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Quaint New England Towns: Road Trippin' USA

If you'd like some peace, culture, and stunning scenery in your next overseas adventure in the not-so-distant future, this road trip ticks all the boxes. Be transported back in time, as you travel through the stunning states of Massachusetts, New Hampshire, Maine, Vermont, Connecticut, and Rhode Island.

If you’d like some peace, culture, and stunning scenery in your next overseas adventure in the not-so-distant future, this road trip ticks all the boxes. Be transported back in time, as you travel through the stunning states of Massachusetts, New Hampshire, Maine, Vermont, Connecticut, and Rhode Island.

This “Quaint New England Towns” itinerary is a travel treat for all of your senses. Lose yourself in this road-tripping experience rich in culture, history, storytelling, and nature.

From museums to lakes, to vineyards and flower-adorned cottages by the sea, this charming trip will have you dreaming of new ways of being. So, say hello to quirkiness and curiosity as you roam freely through six uniquely different states.

Ready to go? Start planning now, ready for when international borders reopen soon.

Explore all of Brand USA’s 31 Amazing Self Drive Road Trip itineraries here.

Quaint New England Towns: Route Highlights


1. Boston, Massachusetts

Start your tour of Boston, Massachusetts at the Freedom Trail marker

You may already know all about Boston’s rich history and its role in the Revolutionary War, but you may not be aware of the city’s world-class museums, numerous universities, and abundant shopping opportunities.

Get ready to be ‘wowed’. Begin your adventure on The Freedom Trail, with its 16 historic stops, including the famous Old North Church and the Paul Revere House. Then, spend time enjoying the Museum of Fine Arts’ extensive collection or the eye-opening exhibits at the Museum of Science. If you’re after a more intimate experience, check out the Isabella Stewart Gardner Museum or the Nichols House Museum.

But wait… there’s more…

Walk, dance or skip across the Charles River on the Longfellow Bridge or take the “T” (subway) to Cambridge to explore the ivy-trimmed campus of Harvard University and pick up an iconic jumper from the Uni’s many bookstores.

Shopaholics should head to Newbury Street in the Back Bay, Copley Place, and the famous Faneuil Hall Marketplace, while sports fans tick off items on their bucket list, with a Boston Red Sox baseball game (April through October) and a tour of Fenway Park (AKA The Green Monster), the oldest Major League Baseball park in the country.

If the weather is nice, reconnect with the natural world by strolling through the Boston Common and taking a ride on one of the famous Swan Boats in the Public Garden.

2. Boston, Massachusetts > Kennebunkport, Maine

Kennebunk River, Kennebunkport

Head north along the scenic New England coast through Massachusetts. Infamous for the Salem Witch Trials of 1692, Salem is a colourful city with a rich maritime heritage, Victorian architecture, and fascinating stories that span nearly 400 years.

Then, continue through movie-famous Manchester-By-The-Sea, Massachusetts, and art-inspiring Rockport, Massachusetts, to Portsmouth, New Hampshire. Settled in 1623, Portsmouth’s historic past and cultural strengths make it an attractive destination, as well as being a gateway to New Castle, one of New Hampshire’s smallest towns and home of the Fort Constitution Historic Site.

After exploring the fort, depart for Maine, where your first stop is Ogunquit, named by the Abenaki tribe, meaning ‘beautiful place by the sea’. Enjoy the vintage feel of this town, stroll among quaint buildings or explore the Marginal Way ocean path.

Your final stop today is long-time shipbuilding centre, Kennebunkport, Maine, located along the Atlantic Ocean and Kennebunk River. Check out some of the fine mansions and maybe even stay at one!

  • DRIVE TIME: 144kms: 1 hour 30 mins drive time

3. Kennebunkport, Maine > Camden, Maine

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Megunticook Lake, Camden

First stop, Old Orchard Beach. Enjoy 11 kilometres of sandy beach and Old Orchard Beach Pier, stretching more than 150 metres over the Atlantic Ocean. Dreamy? We think so.

When you’ve had your ocean fix, continue north to the historic seacoast city of Portland (the Atlantic version that is!) with its funky galleries, one-of-a-kind shops, diverse restaurants, and many very photogenic lighthouses. Take time to explore the Arts District and Old Port historic district too.

As you drive through the mid-coast region of Maine, past quaint New England cottages and quiet coves, be sure to stop at Pemaquid Point Lighthouse in Bristol; it’s a fabulous photo spot!

Rockland, known as the ‘Gateway to Penobscot Bay’, is a classic working harbour town and home to galleries, craft shops, fine dining, and the Maine Lighthouse Museum. The final stop today is in Camden, where locals say ‘the mountains meet the sea’.

A culinary mecca, Camden features charming little streets, huge schooners, and locally owned art galleries, making it the perfect place to stop and explore at night.

  • DRIVE TIME: 174kms: 2 hours drive time

4. Camden, Maine > Bar Harbor, Maine

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Antique cannons decorating a public square, Bar Harbor, Maine

Everyone loves the beach, right? Today, follow the scenic shoreline of Penobscot Bay to Lincolnville in the heart of the Maine coast. This off-the-beaten-path place is a perfect spot to enjoy breathtaking views of the bay.

Next, visit the picturesque town of Blue Hill to enjoy a laid-back getaway. In addition to its historical architecture, Blue Hill is also a gateway to Acadia National Park.

Today’s final stop is Bar Harbor on Mount Desert Island, featuring elegant Victorian architecture, and situated between the blue waters of Frenchman Bay and the woodlands of Acadia National Park.

  • DRIVE TIME: 124kms: 1 hour 45 mins drive time

5. Bar Harbor, Maine > Bethel, Maine

Frenchman’s Hole, Bethel, Maine

Before travelling inland, take the morning to explore Acadia National Park, known for its rugged beauty. Expect to see glorious mountains and abundant wildlife, and hear the thunder of crashing waves; a perfect stop for some nature therapy.

Steep slopes rise above the rocky shore, including Cadillac Mountain, which at 465 metres is the highest peak on the U.S. Atlantic Coast.

When you’re feeling rejuvenated, travel east to Bethel, one of Maine’s popular mountain villages, and a hub of outdoor activities from skiing in winter to hiking and biking in summer.

  • DRIVE TIME: 294kms: 3 hours and 30 mins drive time

6. Bethel, Maine > North Conway, New Hampshire

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Black Cap Mountains, North Conway

Mountain lovers, get excited. Today, you can take a full day to explore the White Mountains of New Hampshire. First, travel to Gorham and join Highway 15 (Three Rivers Scenic Drive) which will take you past Mount Washington and the mountain pass known as Pinkham Notch.

If you’re feeling adventurous, stop to take the cog railway or drive to the summit of Mount Washington – known as ‘the home of the world’s worst weather’. Here, you can visit the weather station and Extreme Mount Washington museum. Outdoor enthusiasts won’t want to miss Pinkham Notch, a stunning natural landmark created by glaciers, erosion and rivers, and separating three mountain ranges. Choose to hike or relax on a Gondola ride and enjoy the views in Wildcat Mountain Ski Area.

Your day ends in North Conway in the heart of Mt. Washington Valley, home to nearly 100 stores, fine art galleries, locally made crafts, restaurants, pubs, and live entertainment. A wondrous place to base yourselves for the night.

  • DRIVE TIME: 80kms: 1 hour drive time

7. North Conway, New Hampshire > Londonderry, Vermont

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Robert Frost’s House, Londonderry, New Hampshire

From North Conway, explore more of the White Mountains, taking the scenic Kancamagus Highway, and grab a photo for the gram at Albany Covered Bridge along the way.

Next, stop at Flume Bridge on your way to spectacular Franconia Notch State Park with its walking trails, wildlife watching, and more.

Journey through Hanover, New Hampshire, home to Dartmouth College, and on to Woodstock, Vermont, which is full of quintessential New England charm. Then, continue to Londonderry at the gateway to the Green Mountains.

  • DRIVE TIME: 297kms: 3 hours and 15 mins drive time

8. Londonderry, Vermont > Stockbridge, Massachusetts

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Stockbridge, Massachusetts

From White Mountains to Green, explore the vivid colours of Vermont’s Green Mountains National Forest.

Enjoy pastoral views as you travel along Route 7a through Manchester and Bennington, Vermont, before arriving in North Adams, Massachusetts for lunch.

After you’ve tasted the delights of North Adams, continue to Stockbridge, home to the Norman Rockwell Museum, which boasts an extensive collection of the beloved American illustrator’s original works.

  • DRIVE TIME: 144kms: 1 hour and 45 mins drive time

9. Stockbridge, Massachusetts > Providence, Rhode Island > Mystic, Connecticut

Mystic, Connecticut

From Stockbridge, travel south to the Connecticut coast and Westport. The area offers some of the prettiest scenery in the state, making it a lovely stop for a picnic or a wander through town.

Further along the coast, check out Old Saybrook, famous for being the home of Katharine Hepburn. Filled with impressive architecture and many remarkable buildings, such as the Saybrook Breakwater Lighthouse, this is a perfect stop for lunch.

Continue on to Mystic. Aside from its amazing name, it’s an attractive seaside village with a rich heritage and home to the Mystic Seaport, one of the country’s largest maritime museums. Visit Main Street for many delicious seafood restaurants, quaint shops, and the famous Mystic Pizza restaurant.

  • DRIVE TIME: 200kms: 2 hours drive time

10. Mystic, Connecticut > Cape Cod, Massachusetts

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Highland Lighthouse, Cape Cod, Massachusetts

Time for another beach fix! Take Highway 1 to Narragansett, Rhode Island, known for its sandy beaches, and then take Highway 1a along the coast and across the Jamestown Bridge to Newport, one of the USA’s original playgrounds for the rich and famous.

Newport retains a luxurious feel and many of its Gilded Age mansions are open to the public for tours. If you are a tennis aficionado, take a trip to the International Tennis Hall of Fame in Newport before driving to beautiful Cape Cod, where today’s journey ends.

  • DRIVE TIME: 195kms: 2 hours drive time

11. Cape Cod, Massachusetts > Boston, Massachusetts

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Plymouth, Massachusetts

Cape Cod is the place to be! These charming beach towns could easily entertain you for several weeks or more, so do your research before your trip to determine what community best suits your style.

Choose from the bustle and fun of Falmouth, to the flower-adorned cottages of Orleans, the dune-swept beaches of Eastham and Truro, to busy Provincetown, an LGBT-friendly city boasting eclectic shops, galleries, and restaurants, as well as natural beaches and stellar whale watching.

The Cape’s scenic out islands – Martha’s Vineyard and Nantucket – can be reached via ferry or small plane.

After your visit to Cape Cod, drive to Plymouth, ‘America’s hometown’, where the Pilgrims landed in 1620 in search of a home and religious freedom.

Once you’re done exploring Plymouth, you can continue to Boston, where your quaint New England Towns road trip comes to a close.

  • DRIVE TIME: 113kms: 1 hour 15 mins drive time

Download the complete Quaint New England Towns itinerary here!’

Get the Road Trip Playlist

This playlist will have you car-seat-dancing and singing into your hairbrush to the sweet sounds of Tim McGraw, Cheryl Wheeler, Frank Sinatra, Billie Holiday, and more.

With songs dedicated to these destinations, you’ll be in the mood to explore, even more, after the delightful musical melodies of this whimsical playlist.

Agents: Download, Escape and Explore GoUSA TV

GoUSA TV is a free premier travel entertainment channel. Watch full episodes, documentaries and films, told from the diverse perspectives of real people across America. 

With more than 400 authentic and short format videos featuring destinations from all 50 states, 5 territories, and the District of Columbia, there’s never been a better time to get online and enjoy some incredible travel entertainment!

Available for download in the App or Play store and on Apple TV.

More info here.

Agents: Join the USA Discovery Program

Stockbridge, Massachusetts

The USA Discovery Program is Brand USA’s official trade training platform for the USA. The Quaint New England Towns itinerary features two destinations with training badges.

Get clicking and complete your Massachusetts and Rhode Island badges and get all the knowledge in a fun and interactive way.

Click here to register and get all the knowledge for the USA.

PLUS! Design your own Road Trip with the USA TRIP PLANNER

The Visit USA Trip Planner is an amazing (and free!) tool that matches your personal travel preferences and style.

With over 230 million data points including the best places & times to visit, reviews and hidden gems, this is one smart piece of travel tech.

This little travel genius optimises your itinerary to minimise travel time, checks when attractions are open and even recommends how much time to spend at each stop off. Brilliant!

Finally, it lets you share & collaborate with your fellow road trippers and is easy to add or revise points of interest as you go.

Find out more: Trip-Planner.VisitTheUSA.com

Get all the tools on Brand USA’s TRAVEL TRADE SITE


From Trip Planners to Itineraries and the USA Discovery Program and Destination information, Brand USA’s Travel Trade Site for agents has you covered.

Hero image – North Conway, New Hampshire

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