Road trip through New England and you’ll find bustling cities, wild forests, and rolling fields, but the region’s small towns offer a unique experience of northeastern history and culture. In some of these communities, votes are still taken by a chorus of “ayes” and “nays,” and locals get their gossip while stopping by the country store or fishing pier. It’s not that New England small towns are frozen in time—the gossipers are likely organic farmers, chefs, and artists with global roots. But for locals and visitors alike, these towns offer a chance to slow down, unwind, and enjoy a slice of country life, Yankee style.

downtown Litchfield buildings at sunset

Litchfield, Connecticut. Photo © JMabel, licensed CC BY-SA.

Litchfield, Connecticut

Set in the idyllic Litchfield Hills, there’s handsome, 18th-century architecture clustered around Litchfield’s pretty town green. You can visit the one-room law school that was the first founded in America, bring a picnic to Topsmead State Forest, or join a crowd of New York City escapees for lunch in the stylish West Street Grill.

Little Compton, Rhode Island

In the shadow of Newport’s Gilded Age glamour, this coastal community exudes quiet charm with none of the flash. The town green is on the National Register of Historic Places, and artists line up along the water to paint scenes of the rocky beach. Spend an afternoon by the water, then stop into The Common’s Lunch for a bowl of creamy chowder or a slice of blueberry pie. Chicken lovers take note: a village in Little Compton is the home of the Rhode Island Red, a heritage breed that’s also Rhode Island’s state bird.

view of the island of Nantucket from the water

The sand island town of Nantucket. Photo © j76n/iStock.

Nantucket, Massachusetts

The Algonquin name for this tiny sand island meant “faraway land,” and though it’s just 30 miles from the tip of Cape Cod, it still feels like a place apart. On warm, summer days when bloom along cobblestone streets, locals meet up to “go laning,” their term for a leisurely stroll through Nantucket’s back alleys. To enjoy the perfect day in the town of Nantucket, learn about the heyday of New England’s whalers at the Nantucket Whaling Museum, hop a sailing tour along the coast, or rent a bike for a trip to the beach.

yellow New England house with roses and a picket fence

Picturesque house in Woodstock, Vermont. Photo courtesy of the Vermont Department of Tourism and Marketing.

Woodstock, Vermont

This picture-perfect village clusters around a cozy town green, where local news is posted on the old-fashioned “town crier,” a notice board for lost pets, traditional contra dances, and tractors for sale. The Quechee River flows right through the heart of town, ducking under a red-painted covered bridge with exposed trusses, and there’s always animals to pet at the nearby Billings Farm & Museum.

Hancock, New Hampshire

A white-steepled church and a tidy town green give Hancock’s center a classic New England feel, and a Revere & Sons bell still chimes in the town meetinghouse tower. Hancock is a quiet taste of rural life in southern New Hampshire, but on sunny, summer days, it fills with hikers on the way to Mount Monadnock, a rocky peak that’s often called “the most climbed mountain in America.” The award for best pre- or post-hike snack in Hancock goes to Fiddleheads Café, with hearty breakfasts and flatbreads.

sunshine over Rockland lighthouse

Rockland Breakwater Lighthouse. Photo © vagrant83/iStock.

Rockland, Maine

With the salt air and grit of a working fishing town, Rockland’s kept in touch with its maritime past even as the main street filled with art galleries, cozy cafes, and colorful shops. See art from three generations of Wyeths at the Farnsworth Museum, walk across the harbor to the Rockland Breakwater Light, then duck into Fog Bar and Café for a locally-brewed beer and Maine seafood.


Ready to hit the road? Plan your travel with more detailed itineraries and maps in Moon New England Road Trip.