7 New England Towns With Unforgettable Main Streets
New England is one of the most photogenic parts of the United States, known for its postcard towns where time seems to slow down. Brick-lined Main Streets are a hub for the creative community with their historic venues and artisan shops. In towns where the population stays below 50,000 people, the magic of small-town life lives on, as you can learn history, shop for antique goods, and try local produce in the same place. From coastal villages to mountain enclaves, these seven New England towns offer the kind of Main Streets that are worth a trip on their own.
Great Barrington, Massachusetts
Great Barrington is one of the most scenic towns in the Berkshires in Massachusetts, with a population hovering around 7,000. The Downtown Great Barrington Cultural District is home to a thriving art community, as well as historic and culinary venues. The Mahaiwe Performing Arts Center is a restored theater whose name comes from the indigenous Mohican term for "the place downstream," a reference to the Housatonic River.
A few doors down, Fuel Coffee is the community's informal living room, with excellent espresso and walls decked in quirky art. Yellow House Books offers a selection of used fiction and nonfiction that rivals a big urban shop. This town is the center of a wide array of cultural and recreational opportunities in the Southern Berkshires.
Woodstock, Vermont
Located in the heart of New England, Woodstock is a town of 3,000 people that looks like a painting come to life. Its Main Street is lined with 18th-century buildings, local shops, and inviting restaurants. One of the most prominent businesses along this drag is F.H. Gillingham & Sons General Store, which has been selling classic Vermont goods like maple syrup, cookies, and jams for 130 years. Another can't-miss shop in the area is Woodstock Scoops, where you can sample Vermont’s farm-to-cone soft-serve ice cream and a variety of milkshakes.
If you want to stay in the heart of town, book a night at the Woodstock Inn & Resort, an iconic hotel that offers a down-to-earth New England welcome. Don't miss out on Norman Williams Public Library, the town’s cultural center, or check out the Middle Covered Bridge, which stretches over the Ottauquechee River and is one of the most popular photo stops in Woodstock.
Camden, Maine
Just three-and-a-half hours from Boston, Camden is a lively coastal village that makes for a fun New England getaway. Located at the foot of Camden Hills on Penobscot Bay, Camden boasts 19th-century architecture and unmistakable New England charm with boats moored in the bay and small waterfront restuarnts serving seafood. Camden’s Main Street is a lively passage where you can catch a show at the Camden Opera House, a carefully restored 1894 venue that brings live music, film, and theater to the heart of town.
There are plenty of places to grab a bite too. Long Grain is a celebrated restaurant tucked slightly off Main Street that serves tasty Thai cuisine, such as homemade noodles, stir fry, and rice. Need a few presents for your friends and family? Check out The Smiling Cow, a family-owned gift shop, a staple of Camden for over 75 years, that sells homemade fudge, maple syrup, and various trinkets. Whether you want to enjoy Harbor Park, where schooners bob on the water, admire Mount Battie in the distance, or catch a boat ride along the harbor, you will understand why Camden is called “the Jewel of the Maine Coast.”
Brattleboro, Vermont
Brattleboro is a town in Southern Vermont known for its independent spirit and recreational scene. It also has deep cultural roots which you can see in many local institutions such as Brattleboro Museum & Art Center and Latchis Theatre. While art and performance are big in Brattleboro, the main drag also offers plenty of commerce.
Brattleboro’s Main Street is home to quirky local shops and cultural establishments like the Brattleboro Food Co-op, a community-owned store that perfectly exemplifies the state's commitment to sustainable, local food. Just up the street, you can find Everyone’s Books. This indie shop has a remarkable selection of literature, social justice titles, and other genres in a welcoming and creaky-floored space. The nearby River Gallery School of Art is a perfect stop for curious visitors, as it combines art education with public engagement.
Mystic, Connecticut
Once a shipbuilding hub of the East Coast, Mystic offers a rich maritime history and an old drawbridge in the heart of town. Hosted by the Mystic Seaport museum, the Charles W. Morgan is the last wooden whaleship still afloat in the U.S. and a recollection of items. Make sure also to check out the rest of the museum, which hosts permanent and rotating exhibits from the town's shipbuilding past.
A visit to Mystic Drawbridge Ice Cream at the foot of the famous Mystic River Bascule Bridge is a rite of passage, especially in summer when tourists come here for artisan ice cream while the bridge slowly lifts for passing sailboats. For readers, Bank Square Books is a cozy independent bookstore that frequently hosts writers for book readings and signings. Lighthouse Bakery is a perfect stop for some freshly brewed coffee and pastries. A quiet walk toward the end of Main Street brings you to Mystic River Park, a waterfront spot where you can catch your breath and watch paddleboarders glide by.
Newburyport, Massachusetts
Newburyport is a small town north of Boston known for its shipbuilding history. A hometown of the prominent abolitionist William Lloyd Garrison, Newburyport is also where the U.S. Coast Guard started. Located on the southern bank of the Merrimack River, it boasts a classic brick-lined Main Street with many locally owned shops and eateries.
A trip to Newburyport isn’t complete without a stop at The Tannery Marketplace, which was called the best shopping spot on the North Shore by Boston Magazine. A short walk from Main Street, this area is home to artisan shops, yoga studios, and a farmers market. Back on Main, Joppa Fine Foods is a lunch restaurant offering cheeses, charcuterie, and specialty imports, perfect for trying classic New England produce. The Old South Presbyterian Church, built in 1756, is an ideal backdrop for your photos. If you have more time, don’t miss the Custom House Maritime Museum, which served as a customs house when Newbury was a major port and offers a glimpse into local history.
Exeter, New Hampshire
A former revolutionary capital of New England, Exeter was a seaport in the late 1600's and early to late 1700’s. No visit is complete without a stop at the American Independence Museum, inside the Ladd-Gilman House, a National Historic Landmark. The museum is home to an original printed copy of the Declaration of Independence and thousands of artifacts from the American Revolution.
Downtown Exeter boasts a vibrant community spirit and scholarly influence, thanks to Phillips Exeter Academy, an independent college-preparatory school and one of the oldest boarding schools in America. Start your tour of the area with a stop at Water Street Bookstore, an independent bookseller with thoughtfully curated shelves and frequent events. Then, wander over to Exeter Bandstand, a community hub that offers a chance to catch a peaceful moment and reflect on the town’s deep historical roots.
Final words
New England’s small towns are the best spots for finding local charm. It’s in these walkable towns where Main Street still matters. Whether you're watching sailboats in Mystic, browsing books in Brattleboro, or catching a show in Camden, each has a unique story. New England’s Main Streets are a reminder that the best experiences come from slowing down, looking around, and enjoying an unhurried small-town atmosphere where history and community intersect on every corner.
