The Ultimate New England Road Trip Itinerary (Updated 2024)

by Global Viewpoint
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Looking for the ultimate New England road trip itinerary to help you discover the best spots in all 6 states? This New England driving tour has got you covered!

From coastal cities and towns to mountain resorts, New England is the perfect place for road trips. Once the cold weather is behind us, Bostonians like myself set out for day trips, weekend getaways, and even multi-week road trips to see all this region has to offer. 

That’s why I’ve created this ultimate road trip itinerary for New England, which covers all six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

The ultimate New England road trip itinerary Pinterest image
New England tours to consider in 2024

Making the Most Incredible New England Road Trip

Though you’ll need at least 3-4 weeks to see it all, you can cover many of these New England trips in just a few days. Most people don’t have time to finish it all in one go, so consider breaking it up into a few separate trips this summer and fall.

Below is everything you’ll need to know for a New England road trip in 2024. This includes a road trip map, 30-day itinerary, top destinations (winter, summer, and fall), and other trip-planning tips.

Road Trip Itinerary Map for New England

This map shows all the main stops along this road trip itinerary for New England. I will cover these destinations in more detail below and explain how to make your itinerary as efficient and easy as possible.

Days 1-2: Boston, Massachusetts

Start your road trip in the beautiful city of Boston. It’s home to Logan International Airport and various rental car companies, so most visitors will inevitably begin their adventure here.

The Boston Public Garden is a must-see in the heart of Boston.
The Boston Public Garden is a must-see in the heart of Boston.

What to Look out for on a New England Tour Through Boston

As the largest city in New England, Boston is a hub of culture, history, architecture, and food. It’s a bustling, world-class city with a small-town feel to it. There are so many amazing restaurants and dessert venues in Boston; it can be a bit overwhelming! 

Here are my favorite spots in Boston that you should check out:

  • The Freedom Trail: 2.5-mile walking path around historic sites and museums. Be sure to eat at either Union Oyster House or Warren Tavern, which are among the coolest restaurants in Boston!
  • Beacon Hill: A historic neighborhood with iconic brick buildings. There are some amazing Airbnbs and VRBOs in this part of Boston MA!
  • Boston Common and Public Garden: Scenic public parks in the heart of Boston. In the winter, be sure to go ice skating on Frog Pond!
  • Faneuil Hall: A historic marketplace filled with restaurants and street food vendors.
  • Boston Harborwalk: A waterfront promenade with stunning views of the Boston skyline.

More Boston Sights You’ll Want to See

  • Charles River Esplanade: Another popular path for a stroll or bike ride. If you have time, head over to Cambridge which lies on the other side of the Charles River.
  • Newbury Street: An upscale shopping street lined with boutiques and restaurants.
  • Rose Kennedy Greenway: A public space lined with greenery, food trucks, and more.
  • The North End: Boston’s version of “Little Italy” with amazing Italian restaurants.

From its colonial heritage to its hip cultural scene, Boston has plenty of cool things to see and do that will keep you entertained for at least a couple of days. Then, you will be ready to explore more of New England.

Read next: 11 Unique Stays in Massachusetts

Acorn Street in Boston is one of the most photographed streets in the US.
Acorn Street in Boston is one of the most photographed streets in the US. Check out my Etsy shop for a high-resolution wall print or canvas:

Day 3: Salem, Rockport, and Gloucester, Massachusetts

Salem, Massachusetts

Home to the notorious Salem Witch Trials that occurred in the late 1600s, Salem is a must-see for history enthusiasts. This coastal city brims with historic landmarks, museums, shops, and restaurants that can be covered in a few hours. 

Here are some sights most visitors will not want to miss:

  • Salem Maritime National Historic Site: A cluster of 12 historic structures along the Salem Harbor waterfront.
  • Salem Witch Museum: A museum set inside a 17th-century home that covers the Salem Witch Trials.
  • The House of the Seven Gables: A colonial mansion built in 1668 made famous by Nathaniel Hawthorne’s novel, The House of the Seven Gables.
  • Peabody Essex Museum: One of New England’s largest museums, home to a vast collection of American and Asian art.

With all its witch-themed museums and shops, Salem has a bewitching feel (especially in October around Halloween). But even if witch paraphernalia isn’t your thing, you’ll still appreciate the authentic New England charm of one of America’s oldest fishing villages.

The House of the Seven Gables in Salem, Massachusetts
The House of the Seven Gables in Salem, Massachusetts.

Gloucester, Massachusetts

Just northeast of Salem is Gloucester, a popular beach destination amongst locals. Two noteworthy beaches to visit on a hot summer’s day are Good Harbor and Wingaersheek. Most beachgoers prefer Good Harbor, but Wingaersheek is preferable for families with small children because there’s very little of an undertow.

Apart from relaxing on the beach, the main things to do in Gloucester are eating seafood and checking out the iconic Fisherman’s Memorial Monument. Then, head next door to Rockport.

Gloucester Fisherman’s Memorial
The Gloucester Fisherman’s Memorial pays tribute to all the local fisherman who lost their lives at sea. Hundreds of names are inscribed around the memorial; it’s really moving and shocking to see.

Rockport, Massachusetts

Rockport is the quintessential New England town. It is set on the windswept Atlantic coastline and is chock-full of quaint shops, galleries, and restaurants. Drawing visitors with its seaside village vibe and lingering smell of fresh seafood, Rockport is one of my favorite day trips over the summer.

Here’s what you should check out in Rockport, Massachusetts:

  • Bearskin Neck: The main shopping street in Rockport is lined with shops and eateries.
  • Motif Number 1: An iconic red fishing shack that perfectly complements the surrounding landscape.
  • Halibut Point State Park: A conservation area with scenic walking trails.
  • Front Beach: A small beach within walking distance of Rockport’s downtown.
  • Long Beach: A longer beach (haha) that connects Rockport and Gloucester.

Rockport can get pretty crowded over the summer, so it pays to get there early when the shops open.

Listen to the waves and seagulls, eat a lobster roll, and soak in the charm of one of America’s finest fishing villages.

Bradley Wharf in Rockport
Motif Number 1 is nestled along Bradley Wharf in Rockport.

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Alternative Road Trip Idea in MA: Newburyport

If you have the time, consider stopping in Newburyport before heading north into NH and ME. This coastal town is just 35 miles north of Boston, but it feels world’s apart with its relaxed vibe and charming maritime heritage.

Plum Island near Newburyport
Plum Island is a beautiful nature area near Newburyport that everyone should visit on a New England road trip.

Go on a self-guided food tour around this seaside city. Hit one of the beaches, museums, and parks it offers. As a local, I must say – Newburyport has one of Massachusetts’s best restaurants and shopping scenes. It’s definitely a must-see on a trip to New England.

A vibrant turquoise 1955 Chevrolet Bel Air captured in a photograph
Touring New England? Don’t miss Newport’s quaint downtown.

Day 4: Coastal Byway, New Hampshire

Nestled between Maine and Massachusetts, New Hampshire’s Coastal Byway extends just 18.5 miles along the Atlantic shoreline. It passes several beaches, historic forts and mansions, and state parks.

These are some of the top things you should see along New Hampshire’s Coastal Byway:

  • Hampton Beach: A beach resort town with a bustling beach and boardwalk.
  • Odiorne Point State Park: A beautiful state park along New Hampshire’s rocky coast.
  • Strawbery Banke Museum: An open-air museum with over 37 buildings built between the 17th and 19th centuries.
  • Prescott Park: 10 acres of fields and gardens where summertime concerts are held.

The highlight of any road trip along the Coastal Byway is Portsmouth, a historic city with lots of New England charm. I recommend spending a few hours strolling its cute streets, dining at one of its restaurants, and sampling a local beer or two before continuing north to Maine. Be sure to take in the sights of the Maine coast.

Tugboats in Portsmouth, New Hampshire
Tugboats in Portsmouth, New Hampshire.

Day 5: York, Ogunquit, and Kennebunkport, Maine

This road trip wouldn’t be complete without visiting Maine. It’s nicknamed “the way life should be,” and you’ll quickly find out why as you venture up the striking Maine Coast.

Perkins Cove in Ogunquit, Maine
Perkins Cove in Ogunquit, Maine

Spend at least a day exploring Maine’s southern coast, stopping by seaside towns like York, Ogunquit, and Kennebunkport. These are some of my absolute favorite beach towns in ME. Here are some of the coolest spots in this region:

  • The Marginal Way: A scenic, coastal trail in Ogunquit. It’s a must-see place on a Maine road trip itinerary.
  • Perkins Cove: A tiny cove with fishing boats, classic boutiques, and restaurants that serve some of New England’s freshest seafood. Clam chowder and lobster, anyone?
  • Nubble Lighthouse: An iconic New England lighthouse in York, Maine.
  • Ogunquit Beach: A vast stretch of beach perfect for swimming (if you’re brave enough to dip in the freezing cold water).
The Marginal Way in Ogunquit, Maine
The Marginal Way in Ogunquit, Maine

These places can easily be covered as a day trip or weekend getaway from Boston. They are also convenient stops along the way to Portland and Bar Harbor, Maine, which lie ahead on this New England itinerary.

Day 6: Portland, Maine

Located 45 minutes north of Ogunquit and 2 hours from Boston, Portland is an awesome place to spend a day or weekend.

Boat docked at dock in front of row of houses in Portland, Maine
New England tours bring you to Portland

This seaport city is home to an eclectic mix of museums, art galleries, breweries, and restaurants. Portland is best known for its Old Port—the historic center of town— dotted with quaint cobblestone streets and brick buildings from a bygone era. Here, you’ll also find plenty of eateries serving traditional, Maine-style seafood. Yum!

If you’re into craft beer, you should also check out Portland’s brewery scene, which includes well-known brewing companies like Allagash, Bissel Brothers, and Shipyard.

Portland is also a great destination for sightseeing, where you can hop aboard a ferry to explore Casco Bay or even drive down the road to check out Portland Head Lighthouse.

From Portland, it’s just a 3-hour drive to Bar Harbor and Acadia National Park, which is the highlight of any New England road trip itinerary.

Tip: On the way up to Acadia from Portland, be sure to make a stop in Freeport, Maine. This town is home to the L.L. Bean Flagship Store and many other outlet stores.

Portland Head Lighthouse
Portland Head Lighthouse

Days 7-9: Bar Harbor & Acadia National Park, Maine

Acadia National Park is New England at its finest. This treasure in northeastern Maine is home to some of America’s most incredible biodiversity and landscapes. You should plan to spend at least 2-3 nights here to cover the main sights. However, if you want to take your time and see all that Acadia and Bar Harbor have to offer, I’d recommend spending up to a week here.

Jordan Pond in Acadia National Park.
Jordan Pond in Acadia National Park

Exploring Acadia on a Northeast Road Trip

On the same day, you can witness the power of the ocean as waves batter rugged cliffs and then venture inland to see your reflection in the park’s crystal-clear lakes and streams. Here are some must-see sights in the National Park:

  • Park Loop Road: The main scenic road that crisscrosses the park.
  • Cadillac Mountain: A mountain with sweeping views of the Atlantic shoreline. For part of the year, it’s the first place in the U.S. where you can see the sunrise. It’s an awesome place to catch the sunrise and sunset (though be warned: in the summer, the sun rises at 4:30 am).
A man sitting on a rock, gazing at a serene lake surrounded by nature's beauty in Cadillac Mountain
Cadillac Mountain is a must-see on a New England road trip itinerary
  • Jordan Pond: A pristine lake with crystal clear water and a backdrop of mountains in the background. On a clear day, the visibility underwater can be between 45-60 feet.
  • Thunder Hole: A rocky inlet that lets out a thunderous roar when waves crash against it. (Note: your best chance of hearing this “thunder” sound is about two hours before high tide).
  • Sand Beach: A small beach tucked between mountains and rocky shoreline.
  • Eagle Lake: A gorgeous lake along Acadia’s scenic Carriage Road.
Eagle Lake in Acadia National Park
Eagle Lake is one of my favorite spots in Acadia National Park

During your trip to Acadia, you will likely stay in Bar Harbor, a coastal town near the park entrance. Lined with cozy shops, restaurants, and B&Bs, Bar Harbor has a wonderful summertime ambiance.

On the way back to New Hampshire, consider stopping at Baxter State Park, which lies further inland. It’s home to Maine’s highest mountain, Mount Katahdin (5,267 feet – 1,605 m), and a variety of fun hikes. The next section outlines this destination further.

Alternative Road Trip Suggestion in Northern Maine: Baxter State Park

Looking to venture inland from the coastal highlights of ME? Add to your road trip through New England by stopping at Baxter State Park. This vast wilderness area is home to Maine’s tallest mountain, Mt. Katahdin, and other landscapes, including forests, lakes, ponds, rivers, and streams.

Beautiful waterfront views with Katahdin as a backdrop
Beautiful waterfront views with Katahdin as a backdrop

Baxter State Park is the northernmost point of the Appalachian Trail. It’s an awesome destination for hiking, camping, fishing, and more. Stay in a log cabin overlooking a glacial lake or a campsite with views of the crown jewel, Katahdin. Though this state park is often overlooked by the coastal cities, towns, and nature areas in ME, it shouldn’t be missed if you have the time!

With over 200,000 acres of pristine woodland, it’s easy to see why Baxter State Park deserves a mention among the best road trips through New England.

Scenic lake nestled among towering mountains and lush trees

Day 10: Rangeley Lakes Region, Maine

Nestled in the mountains of Western Maine, Rangeley is a popular stop en route to the White Mountains. This resort area is a great place to visit at any time of the year, providing plenty of opportunities for skiing in the winter, kayaking and hiking in the summer, and leaf peeping in the fall.

Photograph of autumn sunrise over the white mountains
A New England trip wouldn’t be complete without a visit to Rangeley

Rangeley is home to Saddleback Mountain, perfect for skiing, hiking, and camping. The region also has six major lakes that are among the most beautiful that you’ll find when road-tripping through New England. Here are some things you’ll want to check out during a visit to the western mountains of Maine:

  • Rangeley Lake State Park: Over 850 acres of pristine wilderness where you can view wildlife, go hiking, camping, and more.
  • Rangeley Lakes National Scenic Byway: This scenic New England driving tour is perfect for chasing fall colors and wild moose!
  • Saddleback Ski Mountain Maine: This unique lodge offers skiing in the winter. It’s said to have some of the best beginner terrain in the northeast.
  • Height of Land: A scenic overlook point on Route 17 that looks over the Rangeley Lakes region.
  • Bald Mountain: A prominent peak suitable for hikers of all levels with lake views.
  • Mooselookmeguntic Lake: One of the most beautiful lakes in Maine.
Aerial view of river winding through autumn forest, vibrant fall colors on trees, peaceful nature scene
It’s no wonder Rangeley Lakes is a top northeast road trip

Alternative Road Trip Suggestion: Moosehead Lake

If you have the time and want to see the second-largest lake in New England, visit Moosehead Lake. You won’t regret making this stop on a trip to New England!

Moosehead Lake is one of the best places in the country to spot a moose. The surrounding area, known as the Maine Highlands region, offers plenty to see and do for a few days. Explore idyllic rivers and lakes, go on an ATV adventure, and, of course, go skiing and bike riding. Traveling in New England is undoubtedly made better with a visit to Moosehead Lake!

Scenic aerial view of white mountains and lake in autumn
New England tour like no other

For a unique local experience on this New England trip, stay at a lake house. You won’t regret it!

An aerial view of a house nestled amidst vibrant fall foliage, showcasing the beauty of the season
Rangeley is home to gorgeous wilderness areas

Days 11-13: White Mountains, New Hampshire

The White Mountains region is a year-round destination on the east coast. It’s especially picturesque during the fall foliage season, but it’s also the perfect getaway in the summer for hiking and camping (and, of course, in the winter for skiing). Here are some unique places to explore:

  • Kancamagus Highway: Take a fall foliage tour on this 35-mile scenic route, where you’ll pass by beautiful forests, creeks, gorges, and waterfalls. It’s one of my favorite places to see the fall foliage in New England, when the fields and mountains are covered in red, orange, and yellow leaves.
  • Omni Mount Washington Resort: The Omni Mount Washington Resort is a historic and luxurious hotel considered one of New England’s most iconic buildings.
  • North Conway: A town hailed for its retail outlets and antique shops. Many amazing NH cabin rentals in this region will give you a proper taste of the White Mountains!
A scenic road surrounded by colorful autumn foliage and majestic mountains in the background
The White Mountains are a popular place for leaf peeping in the fall.

More New England Tour Ideas in the White Mountains

  • Clark’s Trading Post: A family-run trading post that’s basically a mini-theme park.
  • Franconia Notch State Park: A stunning park with miles of hiking, biking, and skiing trails. It’s a great stop during a fall road trip itinerary. This state park is home to Cannon Mountain, a 4,000 ft. (1,240 m) peak with a tramway that takes you to the top.

Another place worth noting is the Mount Washington Observatory, which lies on New Hampshire’s highest mountain, Mount Washington (6,288 feet – 1,916 m). It’s infamous for having the most extreme weather conditions on Earth. The highest wind gust ever recorded in the world (231 mph) occurred there in 1934.

There is so much to see in New Hampshire that you can easily spend a week or more doing a road trip around the whole state.

Mount Washington Resort in Bretton Woods, New Hampshire
Built in 1902, the Mount Washington Resort is a must-see in Bretton Woods, New Hampshire

Alternative Northeast Road Trip Suggestion in NH: The Lakes Region

Unlike the White Mountains, known for its adventure and dramatic mountain landscapes, the Lakes Region is a bit more subdued. Sure, you’ll find plenty of scenic mountains and outdoor activities, but the main draw is its lakes. If you’re looking to relax and unwind lakeside rather than pedal to the metal, this is the perfect place to visit.

Vacation rentals in Lake Winnipesaukee
Lake Winnipesaukee has some epic vacation rentals!

Lake Winnipesaukee Is a Must-See When Road-Tripping Through New England

Spend a weekend or longer at one of the 270 bodies of water scattered throughout the Lakes Region. The most famous is Lake Winnipesaukee, the largest lake in New Hampshire. Other popular lakes include Lake Sunapee, Ossipee Lake, Squam Lake, and Newfound Lake. Each of these lakes can be visited year-round with plenty of places to eat, shop, explore, and soak up the sun.

If you’re looking to go-go-go on this road trip through New England, perhaps choose the White Mountains instead this time around. This is one of those destinations where you’ll want to take your time at.

Take a step back to relax and savor the moment from an Airbnb or VRBO rental on Lake Winnipesaukee. It won’t be long until you see why this is one of the top places to visit on a New England tour!

A serene church by a lake, embraced by lush trees
The Lakes Region is a top New England road trip for those seeking a respite from busy modern life.

Day 14: Mad River Valley, Vermont

Located in the Green Mountains of Vermont, the Mad River Valley is a popular region when touring New England. It’s comprised of five resort towns: Duxbury, Fayston, Moretown, Waitsfield, and Warren, as well as two notable ski resorts, Mad River Glen and Sugarbush Resort.

The Mad River Valley on a Vermont New Hampshire Maine road
The Mad River Valley is a popular stop on a Vermont New Hampshire Maine road trip.

Some of the top things to do in the Mad River Valley include scenic drives, mountain biking, hiking, skiing, kayaking, and horseback riding. There are also farms in the area that serve some of the best cider donuts (and other seasonal specialties). Stay at a rustic log cabin in the mountains, or a charming B&B in town. It’s easy to see why visitors spend a night or more in the Mad River Valley during a northeast road trip.

Road along the Green Mountains in New England
Driving in New England is made better with a visit to the Green Mountains.

Days 15-17: Stowe and Burlington, Vermont

After exploring the White Mountains, head west to Vermont. You’ll be amazed by what you see!

Stowe, Vermont

Stowe is a year-round destination that makes you feel like you’re in Austria. It’s home to the Trapp Family Lodge, a mountain resort with amazing alpine views and Austrian-inspired food. Vermont is known for its farm-to-table dining; you’ll find some of the best of it here and in Burlington. 

Here’s what you should check out:

  • Mount Mansfield: The highest mountain in Vermont that offers hiking, zip lining, and mountain climbing. Be sure to take the Stowe Mountain Auto Toll Road up to the top.
  • Alchemist Brewery: A small, family-run brewery best known for its flagship double IPA, the Heady Topper. At 8% ABV, it certainly packs a punch, so make sure you have a designated driver!
  • Stowe Recreation Path: A lovely 5-mile path made for bike riding and hiking.
  • Smuggler’s Notch State Park: A popular sightseeing area in the mountains with verdant forests and raging waterfalls. When I was younger, I loved staying at the Smugglers’ Notch Resort.

After spending at least one night in Stowe, head west to Burlington. Admire the gently rolling hills and mountains, and don’t forget to stop by the Ben and Jerry’s Factory in Waterbury!

The Innsbruck Inn in Austria
The Innsbruck Inn definitely makes you feel like you’re in Austria.

Burlington, Vermont

Located on the shores of Lake Champlain, Burlington is an earthy-crunchy city with lots to offer on a New England and Vermont road trip. Burlington is very forward-thinking, as it was the first U.S. city to run entirely on renewable energy. It’s also popular for shopping, boating, eating, and drinking. 

Here’s what you should see and do:

  • Church Street Marketplace: The main pedestrian shopping street in Burlington that’s jam-packed with shops and restaurants.
  • Burlington Farmers Market: A local market held every Saturday where delicious produce, meats, and treats are sold.
  • Burlington Bike Path: A bike path with stunning views of Lake Champlain.
  • Pub crawl/brewery tours: Consider sampling the city’s renowned craft beer at places like Foam Brewers, Zero Gravity, and Switchback Brewing Company.
  • Lake Champlain: A large and pretty lake where you can partake in watersports, fishing, and boat cruises. Stay at a cabin overlooking this lake in VT; you’ll never want to leave!
The shores of Lake Champlain
Burlington straddles the shores of Lake Champlain.

Burlington, VT Is for Foodies

Be sure to give yourself plenty of time to indulge in Burlington’s culinary scene. It’s truly a foodie’s paradise, where you can find delicious food wherever you go. And it’s basically all organic and locally sourced, too. If you’re a dessert lover, Lake Champlain Chocolates is a must! And don’t even get me started on Vermont’s apple picking scene!

Also, if you have time (and a passport), head across the border to nearby Montreal and Quebec City.

Church Street in Burlington, Vermont
Church Street in Burlington, Vermont.

Alternative Northeast Road Trip in VT: Lake Willoughby

For one of the coolest Northeast road trip ideas imaginable, brace yourself for Lake Willoughby. Nestled in the heart of Vermont, it’s truly an adventure destination that will leave you speechless!

What makes Lake Willoughby a truly unique place to visit? Picture this: a pristine glacial lake cradled between towering mountains, as if Mother Nature herself had carved out this masterpiece. Majestic cliffs rise dramatically from the shimmering waters, casting mesmerizing reflections that dance across the surface. It’s like stepping into a postcard, but with the added bonus of feeling the crisp mountain air and hearing the serenade of nature all around you.

Lake Willoughby in New England
Whether you’re doing a New England summer road trip or a fall trip, Lake Willoughby is the place to be

Unique Experiences in Lake Willoughby

Lake Willoughby is an outdoor enthusiast’s dream. Hiking trails weave through the dense forest, leading you to awe-inspiring viewpoints that will leave you breathless. The area’s crown jewel is the Mount Pisgah Trail, a challenging yet rewarding trek with panoramic vistas of the entire lake and its surrounding glory. Trust me, the view from the top is worth every ounce of effort!

But that’s not all. Lake Willoughby beckons you to dip your toes in its crystal-clear waters. On a sunny day, you can rent a kayak or paddleboard to explore the lake at your own pace. Glide along the mirror-like surface, surrounded by the tranquility of nature.

Why Visit Lake Willoughby When Road-Tripping Through New England?

Vermont, with its picturesque landscapes and quaint towns, is a destination that belongs on every traveler’s bucket list. Lake Willoughby is the pièce de résistance. This hidden gem showcases Vermont’s raw beauty and offers a retreat from the hustle and bustle of everyday life. It’s a place where you can reconnect with nature, unwind, and let the stresses of the world melt away.

When autumn arrives in New England, Lake Willoughby transforms into a vibrant kaleidoscope of colors, painting the surrounding mountains with hues of gold, crimson, and orange.

So, if you find yourself embarking on a New England tour, make sure to include Lake Willoughby on your itinerary. Lake Willoughby is a destination that will steal your heart and leave you yearning for more. It’s easy to see why it’s one of my favorite places in the northeast!

Lake Willoughby Cabin
Beautiful cabin on the lake

Day 18: Manchester, Vermont

The next big bucket list item on this itinerary is the Berkshires in Western Massachusetts. It’s about 3.5 hours south of Burlington, so I recommend breaking up the journey by spending a night in Manchester, Vermont.

This quaint town is nestled in the heart of the Green Mountains. It’s known for its cozy inns and precious scenery. Consider checking out Stratton Mountain, Equinox Mountain, and Lye Brook Falls Trail, but don’t forget to relax and soak in the pastoral views, too.

If you’re willing to deviate a bit from this strictly New England road trip itinerary, consider stopping by Lake George and Saratoga Springs, New York, just over an hour away.

Scenic golf course in the green mountains on a sunny autumn day
The Green Mountains is a sought-after destination for seeing the fall foliage.

Days 19-21: The Berkshires, Massachusetts

The Berkshires is another must-see destination in New England. Situated in Western Massachusetts, this region spans from the border of Vermont to that of Connecticut. It hosts a variety of amazing outdoor activities, museums, and eateries. 

Here are some things you’ll want to see and experience in the Berkshires:

  • Downtown Stockbridge and Great Barrington: A pair of charming, New England towns in the heart of the Berkshires.
  • Mass MoCa Museum: A factory-turned-museum in North Adams that holds one of the largest contemporary art galleries in the U.S.
  • Hancock Shaker Village: A historic village built in the 1700s that sheds light on the rustic lifestyles of the Shakers (a Christian sect that is somewhat similar to the Quakers).
  • Norman Rockwell Museum: A museum dedicated to Norman Rockwell, an acclaimed American painter.
  • Whitewater rafting on the Deerfield River: A fun summer activity for adventure-seekers.
  • Mount Greylock State Reservation: Home to the tallest mountain in Massachusetts, Mt. Greylock (3,489 ft. – 1069 m). On a clear day, you can see five states from the top: Massachusetts, Vermont, New York, New Hampshire, and Connecticut.
  • Canoe or Kayak Tour: A peaceful way to experience the Housatonic River.
Nature in the Berkshires
Nature flourishes in the Berkshires.

Whether you’re into outdoor adventures, farm-to-table dining, or cool cultural sites, the Berkshires is a nice place to visit on a New England or Massachusetts road trip.

For more information on the Berkshires (especially during the fall foliage season), read my article: Fall in the Berkshires.

Hancock Shaker Village in the Berkshires
Hancock Shaker Village in the Berkshires.

Days 22-23: Connecticut Coast Scenic Drive, Connecticut

Though often overlooked by many New England visitors, Connecticut has no shortage of coastal cities and towns that make for the perfect summer road trip. For the full CT experience, stay in a cabin overlooking farmland and rolling hills or a cottage on the ocean.

Sheffield Island Lighthouse in Norwalk, Connecticut
Sheffield Island Lighthouse in Norwalk, Connecticut.

Begin this scenic coastal drive in Greenwich, near the New York state border, and head east towards Mystic and Stonington. It’s about a three-hour, 120-mile journey from one end to the other, but it’s well worth it for the sweeping ocean views. 

Here are some places you may want to stop along the way (ordered from west to east):

  • Greenwich: A coastal town steeped in rich history and culture. It’s one of the wealthiest communities in the country.
  • Fairfield: A college town with beautiful beaches, homes, and scenery.
  • Silver Sands State Park: Three miles of boardwalk through marshland, beaches, and sand dunes.
  • Branford: A town known for its expansive beaches and breweries. It’s also an excellent location for catching the sunrise.
  • Guilford: A historic town jam-packed with shops, restaurants, and parks.
  • Hammonasset Beach State Park: A 2-mile stretch of beaches in Madison, Connecticut.
  • Westbrook: A quaint community with sandy beaches and cozy B&Bs along the waterfront.
  • East Lyme: Home to Rocky Neck State Park, which contains over 700 acres of marshland, beaches, and rocky shorelines.
  • Mystic Seaport: A historic village with a unique maritime legacy. If you’re into gambling, consider spending a night at nearby Foxwoods or Mohegan Sun casinos.
  • Stonington: A beautiful seaside village and a good place to end your adventure along the Connecticut Coast Scenic Drive.

Once you make it to the end of this coastal drive, you’ll be within reach of the Rhode Island border.

Beautiful sunset over marsh with tall grass and trees in Connecticut Coast Scenic Drive
Connecticut Coast Scenic Drive is often glossed over on road trip itineraries through New England, but it shouldn’t be.

Day 24: Block Island, Rhode Island

Located off the coast of Rhode Island, Block Island is one of New England’s best hidden gems. It has the classic New England vibes of Martha’s Vineyard and Nantucket, without the crowds.

This island is steeped in pristine scenery and Victorian charm, hosting a variety of cool sights, including windswept beaches, historic lighthouses, and rustic farms.

The National Hotel on Block Island
The National Hotel is the flagship Victorian-era hotel on Block Island.

Interestingly, there are no stoplights or international chains on Block Island. It hasn’t changed all that much since the late-1800s, except for a few cars and electricity.

Many New Englanders visit Block Island as a day trip, but you can spend the night as well. To get there, take a ferry from any of the following places:

At this stage of your New England road trip, you’re probably ready for some R&R. There’s no better place to recharge your batteries than a secluded island getaway like Block Island.

The Mohegan Bluffs clay cliffs near the beach
The Mohegan Bluffs are clay cliffs that are about 150 feet high.

Days 25-26: Newport, RI

I recommend spending at least a day or two in Newport on your itinerary. It’s best known for its Gilded Age mansions built during the late 19th century. 

Here’s what you need to see:

  • The Breakers: The most iconic home in Newport. It was built as a summer residence for the Vanderbilt family, one of America’s wealthiest and most powerful families.
The Breakers mansion in Newport
The Breakers in Newport is about as lavish as a mansion can get.
  • Marble House: Another must-see mansion built from 500,000 cubic feet of marble.
  • Cliff Walk: A 3.5-mile walkway that connects many mansions with Newport’s scenic waterfront.
  • Rosecliff: An ornate mansion that was filmed in the 1974 film, The Great Gatsby.
  • Ocean Drive Historic District: A 10-mile scenic drive along the coastline.

Though Newport is a great place to spend a couple of nights, it’s also close enough to Boston for a day trip.

Rosecliff Mansion in Newport, Rhode Island
Rosecliff Mansion in Newport, Rhode Island.

Alternative New England road trip suggestion in RI: Providence

As the capital of Rhode Island, Providence is an up-and-coming destination you should consider when touring New England. The city is home to Brown University, one of the top universities in the world. Providence also boasts lively performing arts and restaurant scenes that are among the best in New England.

Stop by the Botanical Center at Roger Williams Park for a memorable visit. There’s also a zoo, museum, and planetarium here that offers plenty for an afternoon. Enjoy a beer at a local brewery and a meal at a top restaurant in the city. It’s not hard to see why Providence is a top Boston road trip.

Providence Rhode Island streets
Providence is among the best New England drives.

Days 27-30 Cape Cod, Massachusetts

I love Cape Cod. Since I was a kid, I’ve always enjoyed spending weekends there over the summer.

Take the Old King’s Highway (Route 6A), and you’ll pass by miles of scenic coastline paired with historic seaside villages. Continue on Rt. 6 all the way to Provincetown, which lies at the tip of the Cape. 

Here’s where you should visit along the way:

Lupines in Cape Cod
During the month of June, Cape Cod is a great place to see the lupines
  • Cape Cod Canal: A 7-mile canal that connects Cape Cod with the Massachusetts mainland. There’s a bike path that runs on both sides of the canal.
  • Sandwich Village: The oldest town on the Cape dating back to the 1600s. Here, you’ll find many historic homes and B&Bs. There are also popular museums like the Sandwich Glass Museums and Heritage Museums & Gardens.
  • Cape Cod Rail Trail: A bike trail that runs through Dennis, Harwich, Brewster, and Orleans.
  • Nickerson State Park: A campsite with pretty ponds and hiking trails. One of my favorite camping spots!

Here are some popular destinations that you should check out while you’re in Cape Cod:

  • Falmouth: A beach resort town in the Upper Cape with miles of beautiful shoreline.
  • Hyannis: A popular tourist destination that’s nicknamed the “capital of the Cape.”
  • Dennis: Another beach resort town worth checking out. Stay at a cozy cottage for an authentic local experience.
  • Chatham: I got married in this cute town. It’s definitely one of my favorite places on the Cape, and it’s very romantic to visit during the winter season!
  • Orleans: A beach town that faces the Atlantic Ocean and Cape Cod Bay. Experience the warm and cold water on both sides of the Cape.
  • Provincetown: A lively town known for its art and music scene. Here, you’ll find unique sights like Race Point Lighthouse, Race Point Beach, and Pilgrim Monument. There are many incredible lighthouses to choose from in this part of the Cape. Also, don’t miss Dune Shacks Trail, one of the top hikes in New England!
A beach in Provincetown
A beach in Provincetown, also known as P-Town. This is a must-see on a New England tour.

If you’re still looking for more to do on the Cape, try whale watching. Several whale watching cruises leave from Hyannis, Barnstable, and Provincetown. I did the Dolphin Fleet Whale Watch from Provincetown. It’s a must when you’re visiting the Cape.

Also, you can take a ferry to the nearby islands of Martha’s Vineyard or Nantucket. Both islands are hot getaways for the rich and famous. On Martha’s Vineyard, be sure to do your sightseeing aboard a moped!

Martha's vineyard with colorful gingerbread cottages
Martha’s Vineyard is known for these colorful gingerbread cottages.

Read next: 17 best vacation rentals in Cape Cod

Last Stop on this Road Trip Itinerary in New England: Plymouth, Massachusetts

Let’s wrap up this New England road trip by bringing it back to where it all began.

Plymouth, Massachusetts, was the site of the first Pilgrim settlement in 1620 (the town is celebrating its 400th birthday this year). There’s a rock left behind that marks the spot where the first settlers arrived, which is a bit underwhelming, but nevertheless worth seeing if you’re a history buff. Apparently, some of my ancestors arrived there on the Mayflower. Fun fact!

At a high-level, here’s a map showing this trip itinerary.

New England road trip map
New England road trip map.
Plymouth Rock
Plymouth Rock

Things to Consider When Planning Your New England Road Trip

Before you pack your bags and hit the road, there are a couple things to think through before leaving for 3-4 weeks.

Where to Start Your New England Road Trip

Embarking on a road trip through New England is exciting, but where should you begin this epic adventure? Sure, you can’t go wrong with cities like Portland (Maine) and Providence (Rhode Island), but Boston is the best starting point by far.

Boston, Massachusetts, is a perfect launching pad for your New England trip. As the region’s vibrant capital city, Boston offers a mix of rich history, cultural landmarks, and a lively urban atmosphere. It’s home to New England’s biggest and most accessible airport, Boston Logan International Airport, which has the cheapest rental cars.

PS: If you want to rent a car, I highly recommend Discover Cars to find the best rates!

Best Time of Year for a Northeast Road Trip

When planning a road trip through New England, timing is everything. Each season offers its own unique charm, so let’s explore the best time of year to embark on your adventure.

Spring brings a sense of renewal to New England, with blooming flowers and trees bursting with vibrant colors. However, remember that the weather can be unpredictable during this time. So pack layers and be prepared for rain showers (and even snow!).

Summer is when New England truly shines. The region’s coastlines come alive with beachgoers, and the warm weather invites you to explore the charming seaside villages and relax by the ocean. It’s also the perfect time for outdoor activities like hiking and kayaking. However, be prepared for larger crowds, especially in popular tourist destinations.

If you’re a fan of fall foliage, then autumn is the season for road tripping around New England. The region becomes a masterpiece as the leaves transform into vibrant shades of red, orange, and yellow. It’s one of the best places in the world for leaf peeping and apple picking.

Winter in New England has its own charm. If you love winter sports like skiing and snowboarding, the region’s ski resorts and mountainous landscapes will be your playground. Cozy up in a charming cabin and experience the New England wonderland when covered in snow. Be sure to check weather and road conditions, as winter storms can affect travel plans.

Two people enjoying a breathtaking view of a lake and mountains from a cliff in New England
My favorite New England road trips are in the fall (Sept and Oct)

Number of Days for a New England Road Trip

The number of days you’ll need for a road trip to New England depends on several factors. This includes your preferred destinations, the activities you want to engage in, and the pace you wish to travel. However, to fully immerse yourself in the region’s charm and explore its highlights, a road trip spanning at least 7 to 10 days is recommended.

During this timeframe, you can visit major cities like Boston, experience the coastal beauty of Maine and New Hampshire, venture into the picturesque towns of Vermont, and even include a visit to the stunning Acadia National Park. This duration allows for a balanced itinerary, giving you enough time to explore each destination.

If you have more time, extending your road trip to two weeks or even longer will allow you to delve deeper into the region. You can add additional stops, explore lesser-known gems, venture into the rural landscapes, or even consider taking a scenic detour to Cape Cod or Martha’s Vineyard.

Keep in mind that New England experiences distinct seasons, and the timing of your road trip will influence the activities available and the weather you’ll encounter. The summer and fall months are particularly popular due to pleasant weather, outdoor festivals, and the renowned fall foliage. However, each season has its own appeal…whether it’s spring awakening, winter wonderland activities, or the coziness of autumn.

Other Destinations to Consider When Road Tripping Through New England

If you’ve got more time and want to see more that New England has to offer, consider visiting these other cool places below:

  • Providence, RI: The capital of Rhode Island, home to Brown University, historic architecture, and a cool art and nightlife scene.
  • Woodstock, VT: A quaint town in central Vermont with historic buildings and beautiful scenery.
  • Lubec, ME: The easternmost town in the United States. Don’t miss the iconic lighthouse that hugs the shoreline!

FAQs About New England Road Trips

Here are some popular questions (and answers) about how to plan a New England trip.

What Does a 7 Day Trip Itinerary for New England Look Like?

If you only have a week to explore New England, here are the must-see stops you’ll want to see on a road trip:

  • Day 1: Start your road trip in Boston, Massachusetts. Explore the historic Freedom Trail, stopping at landmarks like the Paul Revere House and Faneuil Hall. Indulge in the city’s culinary scene with a dinner in the North End.
  • Day 2-3: Go to Acadia National Park in Maine. Hike along the scenic trails from the rugged coastline to the summit of Cadillac Mountain, where you can witness stunning sunrises and panoramic views. Bike ride along the carriage roads or explore the park’s lakes and islands by kayak.
  • Day 4: Travel along the picturesque Maine coast, stopping at towns like Camden and Rockland. Enjoy fresh seafood and take in the breathtaking views of the rugged coastline. Continue your journey to Portland and explore the Old Port district and visit the Portland Head Light.
  • Day 5-6: Cross into New Hampshire and head to the White Mountains region. Hike scenic trails like Franconia Ridge Loop or Mount Washington. Drive along the Kancamagus Highway. Visit the charming town of North Conway, known for its quaint shops and the Conway Scenic Railroad.
  • Day 7: Journey to Vermont and arrive in Stowe. Take in the breathtaking views of Mount Mansfield, Vermont’s highest peak. Explore the town’s quaint shops, sample local craft beer, or enjoy outdoor activities like hiking, biking, or skiing.
A picturesque church surrounded by vibrant fall foliage
Stowe is especially magical in the fall

How Can You See New England in 5 Days?

Looking for a 5 day road trip itinerary for New England? The best spots in the Northeast are spread out, so you won’t be able to cover it all. However, here’s an aggressive yet realistic itinerary to make the most of your time here:

  • Day 1: Arrive in Boston and explore the historic Freedom Trail. Visit landmarks like the Massachusetts State House, Paul Revere’s House, and the Old North Church. Check out Faneuil Hall Marketplace and indulge in an Italian meal in the North End.
  • Day 2-3: Drive north to Acadia National Park in Maine. Along the way, stop at the coastal town of Portland, Maine. Explore the Old Port district, and don’t miss Portland Head Light, one of the most iconic lighthouses in the region. Once you’re in Acadia, explore the scenic Park Loop Road and the Jordan Pond Path. Hike along the coastline, soak in panoramic views from Cadillac Mountain, and take in the beauty of Thunder Hole.
  • Day 4: Head inland to the charming town of North Conway, nestled in the White Mountains of NH. Drive along the Kancamagus Highway, stopping at picturesque overlooks and waterfalls. Explore the unique shops and boutiques in North Conway Village.
  • Day 5: Conclude your New England adventure with visits to Stowe and Burlington, Vermont. Explore the vibrant Church Street Marketplace, lined with shops and cafes. Walk along the waterfront of Lake Champlain and enjoy views of the Adirondack Mountains.

New England Road Trip Itineraries in 2024

Hope you enjoyed my guide on the Ultimate Road Trip Itinerary for New England! This should keep you busy for quite a while, and when you’ve tackled it all, feel free to check out these other New England articles for more inspiration:

Embark on an unforgettable journey through New England with this road trip
Enjoyed reading about this New England road trip? Pin it!

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Daniela June 22, 2020 - 16:55

You live in such a beautiful part of the country! Always enjoy reading your travel guides.

Global Viewpoint June 25, 2020 - 08:39

Thank you, Daniela! 🙂

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