, take a 17-minute ferry to Peaks Island for some more exploring; we spent half a day here and had so much fun!

As you get off the ferry, rent a little golf cart From Mike’s Carts to get around the area. You can grab Lisa’s famous cinnamon bun at Peak’s Café as you start your cart tour.

Use this map to help you navigate your way around Peak’s Island. Head north first so that you can end your drive on Seashore Avenue, which provides endless views of the ocean.

Partway through your drive on Seashore Avenue, you can park your cart along the road and take a short hike to Battery Steele, which used to be a military fortification now graffiti-covered.

If you have time, you can also drive around the neighborhood and check out some of the cutest coastal homes–make it a game to find the best-named house!

You can also check out the Fifth Main Museum on the island as well to learn more about the history of the Civil war and other exhibits.

Keep track of the ferry schedule so you don’t miss the last one! Before you go, grab an ice cream cone from Down Front, a small convenience store.

• Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101

Day 3: Close Out Your Portland Itinerary and Drive 3 Hours Toward Acadia

• Today you can choose your morning experience and then prepare for your drive to Bar Harbor
• Portland to Bar Harbor drive time: 3 hours

You can pack everything the night before and check out as you leave in the morning. Start off the day by heading back to Old Port to grab some snacks and breakfast in preparation to drive out.

Since you’ll be savoring your last moments in Portland, Maine, you can choose what you’d like to do:

• last-minute souvenir shopping in Old Port
• taking some last looks at Portland Headlight
• check out the Portland Museum of Art

You will want to leave Portland by 1 PM.

• Portland Museum of Art | Address: 7 Congress Sq, Portland, ME 04101

That’s everything for your 3 day Portland itinerary ! It’s about a 3-hour drive west to your next stop so you’ll want to have all your favorites (snacks, music, and conversation topics) ready to go!

The New England Road Trip Itinerary Days 3-4: Acadia National Park and Bar Harbor

• When you arrive in Bar Harbor, check into your hotel and get some dinner in town
• You’ll want to book a 2-night stay in Bar Harbor

Where to Stay in Bar Harbor

For accommodations, stay directly in Bar Harbor at a cute inn to get the best of your time. Keep in mind that cell service around these parts is spotty at best, so don’t be afraid to stop and ask for directions!

• The Inn on Mount Desert | affordable stay in Bar Harbor
• The Elmhurst Inn | old-fashion boutique style in Bar Harbor
• Acadia Hotel – Downtown | upscale stay in Bar Harbor

Day 3 Continued: Getting to Bar Harbor and Settling In

• Spend your time strolling through this charming small town
• Portland to Bar Harbor drive time: 3 – 3.5 hours

Continue your New England road trip itinerary and head west towards Bar Harbor, where Acadia National Park Pond is located. You should arrive in the afternoon and get lots of views of lakes and beautiful nature scenes.

Since you’ll be here later in the afternoon, head into Bar Harbor which offers a small-town feel and is a fantastic place to enjoy some delicious food.

We got ice cream cones every time we went (which was only twice!). While you’re at it, make sure to buy some snacks, maybe even a sandwich lunch to enjoy while in Acadia National Park Pond the next day.

This would be the time to grab souvenirs or do some window shopping in Bar Harbor. There are so many cute boutique shops to just browse through!

For lunner (lunch + dinner), Galyn’s is a cozy little seafood restaurant in a Victorian-era house that has options for outdoor seating.

Opt to sit out on the patio and enjoy the fresh air and views while you eat your clam chowder soup. If that’s not for you, they also have small plates, fettuccine, sandwiches, and many more options to choose from. It was wonderful!

• Galyn’s | Address : 17 Main St, Bar Harbor, ME

Day 4: Explore Acadia National Park Pond

• Get an early start at Acadia National Park and do all the exploring on the hiking trails and beaches
• Bar Harbor to Acadia drive time: 15 – 30 minutes going through the park

Continue your New England road trip and get an early start to Acadia National Park Pond, which is known as the “Crown Jewel of the Atlantic Seaboard” and it’s easy to see why.

Take your time in Acadia and explore all that it has to offer, you won’t be disappointed! The mountain views are incredible, the road is scenic and well-maintained.

The weather in Acadia is usually pretty nice, but it can get chilly in the evenings. Make sure to pack layers so you’re prepared for everything! I had a light jacket with me, but by midday, I was getting pretty warm from the sunshine and hiking.

One of my favorite hikes here is the Beehive Loop , which is a great way to get acquainted with the difficult trails.

If you are looking for an adventurous hike, this 450-foot cliff trail will get your heart pumping! As one of Acadia’s most popular hikes, expect steep granite staircases that challenge even experienced backpackers (think ladders and iron rungs), as well as exposed cliffs. The trail is about 1.4 miles roundtrip and can take anywhere from 1-3 hours.

Another more moderate hike is the Bubble Trail which branches into North and South.

Both trails are reasonable, but if you’re looking for a shorter trail, take the Bubble Rock trail to see “the bubble,” which is a huge rock shaped like a bubble sitting precariously on the cliff of the mountains.

If mountains aren’t your thing and you’re more of a beach lover, Sand Beach and Echo Lake Beach are great for swimming and hanging out. You’ll most likely come across Sand Beach first if you’re coming from the entrance at Bar Harbor, which will also bring you to the trailhead of the Beehive Loop.

At the beach, you can unpack your lunch and enjoy a nice view out into the ocean with the sun keeping you warm.

However, if you are hungry after your hiking expedition, enjoy lunch at Jordan Pond House where you can dine on traditional meals of New England that include lobster rolls, chowder, and more.

A popular fare here is popovers and tea and if you are like me who had no idea what a popover is… it’s a light roll made of egg batter and can be eaten with whipped cream or jam and tea. Delish!

• Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675

For more adventuring in Acadia, make the drive to Cadillac Mountain or Thunder Hole. Cadillac Mountain is the tallest mountain on the East Coast at just over 1,500 feet with unparalleled views over Frenchman Bay and beyond.

Finally, no road trip to Acadia National Park is complete without a stop at the famous Thunder Hole! Don’t forget your raincoat because it looks like thunder when waves crash into rocks down below, causing an amazing sound experience for visitors nearby.

After a long day exploring Acadia National Park head back towards Bar Harbor at night to enjoy dinner in town. Grab a seat at one of my favorite restaurants, the family-owned Side Street Cafe.

The staff is so welcoming and the restaurant really fosters an atmosphere of community. Everything here is amazing–from appetizers to sandwiches and burgers.

• Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

After all the energy spent at Acadia, get some much-needed rest before the long 5.5-hour drive to Boston!

The New England Road Trip Itinerary Days 5-10: Boston, Massachusetts (with a stop in Portsmouth)

Where to stay in boston.

Driving around Boston can get congested during peak traffic hours, which will make your trip take longer than expected if you don’t plan accordingly.

Because of that, we decided to stay outside of Boston proper. Our Airbnb was about a 30-minute drive to Boston, which was actually more cost-effective for us since we weren’t always going to be in Boston proper.

If you would prefer to stay in Boston, you may be able to save on driving time on congested roads.

• Hampton Inn Boston Logan Airport | 16-minute drive to Boston, typical hotel stay
• The Newbury Boston | 3-minute walk to Boston proper, upscale stay

Day 5: Make the 5.5-hour drive South to Boston, with a short stop in Portsmouth, NH

• Check out of your rooms and prepare for a long drive south to Boston
• You’ll want to book your rooms in Boston for 5 nights
• Bar Harbor to Bass Harbor Light Station Drive time: 30 minutes
• Bar Harbor to Portsmouth Drive time: 3 hours, 55 minutes
• You’ll make a lunch stop in Portsmouth and get the chance to explore for a short while
• Portsmouth to Boston drive time: 1 hour

As you continue your New England road trip itinerary and start your drive down to Boston, you can make a stop at Bass Harbor Light Station. This historic lighthouse is off the beaten path but definitely worth checking out if you would like to add another lighthouse to your list!

After taking some pictures of the lighthouse, continue on your New England road trip and make a stop in Portsmouth, New Hampshire.

With a population of approximately 21,000 people, Portsmouth is the 13th largest city in all of New England! It’s also home to the Strawberry Banke Museum which consists of 11 historic homes and buildings dating back as early as 1695.

You can grab lunch in Portsmouth from places like the Clipper Tavern, The Wilder, or The Franklin.

If you’re game for ice cream (which is always on my list), check out Annabelle’s Natural Ice Cream, made with only the best ingredients! Then take a walk down the main street and explore the town on foot.

• Annabelle’s Natural Ice Cream | Address: 49 Ceres Street, Portsmouth

You’ll see an iconic New England church and steeple right in the town center. Right along this street are some cool shops like the River Run Bookstore, a fun game store called Diversions and Games, and a cute international boutique shop, Ten Thousand Villages.

After walking through some shops and exploring a little in Portsmouth, hop back in the car and finish out your New England road trip in Boston!

Next up on your New England road trip: Boston!

Day 6: Walk the Freedom Trail

• You’ll explore the freedom trail on foot and really get to see all the history in Boston proper – prepare yourself, it’s a long day of walking!
• Boston city drive time: 15-30 minutes depending on your stay

Take the rest of the days and go at your own pace. In this section of the New England road trip, you will not be driving across state lines or going long distances anymore.

There is SO much to see that you’ll need to make your itinerary work for you! Consider your top historic sites and your level of energy for all the walking you might do in the city. With that said, let’s jump into exploring Boston!

Boston is home to so much history! On the top of your list to do in Boston, the Freedom Trail .

This trail is a must-see for anyone who visits the city! The Freedom Trail is a self-guided historic walking trail that leads you to 16 of Boston’s most iconic landmarks. It is 3 miles long and will take you a whole day to complete as you make stops along the way.

You’ll want to get started on the Freedom Trail in the Boston Commons (1) . From here, you can visit the information center to get yourself a map and ask any questions. You’ll know you’re on the trail by following the marked trail embedded in the sidewalk.

As you get started, you’ll see the Massachusetts State House (2) located on a hill, and following that will be Park Street Church (3) , which was one of the first landmarks travelers would see coming into Boston.

Next, you’ll come upon the Granary Burial Ground (4) , which has some of the most influential historic persons like Benjamin Franklin’s parents, Paul Revere, and John Hancock. After this you’ll come upon a small square where you can visit King’s Chapel & King’s Chapel Burying Ground (5) , which is America’s oldest running pulpit – the bell still rings to call worshippers into the church.

You’ll also see Benjamin Franklin’s statue (6), the Old Corner Bookstore (7), and the Old South Meeting House (8) where the Boston Tea Party began!

At this point, you are right in the middle of a commercial hub to grab lunch – we got the familiar and ordered a burrito at Chipotle. However, there are so many restaurants to choose from.

Continue your trek on the Freedom Trail after lunch to the Old State House (9) , which is Boston’s oldest standing public building.

The trail will then take you to the site of the Boston Massacre (10) of 1770 where the Redcoats and Boston civilians broke out in gunfire. You’ll see the site marked with a marker.

Next up is Faneuil Hall (11), the “home of free speech” and “cradle of liberty,” you’ll see the popular golden cricket weather vane. It is now a cool marketplace and is one of Boston’s most popular attractions!

There is something for everyone with its many shops, restaurants, and music venues all in an old-fashioned market atmosphere. Right outside the marketplace, you might spot jugglers and dancers giving a great show!

After a little shopping, you’ll continue walking towards Paul Revere’s home (12) where you can take a tour inside. Continue your trek on the Freedom Trail to the Old North Church (13) , where you’ll see a statue of Paul Revere – this was the site of his midnight run.

You can also grab a snack in this area at Mike’s Pastries as he has some of the most delicious cannolis (address mentioned below)!

After the Old North Church, you’ll come to Copp’s Hill Burying Ground (14) , which is the final resting place for many artisans and craftsmen in the North End of Boston.

You’ll then take a 20-minute walk towards the USS Constitution (15) , which is the oldest commissioned warship afloat that fought during the war of 1812. Today, it is managed by the US Navy. You can purchase tickets and actually walk on the ship and even go underdeck to see the cannons and rooms.

Finally, head towards the last site of the Freedom Trail, Bunker Hill Monument (16) , which is a 221-foot granite obelisk.

At this point, it is likely that you’re well into the afternoon so I would recommend booking an Uber to drive you back to the Boston Commons, which is most likely where your car is parked.

If you would rather continue walking, you could walk the 3 miles back toward the commons.

From here, you can choose a place to grab dinner and call it a night! You’ll be exhausted from all the walking and sightseeing you’ve just completed.

Day 7: Whale watching, Boston Harbor, and the North End

• After all the walking yesterday, take it easy and go whale watching
• Explore the Italian district of the North End

Boston is the perfect place for whale watching ! There are several tour companies along the water where you can book a trip to see the whales.

The best time to see the whales in Boston is during the months of May – October when the whales migrate during the warmer temperatures.

Book your Boston whale-watching tour!

Boston Harbor Cruises has experienced marine biologists and tour guides to give you information while you are on the cruise. They are also experts in knowing the best spots where whales like to hang out.

You’ll head to Long Wharf, which is near the New England Aquarium to get in line for the tour. On our whale-watching expedition, we went to Stellwagen Bank National Marine Sanctuary.

It took a few minutes of watching, but we did spot some whales!

A whale-watching tour can take anywhere from 3-4 hours. Wear a jacket as it will get cold when you’re in the middle of the ocean.

• New England Aquarium | Address: 1 Central Wharf, Boston, MA 02110

After your tour, you’ll be right in the Boston Harbor. From here, you can walk along the waterfront and explore some sites. You can relax at the Charles River Esplanade which is a walking path along the waterfront with plenty of benches.

If you would like some more Boston history, check out some of the museums such as the Museum of Science, the Boston’s Children Museum, or the Boston Tea Party Ships and Museum.

For dinner, head to the Italian quarter in the North End which is the oldest neighborhood in Boston and has some of the most delicious food.

If you’re not into Italian food then there is still plenty of great places to try out including sushi, burgers, or lobster rolls that are sure to please everyone in your road trip group!

For dessert, try out the cannolis at Mike’s Pastry as they have been making these delicious pastries since 1926. The lines can look intimidating as they go out the door, but it goes quickly and the staff is very aware of your status in line.

• Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8: Harvard University and Candle Pin Bowling

• Explore the college town of Harvard University
• Have fun candlepin bowling
• Boston to Cambridge drive time: 30 minutes – 1 hour depending on your stay

Boston is also home to many amazing colleges and universities. On this day of the New England road trip, we chose to take a visit to Harvard.

Start off by grabbing brunch at Le’s Vietnamese restaurant then check out the historic Harvard Bookstore.

After this, we wanted to take a walk around the Harvard Campus. Do note that visitors aren’t allowed within the buildings without a guest pass.

We just walked around the campus and noted the buildings as well as the plaques that were displayed. It was pretty cool to say that we went to Harvard!

If you’d like to experience Harvard University more deeply, you can book a 70-minute student-led tour to see everything the university has to offer. Either way, you’ll want to make sure that you don’t miss out on visiting Harvard Yard.

There are also three art museums and the Harvard Museum of Natural History to explore.

Book your Harvard Walking Tour

For a more relaxed New England activity, go candlepin bowling at Sacco’s bowling alley in Sommerville, which is about a 10-minute drive from Harvard University.

This type of bowling is a little different than what you might be used to. Candlepin bowling is played with smaller balls and the pins are thinner as well; it tends to result in more strikes which means more points!

Sacco’s does offer food for purchase so we ordered flatbreads off their menu for dinner.

• Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144

Day 9: Fenway Park, New England Holocaust Memorial, Boston Public Market, Cheers, and a Ghost Tour

• Revisit Boston proper: there is so much more to see that might have been missed on the Freedom Trail – take your last day to visit all those last sites
• Boston city drive time: 15-30 minutes depending on where you stay

I’m not much of a sports fan, but I really enjoyed a walk around Fenway Park where the Red Sox play.

It was built back in 1912 and has been around ever since, also displaying members of the team around the stadium. With a guided tour, you’ll be able to visit the stadium’s collections of photographs, artifacts, and more!

Boston also has a memorial for the persecuted Jews during the Nazi regime where you can visit the New England Holocaust Memorial.

After walking through the memorial, you’ll end up near the Boston Public Market, which is filled with produce and gourmet food. This is the perfect spot to grab lunch!

• New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Boston Public Market | Address: 100 Hanover St, Boston, MA 02108

If you’re a huge literary fan, you can visit the Edgar Allan Poe statue, which is so descriptive and very well-made. You can see one of his most notable works: The Tell-Tale Heart. The statue stands right across the street from the Boston Commons south of Boyleston Street.

Another iconic stop in Boston is to visit the Cheers restaurant filled with memorabilia from the show! It’s located on the other side of the Boston Commons where Edgar stands. You can grab dinner here and reminisce about the show.

• Cheers restaurant | Address: 84 Beacon St., Boston, MA 02108

For the brave, book a trolley ghost tour to hear bout Boston’s most haunted locations! The tour guides are historians, so you can be sure that the stories they tell will be accurate and interesting-we learned so much about the cemeteries and ghost sightings!

Fun fact: there’s a little girl who is regularly spotted right next to these gravestones!

Side Note: You can also spend one night in a historic hotel or B&B. Some of these places date back to the 1800s! Most hotels even offer their own ghost tours if you’re feeling brave enough to stay overnight at one of their historical spots.

As you hang out later in Boston, you can see the Massachusetts State House beautifully lit up in the night sky! You can grab dinner to go and have a picnic in the Boston Commons, which is a huge park area.

Day 10: Check out and return home

• Boston to Logan Airport drive time: 15-30 minutes depending on your stay

After exploring all you can in Boston, it’ll be time to head back home. Return your car to Logan International Airport and from there fly out to your home airport.

Summary of the 10 Day New England Road Trip Itinerary

• Breakfast at Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
• Explore Portland Headlight | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
• Get your history in at Wadsworth Longfellow’s place | Address: 489 Congress St, Portland, ME 04101
• Shop in Old Port and get a snack at the Holy Donut | Address: 177 Commercial St, Portland, ME 04101
• Grab food at the Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101
• Breakfast at Bayside American Cafe | Address: 98 Portland St Portland ME 04101
• Check out more history at the Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101
• Grab a Mother Clucker at Hot Suppa | Address: 703 Congress St, Portland, ME 04012
• Take the Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101
• Spend your morning experiencing the last of Portland: revisit Old Port, Portland Headlight, or explore the Portland Museum of Art
• Prepare snacks and drive 3 hours to Bar Harbor, where Acadia National Park is located
• Arrive and check into your accommodation in Bar Harbor
• Grab lunner at Galyn’s | Address : 17 Main St, Bar Harbor, ME
• Do some shopping and strolling in Bar Harbor – get some snacks for Acadia
• Get some rest!
• Start early – do a difficult hike on the Beehive Loop Trail or a moderate one on the Bubble Trail
• Eat snacks or your packed lunch at Sand Beach or Echo Beach
• Grab lunch or some popovers and tea at Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675
• Drive to Cadillac Mountain and enjoy the views and Thunder Hole to check out the cliffs
• Finish your day in Bar Harbor at the Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609
• Stop at the Bass Harbor lighthouse then make your 4-hour drive to Portsmouth, NH
• Grab lunch and ice cream – do some walking and shopping in Portsmouth
• Continue your New England road trip to Boston – check into your hotel
• Grab dinner – we got take-out pizza at a corner store and rested from our long drive
• Explore the Freedom Trail by walking to each site (3 miles long, but will take all day)
• Go whale watching at the Stellwagen Bank National Marine Sanctuary
• Explore the Boston Harbor: Charles River Esplanade, Museum of Science, Boston Children’s Museum, or Boston Tea Party Ships and Museum
• Check out the Italian Quarter in the North End
• Grab dessert at Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113
• Explore the college town of Harvard in Cambridge: Harvard Yard, Harvard Bookstore, Art Museums, Harvard Natural History Museum
• Experience New England candlepin bowling at Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144
• Check out the iconic Fenway Park where the Red Sox play
• Walkthrough the New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Grab lunch at the Boston Public Market | Address: 100 Hanover St, Boston, MA 02108
• Revisit Boston Proper – Edgar Allen Poe , and walking ghost tour , picnic in Boston Commons , do more shopping at Faneuil Hall Marketplace
• Grab dinner at the Cheers Restaurant | Address: 84 Beacon St., Boston, MA 02108
• Check out and return home

Map of the 10 Day New England Road Trip Itinerary

Options to Extend Your New England Road Trip Itinerary

If you have more time to spend on a New England road trip, here are a few other historic cities to stop: Concord, Massachusetts, New London, Connecticut, or Providence, Rhode Island.

• Concord, Massachusetts is also full of culture, museums, galleries, and shops. This was also the home to writers such as Emily Dickenson and Henry David Thoreau.
• Providence, Rhode Island is a small city with a lot of history and very friendly people. Be sure to check out the historic downtown area and the amazing restaurants.
• New London, Connecticut where you can visit the U.S Coast Guard Academy, Fort Trumbull State Park, and many more historical landmarks.

What to pack for your 10 Day New England Road Trip

Keep in mind that you’ll be in the car for a few hours, so also pack some comfortable clothes for a long New England road trip.

Boston can also be rainy, so you’ll want to make sure to have a rain jacket and/or water-resistant shoes for all the walking you’ll do.

Here is my recommended list:

• 4-5 tops or shirts
• 1 pair of leggings
• 1 pair of jeans
• 1 jacket (or rain jacket as it does get wet!)
• 1 pair of hiking boots or walking shoes
• 1 pair of sandals
• Sunscreen for Acadia

New England road trip itinerary

When is the best time to go on a 10 day new england road trip.

The best time for a road trip to New England is late spring through early fall. This region of the United States has a temperate climate with moderate temperatures, meaning you can usually avoid extreme heat or cold during these months.

In addition, this time of year offers more daylight hours and plenty of outdoor activities that are perfect for exploring!

You can also plan your road trip to New England during the autumn months, especially in late September to see the foliage change from green to beautiful oranges and reds. Take a drive through the White Mountains in New Hampshire for spectacular views of nature at its finest!

FAQs: 10 Day New England Road Trip Itinerary

Is boston worth visiting.

Absolutely! Boston is full of history and culture. From the Freedom Trail to Fenway Park, there are plenty of places to explore. The food in Boston is also fantastic with a variety of cuisines from Italian in the North End to seafood dishes on the waterfront.

How much money should I budget for a 10 day New England road trip?

It really depends on your budget and what activities you plan to do. For a mid-range budget, a good rule of thumb is to budget around $150-$200 USD per day for food and activities.

Accommodations tend to run between $100-$150 for stays that are close to the areas mentioned in this itinerary. Car rentals range between $80-$90 a day.

If you plan to travel with friends, you can save money by splitting the cost of the car rental and hotels. You can then set your own budget for food and fun activities.

Are there any special precautions I should take when driving in New England?

Yes, some roads can be narrow and winding so it’s important to be aware of the speed limit, road signs, and other drivers. It’s also a good idea to plan your route ahead of time so you know where you’re going.

You might find fog in the northern part of New England as well in the early morning. Be sure to know how to use your fog lights and take it slow.

When in Boston, be prepared for congested traffic, weird roundabouts, and confusing streets (from my own personal experience).

Final Thoughts: 10 Day New England Road Trip Itinerary

That’s a wrap on the ultimate 10 day New England road trip itinerary. New England is a beautiful destination with many historical landmarks, incredible coastal views, and delicious food!

Are you ready to explore New England? Check out these posts!

• 10 Day New England Road Trip (Portland to Boston)
• 3 Day Portland Itinerary
• Best Walking Tours in Portland
• One Day in Camden, Maine
• Boston to Wells Road Trip
• Day Trips from Boston by Train (MBTA Weekend Pass)

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My favorite travel tips + resources.

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page .

• Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare Skyscanner (for the lowest prices) before I book.
• For hotels, I go through Booking.com or book directly with Marriott (for points + rewards).
• When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays.
• For vacation rentals, use Vrbo or Marriott Homes & Villas .
• Expedia also has some great bundles for hotels, flights, and car rentals altogether.
• Car Rentals: I love renting cars through Discover Cars . They have been consistent and provide the best customer service.
• Trains in Asia: Trip.com has the best options!
• Trains in Europe: Trainline or Omio .
• Visa Application: For a hassle-free process, apply for your visa from iVisa .
• Travel Credit Card: I book all my travel (flights, hotels, car rentals) through Chase Sapphire .
• Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
• Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide .
• Entertainment: Looking for entertainment like sporting events, theater shows, or concerts? Book with Ticket Squeeze !
• Tech : Keep your internet browsing safe, secure, and fast with ExpressVPN
• Language Learning: The best place to learn a new language is through Babbel as you travel to countries you don’t know the language.
• What to Pack: I almost always travel by backpack . For products I like, check out my packing guide page for all the things I take with me on different trips.

Pafoua is the author and creator of Her Wanderful World. Pafoua writes from her numerous excursions about all things travel, from fun itineraries to creating memorable experiences on the road. When she’s not traveling, Pafoua loves a fun board game night with her friends or is snuggled up reading a good book. You can find her on Instagram @herwanderfulworld.

The Ultimate 5 Day New England Road Trip Itinerary

Hello, fellow road trippers! Are you ready to embark on a picturesque journey through New England? This 5-day New England road trip itinerary is designed to show you the best of this region’s charming towns, stunning landscapes, and rich history. As someone who loves hitting the road and has a soft spot for New England’s unique allure, I’m thrilled to share this journey with you.

Day 1: Boston, Massachusetts – The Historic Start

Starting Point – Boston : Begin your New England adventure in Boston, a city steeped in history and culture. Spend your morning walking the Freedom Trail , a 2.5-mile route that takes you to 16 historically significant sites. Don’t miss the Boston Common, the United States’ oldest public park.

Afternoon Exploration : In the afternoon, explore the cobblestone streets of Beacon Hill, known for its beautiful Federal-style rowhouses and quaint atmosphere. Enjoy a meal at one of the local eateries – Boston’s culinary scene is a delightful mix of traditional New England fare and modern cuisine.

Evening in Boston : As evening falls, head to the Boston Harbor or stroll along the Charles River Esplanade for stunning city views.

Day 2: Boston to Cape Cod, Massachusetts – Coastal Charm

Morning Drive to Cape Cod : On your second day, head to Cape Cod, a hook-shaped peninsula known for its quaint villages, seafood shacks, Martha’s vineyard and lighthouses. The drive from Boston to Cape Cod is about 1.5 hours, but take your time and enjoy the scenic journey.

Exploring Cape Cod : Once in Cape Cod, visit the Cape Cod National Seashore for its beautiful beaches and walking trails. Check out Provincetown for its art galleries and vibrant street life.

Overnight in Cape Cod : Spend the night in one of Cape Cod’s charming inns or bed and breakfasts, experiencing true New England hospitality.

Day 3: Cape Cod to Newport, Rhode Island – A Touch of Elegance

Journey to Newport : On day three, travel to Newport, Rhode Island, renowned for its stunning Gilded Age mansions and sailing culture. The drive takes about 1.5 hours, offering beautiful coastal views along the way.

Discovering Newport : In Newport, tour The Breakers, the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial preeminence in the Gilded Age. Stroll along the Cliff Walk, a 3.5-mile path that offers spectacular ocean views on one side and opulent mansions on the other.

Evening Leisure : Enjoy an evening in Newport’s historic downtown, dining by the waterfront and savoring fresh local seafood.

Day 4: Newport, Rhode Island to White Mountains, New Hampshire – Into the Wilderness

Morning in Newport : Start your fourth day with a leisurely morning in Newport. Perhaps take a sail around Narragansett Bay or explore more of the town’s historic streets and shops.

Drive to the White Mountains : Mid-morning, begin your journey north to the White Mountains in New Hampshire. This drive takes you into the heart of New England’s natural beauty. The journey is about 4 hours but feels shorter due to the stunning scenery along the way.

Exploring the White Mountains : Upon arrival, immerse yourself in the natural splendor of the White Mountains. Visit Franconia Notch State Park, where you can see the Flume Gorge, a natural granite gorge extending 800 feet at the base of Mount Liberty. The Cannon Mountain Aerial Tramway offers breathtaking panoramic views.

Overnight in the Mountains : Spend your night in a cozy mountain lodge or cabin. The White Mountains region offers various accommodations, from rustic to luxurious, allowing you to enjoy the serene mountain atmosphere.

Day 5: White Mountains to Portland, Maine – A Coastal Finale

Morning Hikes and Scenic Views : Wake up early to catch a sunrise in the mountains. If you’re up for it, enjoy a morning hike; there are trails for all skill levels, offering one last chance to soak in the natural beauty of New Hampshire.

Journey to Portland, Maine : After your morning in the mountains, set off for Portland, Maine, about a 2-hour drive. This charming coastal city is known for its vibrant arts scene, historic Old Port waterfront, and incredible seafood.

Discovering Portland : Spend your afternoon exploring Portland’s cobblestone streets, unique boutiques, and art galleries. The Portland Head Light, a historic lighthouse in nearby Cape Elizabeth, is worth a visit for its picturesque setting.

Evening in Portland : Conclude your New England road trip with a delightful dinner in Portland. The city’s culinary scene is a fusion of traditional New England flavors and innovative cuisine. Enjoy a meal at one of the waterfront restaurants, savoring the fresh catch of the day.

Reflecting on Your New England Road Trip

Your 5-day New England road trip itinerary has taken you on a journey through some of the most picturesque and culturally rich parts of the Northeast. From the historic streets of Boston to the coastal beauty of Cape Cod and Newport, the majestic White Mountains, and the charming city of Portland, you’ve experienced a tapestry of landscapes and lifestyles that make New England unique.

As you head home, you carry with you not just photos but memories of quaint towns, scenic drives, and the warm hospitality of the Northeast. This trip is more than just a journey through places; it’s an exploration of the heart and soul of New England.

I hope this itinerary inspires you to explore the diverse beauty of New England. Safe travels, and may your road trips be filled with discovery and joy. If you need any more tips or insights for traveling in New England or beyond, feel free to reach out. Happy travels!

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New England Wanderlust

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

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

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

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

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

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

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Tips For Planning A Trip To New England In The Fall

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Best Places To See On A New England Fall Road Trip

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

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

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

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

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

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

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

Some Things To Know About My Itineraries

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

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

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

10 Day New England Fall Road Trip Itinerary From Boston

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

10 Day Road Trip Overview

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

Breakdown Of The 10 Day Itinerary Option

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

Where To Stay In Boston:

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

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

Day 2: Explore Boston

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

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

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

Day 2: Optional Day Trip To Salem

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

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

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

Day 3: Drive To Bar Harbor & Acadia National Park

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

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

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

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

Where To Stay In Bar Harbor:

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

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

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

Day 4: Explore Acadia National Park

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

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

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

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

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

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

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

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

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

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

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

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

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

Where To Stay In Jackson:

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

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

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

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

Day 6 – Drive The Kancamagus Highway To Franconia, NH

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

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

Tips For Driving The Kanc:

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

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

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

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

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

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

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

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

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

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

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

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

Where To Stay Near Franconia:

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

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

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

Day 7 – Drive To Stowe Or Woodstock, VT

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

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

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

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

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

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

Where To Stay In Stowe :

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

Where To Stay In Woodstock :

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

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

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

Day 8 – Explore Stowe & Woodstock, VT

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

Best Things To Do In Stowe :

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

Best Things To Do In Woodstock:

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

Day 9 – Drive To The Berkshires Or Litchfield, CT

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

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

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

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

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

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

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

Where To Stay In The Berkshires:

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

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

How To Spend Your Time In Litchfield Hill, CT:

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

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

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

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

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

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

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

How to spend your time in Sturbridge, MA :

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

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

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

Optional Adjustments For The 10 Day Itinerary:

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

12 Day Road Trip Itinerary Option

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

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

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

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

Burlington & Shelburne, Vermont things to check out :

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

Vermont back roads driving itinerary near Stowe :

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

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

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

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

7 Day Road Trip Overview

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

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

5 Day New England Fall Road Trip Itinerary

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

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

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

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

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

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

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

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

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

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

3 Day New England Fall Road Trip Itinerary

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

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

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

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

Weekend New England Fall Road Trip Itinerary

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

Vermont Fall Road Trip Itinerary

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

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

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

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

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

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

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

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

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

New Hampshire Fall Road Trip Itinerary

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

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

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

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

Connecticut Fall Road Trip Itinerary Option

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

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

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

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

• New Milford
• Washington/Washington Depot

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

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

What To Pack For A New England Fall Road Trip

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

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

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

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

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

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

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

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

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

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

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

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

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

Does It Snow In New England In The Fall?

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

How Do To A New England Fall Trip On A Budget

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

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

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

Is Fall In New England Worth It?

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

More posts you may enjoy:

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

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

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

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Try This 7 Day New England Road Trip Itinerary

This New England road trip itinerary might just be perfect to help you knock off 3 states from your list in just one week.

Are you interested in traveling to New England but unsure of the best things to do in Connecticut or what to do in Rhode Island?  

Are you looking for Massachusetts vacation ideas that don’t involve the extremely pricey Boston accommodations?  

This itinerary is full of 7 days of activities including travel between cities.  

You may want to consider adding an extra day at the beginning or end of the trip if you live far away and have a significant travel time to get to New England.  

Days 1-2: Start Your New England Road Trip in Connecticut

This trip starts out in Connecticut.  

Specifically in the southeast corner of the state at the Foxwoods Resort and Casino.  

If you enjoy casino vacations then you will be more than happy to start your trip at the second largest casino in the US, which is actually made up of 6 separate casinos with over 22 types of table games, over 250 tables, and the only $1 blackjack tables in Connecticut.  

Foxwoods also has 4,800 slot machines, bingo games, and more.

However, you don’t have to be a gambler or even of legal gambling age to enjoy your stay at Foxwoods.  

Here are some of the other activities you could enjoy:

• Spas – Romantic Connecticut getaways wouldn’t be complete without one of the many Foxwoods spa packages.  Whether you just want to get your hair or nails done to start off your vacation or you are looking for complete pampering and a massage, you can purchase individual services or build a spa package that fits your individual needs at Foxwoods.
• Golf – Foxwoods offers golf packages for the award winning Lake of Isles course.  Some of these packages combine 18 holes of golfing with hotel accommodations, food & beverage vouchers, casino match play credits, and even spa credits.
• Bowling & Arcade – Whether you are bringing kids on your vacation or you are just young at heart you’ll enjoy the High Rollers Luxury Lanes (Bowling) and Tree House Arcade.
• Shopping – Not only does Foxwoods have high end boutiques, but now there is also an 80 store Tanger Outlet shopping center at Foxwoods all under one roof.
• Walking Trails and Museum – If you are looking for a break from the bright lights of the casino and want to get some fresh air, there are miles of walking trails along with the Mashantucket Pequot Museum that you can explore. It’s no East Coast National Park , but it’s just as gorgeous.
• Shows and Nightlife – Just as you would expect of a casino in Las Vegas, Foxwoods has plenty of shows and nightlife to entertain guests of all ages.

You could spend two full days at the Foxwoods Resort and Casino and still not get to everything on your list.  

However, if you are at all interested in the history of nuclear powered submarines, US Navy nuclear powered ships, or the history behind nuclear power, then you really should pull yourself away from the casino for a couple of hours to go explore the Submarine Force Museum in Groton, CT, home of the USS NAUTILUS.

The USS NAUTILUS is the world’s first nuclear propelled submarine and is docked next to the museum.  

There is an audio self guided tour so that you can explore this historic submarine for yourself.  

The museum is the only one of it’s kind owned by the US Navy, and has a large collection of artifacts, documents, and pictures on display.

Days 3-4: Continue Up the Coast to Massachusetts

On day 3 you’ll want to get an early start to make the 3 hour drive out to Provincetown Massachusetts, which is the furthest town at the tip of Cape Cod.  

I’ll start by adding a quick disclaimer that Provincetown (or P-Town as it is affectionately referred to) is known for being a vacation destination for the LGBTQ community.  So if you’re gonna hate, then go somewhere else, or better yet just stay at home.

If you reject the food, ignore the customs, fear the religion and avoid the people, you might better stay home. – James Michener

Now that we got that out of the way I’ll say that my husband and I absolutely loved Provincetown.  

There were rainbow flags flown outside pretty much every store, people were incredibly friendly, the town was very walkable, there were lots of great restaurants, bars, and small shops.  I don’t recall seeing a single chain restaurant.  We look forward to making the trip back out to Provincetown at some point in our future.

While in Provincetown there are plenty of activities to pack your day with.  

On your first day I’d suggest getting a lobster roll for lunch from a local restaurant on Commercial Street (the main shopping district through the town) then walking to the Pilgrim Monument and Provincetown Museum.  

Once inside, you can climb to the top of the monument where you can get some really spectacular views of Cape Cod, so don’t forget your camera!  

On the way back into town stop in an ice cream shop (there are plenty of them!) and enjoy a couple scoops while you finish walking around town and out onto the pier.

Whale Watching and Race Point Beach

On Day 4 you should rent bikes from a local shop down on Commercial Street and ride out on the well maintained bike paths to Race Point Beach .  

Sit out on the beach for a while and see if you can spot any seals swimming near the shore or whales out closer to the horizon.  

My husband and I were lucky enough to see both before turning back and riding our bikes back into town.

Once you return your bikes, head back over to the pier and go for an afternoon or evening whale watching tour with Dolphin Fleet of Provincetown.  

You definitely won’t be disappointed!

Here are two of our better pictures.  

The first one is of a humpback whale eating with his mouth wide open, and the second is of his tail sticking out of the water as he makes a deep dive back down under our boat.

Days 5-6: Back to Rhode Island

On Day 5 you’ll have about a 2.5 hour drive to get to Newport, RI, so you’ll have a little bit of time in the morning to get breakfast and maybe take one last stroll through P-Town before you hit the road.  

Aim to get to Newport at least by early afternoon.

Newport is the perfect type of town for staying at a local B&B.  

Staying at a B&B can give you the feeling of staying with a family friend and is a cozy place to call home for a couple of nights.  

You’ll also have more opportunity to talk with the owners and other vacationers for recommendations on local restaurants and activities to make sure you enjoy your stay.

Once you get checked in to your lodging accommodations it’s time to go out and explore!  

Historically, Newport was the vacation home to many wealthy New Yorkers so keep your eyes open and see how many beautiful mansions you can find.

I’d recommend that you start by driving down Bellevue Avenue (where a ton of these historic mansions are located) and then that you follow signs for the scenic ocean drive down Ocean Avenue.

If you are ready to get out of the car and stretch your legs, there is a 3.5 mile public walkway named the Cliff Walk which is a beautiful way to take in the views of both the coast and many of the ocean front mansions.

To finish off your day you could walk around the Thames Street shopping area and grab dinner and a bowl of fresh New England clam chowder at the historic Red Parrot restaurant.

Visit 5 Newport Mansions

Yesterday you had the chance to admire the historic Newport mansions from a distance, but today you’re going inside!  

The Preservation Society of Newport County now owns eleven mansions representing the Colonial, Victorian, and Gilded Age.  

Your best option for purchasing Newport mansions discount tickets is to buy the “Newport Mansions Experience” tour ticket.  This ticket allows access to up to 5 properties and is a significant discount from purchasing each ticket individually.  

You can purchase this ticket at the first mansion you stop at.

By far, the most famous of these, and a real “must see” is the Breakers Newport mansion, which was the summer home to the Vanderbilt family.  

If you are interested in seeing how these mansions were maintained between all of the cooking, cleaning, and grounds maintenance, then you should consider adding the “Servant Life Tour” at the Elms so that you can see “behind the scenes” to the places in the house that were intentionally kept out of view from family house guests.  

The Servant Life Tour includes a tour through the servant bedrooms, the kitchen, the laundry room, the coal cellar, and the boiler room.

Day 7: Never Fun to Say Goodbye

All good things must come to an end unfortunately.

Head out for one last stroll along Easton’s Beach and grab any souvenirs you may have forgotten to pick up along the way.

It’s time to head home.

How Was Your Trip?

I certainly hope you’ve enjoyed your 7-day vacation and all of these New England travel ideas.  

Do you have any suggestions for travelers booking a New England vacation?  

Did you get any great photos of whales on your Massachusetts whale watching tour?  

Which was your favorite of the Newport mansions?  

Let me know in the comments below!

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Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

5 Day New England Road Trip Itinerary

My friend Sheela was turning 50 and had only been to two New England states, Connecticut and Rhode Island. I planned a 5-Day New England Road Trip Itinerary to take her on starring a few of my favorite places in New England but staying southern enough to do in five days. We were given a zippy and fun bright red Mazda CX-50 to try, which added to the experience. I hope you can use our expertise to plan your next New England trip, maybe around a long weekend.

Because we are active women, we planned much of this trip around some of my favorite New England hikes . I also included the best of New England- the ocean, mountains, lighthouses, waterfalls, art, food, and covered bridges.

Table of Contents

Day 1 Ogunquit, Maine

We wanted to start with a chill day by the water, so I picked one of my favorite New England seaside towns, Ogunquit. If you have extra time, Kennebunkport is not far away. My favorite thing in Ogunquit is walking the coastal Marginal Way path to Perkin’s Cove for a seafood feast. Read more about what to do in Ogunquit .

We stayed at the Juniper Hill Inn.

Day 2 Portland and Peaks Island, Maine

The food scene in Portland is fabulous; there are lots of lighthouses to explore, and you can take a quick ferry to a New England island, Peaks Island , which is easily explorable by bike. Read about what to do in Portland, Maine .

We stayed at the Portland Regency Hotel.

Day 3 The Kancamagus Highway, New Hampshire

The Kancamagus Highway travels through New Hampshire’s White Mountains and the towns of North Conway and Lincoln. Along the route are waterfalls, scenic overlooks, and hiking trails. Here are a few of my favorite Kanc hikes. On our trip, we hiked the Lower Falls and to Sabbaday Falls. My favorite winter hike is in Lincoln Woods.

Although I love both towns, it makes the most sense to stay in Lincoln so you aren’t doubling back. Check out this property in Lincoln , but stop in North Conway for breakfast at Peaches.

Day 4 The Lakes Region, New Hampshire

The town of Meredith sits on the banks of Lake Winnipesaukee. It is one of my favorite spots in New Hampshire. And just a few miles away is one of my favorite mountain hikes in New England, Mount Major. The peak of the hike provides views of Mount Washington and the surrounding lakes.

I have always wanted to stay at Mill Fall at the Lake.

Day 5 Woodstock and Quechee, Vermont

On our last day, we visited one of the most “New England” of the New England towns, Woodstock. It has a perfectly quaint downtown with a town green, lots of artists, and covered bridges over mountain rivers. The Quechee Gorge is an easy but beautiful hike. Woodstock is nestled in Vermont’s Green Mountains. Read on for things to do in Woodstock .

For a splurge, check out the gorgeously elegant Woodstock Inn .

Here is a map so that you can see a basic outline of the trip.

The Mazda CX-50

This 5-seater SUV was a very fun way to explore New England. It is zippy and has every feature I wanted, including crash avoidance and blind-side indicators. I also appreciated the lower gas mileage than my current SUV. It handled beautifully around our mountain roads and gave me all the power I hoped for.

With this 5-Day New England Itinerary, you will definitely be moving quickly. If you have more time, you can easily spend two days at any of these stops. Are you planning a trip to New England soon?

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2 thoughts on “5 Day New England Road Trip Itinerary”

Looks like the perfect 5 day adventure!! Missed you at Sam’s OctoberFest!! Bob

I missed seeing you as well. I’m out in California for my best friend’s 50th.

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The Grand Tour of New England

15 days, 14 nights

If time allows and it is your first visit to New England, a self driving road trip tour covering all six New England states will allow you a true taste of the region and all of its beauty and diversity. After leaving Boston, you will find wide open spaces, a friendly and hospitable welcome, and wonderful accommodations. Your hosts and innkeepers will serve as local sightseeing guides pointing you toward those perfect places to enjoy the scenic beauty of New England.

                                                       Explore More Road Trips & Itineraries

Day 1 — Boston, Massachusetts

Most international visitors arrive in New England at Boston’s Logan Airport . Conveniently located just three miles from downtown, Logan’s international terminal allows for a speedy transfer through customs and immigration and into the city. There are a variety of ways to get into the center of Boston , including public bus, subway and taxi.

Remember not to rent a car until you are heading out of the city — you will not need a car in America's “Walking City” and parking fees downtown are particularly expensive. Most rental car companies will allow for downtown pick up or failing that, the short journey back to Logan Airport is worth it on your day of departure from the city. Boston is the capital of Massachusetts and the unofficial capital of New England. A sophisticated and charming city, it is relatively small and walking is the best way to get around. Many international visitors feel very comfortable in Boston as it is the most 'European' of all American cities, with distinct small neighborhoods such as the North End , filled with lively Italian restaurants and cafes; the Back Bay, where wonderful shopping streets are filled with every designer shop imaginable; and Beacon Hill, with its cobbled streets and brown brick townhouses. Spend at least two nights in Boston to get the best feel for the city.

Places to stay in Boston

Day 2 — Boston

Spend the day exploring Boston’s unique history and locale. Here are some ideas to get you started:

• Walk the Freedom Trail.  A great way to easily see a lot of the city, the Freedom Trail links 16 places of historic interest throughout the city. You can begin anywhere along the route, but it is easiest to begin at Boston Common where the Visitor Center is located.
• Take A Duck Tour. The "Ducks" are amphibious vehicles that are able to travel both in water and on land. Boston Duck Tours  offer a wonderful perspective of Boston and Cambridge: see the skyline from the Charles River and hear about the unique sights of the city from your Boston driver!
• Other great ways to see the city include Trolley Tours , which allow you to hop on and off the trolley, or a cruise on Boston's beautiful harbor .
• Tour Fenway Park. Fenway is America’s oldest baseball park, home of the iconic Green Monster. Tours of Fenway Park are offered year-round, and if you visit during baseball season (April to September), you can also catch a Red Sox game.
• Consider putting aside some time to visit some of Boston's rich cultural gems, such as the JFK Library , the impressive Museum of Fine Arts , and a favorite for kids, the New England Aquarium .

Day 3 — Boston to the Maine Coast

Leave Boston today to begin your road trip and head north up the coast and into Maine . Time allowing, you should stop and visit any one of the wonderful small towns on the coast . Salem, Mass. , is known for the infamous Salem Witch Trials and is home to the amazing Peabody Essex Museum , whose collections include art and cultural artifacts from all over the world. A little farther north is the pretty artist colony of Rockport. A helpful note: most highways in New England have speed limits of 55-65 miles per hour (90-105 km/h).

The rugged state of Maine is as big as all the other New England states put together; on this tour, you will explore a little of its spectacular coast. Picturesque fishing villages are nestled together along a dramatic coastline. Don't forget to sample some of Maine's fine culinary delights — lobsters and blueberries! You may prefer to stay in the southern coastal areas, in the beautiful coastal towns of York, Kennebunkport, and Ogunquit, or continue north to Portland, a lively port town with a rich historic and cultural heritage and a budding culinary scene.

Search for accommodations in: Portland, Maine • Ogunquit • York • Kennebunkport

Day 4 — The Maine Coast

Spend the day exploring the coast of Maine: a visit to Portland with its many small galleries, shops, restaurants and museums, is a treat for city-lovers. Maine’s smaller, coastal beach towns are especially popular for their family-friendly sandy beaches, fresh seafood and relaxed atmosphere. For a quintessential Maine experience, take a lobster boat ride from Perkins Cove in Ogunquit, or stop by one of the many lighthouses along the coast, such as the Nubble Light in York or the Portland Head Light . Many fine small museums that scatter the coast, like the Wells Auto Museum and the Ogunquit Museum of American Art . Freeport, Maine, is also a good day’s stop for outlet shopping in a beautiful New England village.

Day 5 — Maine to the White Mountains of New Hampshire

Today, drive west through Maine and into New Hampshire's White Mountains region .  The drive will be longer today as there are no major highways to take you east-west in this part of New England. In New Hampshire, beautiful shimmering lakes and high mountains dominate the landscape, as the road winds through pretty villages. A paradise for hikers in the summer and a playground for skiers in the winter , the scenic White Mountains provide the perfect backdrop for outdoor recreation or quieter relaxation. A day of traveling can end on a high note with a trip to the top of Mount Washington , the tallest mountain in New England (6,289 ft / 1,917 m). In the summer, you can get to the summit on foot, by car on the 8-mile toll roador via the Cog Railway on a steam train. In the winter, the auto road can still be traveled, but only on a snowcoach tour.

Day 6 — New Hampshire

Spend the day exploring northern New Hampshire . A wonderful tour for driving follows the Kancamagus Highway between Lincoln and Conway, one of the most scenic in the USA. It also offers a chance to visit the Flume , a natural granite gorge with wooden walkways and rushing waterfalls. If souvenir shopping is on your list, New Hampshire is also tax-free and North Conway is one of the premium outlet shopping areas in the region. You can also travel a little further south into the Lakes Region of New Hampshire . Lake Winnipesaukee, the largest lake, offers everything from great sailing and fishing to relaxing water cruises on paddleboats.

Find lodging in New Hampshire

Day 7 — into vermont's green mountains.

Continuing the tour westwards, Vermont is the next stop. The Green Mountain State is known for its pristine landscape, rolling hills and the romance of small communities where white church spires poke up between the mountains. There are many lovely places to stay in Vermont, and you can choose to stay in the northern , central or southern part of the state. You will have the opportunity to experience the twisting country roads, mountain views, small towns, art galleries, country stores, locally-grown food and working farms throughout the state. One suggested stop in Vermont is the the state capital city, Montpelier. It is the smallest state capital in the country with just 8,000 residents. The town looks like one you might have seen in the movies, and is dominated by the gold-leafed dome of the Vermont State House. Continue on to Waterbury and take a unique factory tour at the Ben & Jerry's Ice Cream Factory and then onto Stowe , a charming mountain resort town nestled at the foot of Mount Mansfield.

Day 8 — Vermont

On your first full day in Vermont, make time for a visit to Burlington , Vermont's largest city. Many points in town offer beautiful views of Lake Champlain and the Adirondack Mountains in New York. Burlington’s large student population gives it a great "buzz" — nightlife, restaurants and music halls are busy year-round. A pedestrian-only shopping street, Church Street , is the heart of the city with a mix of local and high-end boutiques, restaurants and bars. Burlington is also an ideal place to sample some of Vermont’s famous craft beer. Spend the night in Burlington, or get a head start on the next day’s travel by heading south. Route 100, the “Skier’s Highway,” winds down the spine of the Green Mountains, past ski resorts, lakes, and gorgeous views, with plenty of opportunity to stop for the night in quaint Vermont towns.

Find places to stay in Vermont

Day 9 — Vermont to The Berkshires, Massachusetts

From Vermont, head south and into the lovely Berkshire Mountains of western Massachusetts . Charming Stockbridge is the heart of a region packed with culture and charm. In summer, the hills are a hot spot for musical talent, as the Tanglewood Music Center becomes home to the Boston Symphony Orchestra. Summer theater and dance performances are abundant, as is cutting-edge modern art at Mass MoCA and fine art at the world-class Clark Institute in the lovely college town of Williamstown.

Search for lodging in the Berkshires

Day 10 — to connecticut.

Continue your journey southwards and into Connecticut . Stretching east from New York City, Connecticut’s varied landscape includes wooded hills, rural farmland, rocky shores, and wide beaches. Many areas have beautifully preserved clapboard homes set amidst well maintained villages like Essex and Chester .

Travel south until you hit the coast of Connecticut, where there are many small towns that are worth exploring. Mystic is a good choice for a stop. Visit the Mystic Seaport , a living history village with working craftsmen, the world-class Mystic Aquarium or the Mashantucket Pequot Museum , which depicts Native American life in southern New England.

Search lodging in Connecticut

Day 11 — newport, rhode island.

A must on any visit to New England, Newport is as famous for its seaport history and Gilded Age mansions as its superb summer festivals. The cliff top mansions are truly magnificent homes, many built by the wealthy industrialists of the nineteenth century as a place to escape the summer heat of New York City. Beautifully preserved, you can tour 11 of these historic homes from different periods in American history. Save time to stroll along the Cliff Walk , with great views of the ocean, or to enjoy the downtown fun of Newport.

Places to stay in Newport, Rhode Island

Days 12-14 — cape cod, massachusetts.

A perfect way to end your visit to New England is to stay for a few days on beautiful Cape Cod . Base yourself in any one of the charming small towns and villages along the Cape and enjoy spectacular beaches, museums, music festivals, antique stores, sailing, great golf courses, and whale watching. Spend a couple of days in Cape Cod, enjoying the beaches, sun and sand on the high dunes and long beaches of the National Seashore . You can also explore the small towns and villages of Cape Cod, characterized by beautiful clapboard architecture, faded to a dusky grey from salty air. From spring until autumn, you can take a whale watching boat tour from many parts of New England — the feeding grounds for the humpback and finback whales are found just 30 miles (50 km) off the Massachusetts and New Hampshire coasts. These magnificent creatures played a huge role in New England's history: the whaling industry flourished here. Today, whales are protected but the history of whaling in New England can be seen at several area museums. A day trip to Martha's Vineyard or Nantucket is an option as well — ferries to the islands run year-round, though passages are more frequent in the summer months. The best way to explore the beautiful island landscapes is on a bike. Nantucket Town is a sight to see, thanks to its Georgian houses, old-fashioned street lights and brick pavements. Martha's Vineyard is closer to mainland Cape Cod, and a little larger, with several distinct and interesting towns. Both islands have great shopping, lovely sights, and the freshest seafood you can get.

Find lodging in Cape Cod, Martha's Vineyard and Nantucket

Day 14 — Cape Cod & Plymouth

History enthusiasts, don't leave New England without a trip to Plymouth, Massachusetts, and the Plimoth Patuxet (formerly the Plimoth Plantation). Plymouth is where the first Pilgrims settled back in 1620 after first landing in Provincetown. Plimoth Patuxet is a recreated Pilgrim settlement, where costumed interpreters work, eat and speak as the 17th-century colonists did while Native Americans demonstrate traditional methods of building homes and canoes.

Day 15 — Boston for Departure

Cape Cod is approximately a two hour's drive from Boston (depending on your exact location on the Cape), so depending on your flights, you may want to relax on the beaches of the Cape this morning or start the day in Boston. After a grand tour of this size, a leisurely morning is just the ticket.

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