Itinerary – Quaint New England Towns
Massachusetts, New Hampshire, Maine, Vermont, Connecticut, Rhode Island

Regional Experiences Boston | Kennebunkport | Camden | Bar Harbor | Bethel
North Conway | Londonderry | Stockbridge | Mystic | Cape Cod

About this itinerary

Driving distance: 1,216 Miles
Recommended travelling time: 21 Nights
Recommended travel season: Fall or Summer
Explore the six states that make up New England. This itinerary covers everything from iconic cities, to quintessentially American towns, from stunning coastlines to the great outdoors! There really is something for everyone.

Boston, Massachusetts to Kennebunkport, Maine


Discover the treasures of Boston's world-class museums, universities, and abundant shopping opportunities. Explore The Freedom Trail with its 16 historic stops or enjoy the Museum of Fine Arts' extensive collection. Then head north to Salem, a vibrant city infamous for its witch trials; Rockport; Portsmouth; and quaint New Castle, home of the Fort Constitution Historic Site. In Maine, Ogunquit, or 'beautiful place by the sea', is well worth a stop. Explore the pretty town and its Marginal Way ocean path. Finally, visit Kennebunkport, Maine, settled in the 1600s, some of the historic mansions are now cozy inns.
Length of leg: 139 miles | Total distance travelled: 139 miles


Kennebunkport, Maine to Bar Harbor, Maine

Heading out of town, visit Old Orchard Beach before exploring the eclectic galleries, shops, restaurants and lighthouses in Portland. Then, stop at Pemaquid Point Lighthouse and Rockland, known as the 'Gateway to Penobscot Bay', a classic harbour town. Overnight in Camden, a treat for any foodie. The next day, follow the Maine coast from Penobscot Bay to Lincolnville, a hidden gem with breath-taking views. Journey onto Blue Hill with its historical architecture and shipbuilding roots before staying in Bar Harbor on Mount Desert Island, an elegant town in the heart of Frenchman Bay and the nature of Acadia National Park.
Length of leg: 212 miles | Total distance travelled: 351miles

Bar Harbor, Maine to North Conway, New Hampshire

Explore Acadia National Park, an area of outstanding natural beauty, with glorious mountains and abundant wildlife both in the park and along the coastline. Travel west to Bethel, one of Maine's popular mountain villages, and try out winter and summer outdoor activities. Take a day to explore the White Mountains of New Hampshire, travelling to Gorham on the stunning route past Mount Washington and the Pinkham Notch mountain pass, which separates three mountain ranges. Enjoy the views on a hike or a Gondola ride. Overnight in North Conway, the heart of Mt. Washington Valley, home to a wide variety of shops, galleries and restaurants.
Length of leg: 232 miles | Total distance travelled: 583 miles


North Conway, New Hampshire to Stockbridge, Massachusetts

From North Conway explore the scenic Kancamagus Highway enjoying the trails, aerial tramway and delightful wildlife of the spectacular Franconia Notch State Park before journeying through Hanover, home to Dartmouth College, and on to Woodstock, a charming town. Continue to Londonderry, the gateway to the Green Mountains, a delight for nature lovers all year round, but especially in autumn. Drive Route 7a through Manchester and Bennington, looking for the iconic covered bridges en route. Stop at North Adams for lunch and continue to Stockbridge, home to the Norman Rockwell Museum, with its impressive collection of the American illustrator's original works.
Length of leg: 253 miles | Total distance travelled: 836 miles

Stockbridge, Massachusetts to Cape Cod, Massachusetts

From Stockbridge, travel south along the coast to Westport and see the pretty red brick buildings before stopping at Old Saybrook, the home of Katharine Hepburn. Continue onto the little seaside village of Mystic, whose rich history is preserved at the Mystic Seaport Maritime Museum, and enjoy the fresh seafood on Main Street! Take Highway 1 to Narragansett known for its sandy beaches, and then head along the picturesque coast to the Jamestown Bridge where you will cross into glamourous Newport with its Gilded Age mansions and the International Tennis Hall of Fame. Overnight in the charming Cape Cod.
Length of leg: 308 miles | Total distance travelled: 1,144 miles


Cape Cod, Massachusetts to Boston, Massachusetts

There's no shortage of beach towns along the shores of Cape Cod and you're sure to find the perfect match depending on what you are looking for. Be sure to also visit the islands of Martha's Vineyard and Nantucket. Visit in spring or autumn if you can to avoid the summer crowds. From here drive to the original town of America, Plymouth, where the Pilgrims landed in 1620. Then head to Boston and finish your trip at Fenway Park to see a Boston Red Sox baseball game or take in the iconic Harvard University with its nearby cafés and bookstores.
Length of leg: 72 miles | Total distance travelled: 1,216 miles

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Some map icons by Scott de Jonge, used under CC 3.0 BY  Train vector by Freepik

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