The prettiest small towns in New England

Indulge us as we dedicate a short (and sweet) love letter to New England: Home of lobster rolls, Emily Dickinson and, of course, some of the most idyllic small towns in all the land, a road trip through Maine, New Hampshire, Vermont, Massachusetts, Connecticut and Rhode Island is 100 percent worth it. Here, 11 of the cutest spots that should definitely be on your list.

The prettiest small towns in New England
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The prettiest small towns in New England

Woodstock, Vermont

It’s no surprise that most of the buildings in this tiny (and quintessential) New England town—founded in 1787—are on the National Register of Historic Places. Located in the Green Mountains, the town boasts just about 3,000 residents, plus plenty of things to do and see, from perusing the Woodstock Farmers’ Market to catching live music at the Woodstock Town Hall Theatre.


Bristol, Rhode Island

The vibes are chill in this seaside town—so chill that you could actually commit to getting around without a car. (The East Bay Bike Path kicks off here and you can ride it all the way to Providence.)


Stockbridge, Massachusetts

Um, Norman Rockwell used this town in the Berkshires as inspiration for his work. That is all.


Bar Harbor, Maine

This town offers ocean views and artisanal (and adorable) ice-cream shops. Plus, you’re a hop, skip and a jump hike away from Acadia National Park.


Exeter, New Hampshire

Sure, it’s home to the infamous private school (Phillips Exeter Academy), but it’s also home to an assortment of mom-and-pop shops, restaurants, art galleries and some of the best foliage you’ll ever Instagram.


Concord, Massachusetts

The first shots of the Revolutionary War were fired here. Add to that the fact that some of the most cherished American literary figures—Ralph Waldo Emerson, Louisa May Alcott and Henry David Thoreau—all lived (and felt inspired) here at one point. Note to self if you visit: Do not skip Walden Pond.


Newport, Rhode Island

Yes, the mansions—like the Breakers—are epic. But so are the sunsets, the coastal walkways and all the charming (regular-sized) homes.


Sugar Hill, New Hampshire

There are approximately 500 year-round residents in this quaint little town, nestled on the edge of the White Mountains. But the local country store makes its own cheddar from scratch, so there’s that.


Camden, Maine

Right on the edge of Penobscot Bay, this postcard-perfect seaport has it all—mountain views, delicious seafood nearby and (made in Maine) wine.


Edgartown, Massachusetts

OK, so you have to take a short ferry ride to visit this super-cute Martha’s Vineyard town, but it’s worth the trip to see the old whaling port, bustling with old-school Americana and celebrity sightings. (We’re talking about you, Barack Obama.)


Washington, Connecticut

It’s what the fictional town of Stars Hollow from Gilmore Girls is based on. Enough said.



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