10 New England Small Towns Loaded With Charm

Postcard-ready, quaint small towns for the perfect vacation? New England has them in spades.

The old New England—that land of the stacked-stone field walls and little red-brick downtowns nestled in the hills or tucked in beside historic wharves where schooners once docked—it still exists once you depart the urban centers. Past dairy farms and old mills, past fields with Revolutionary War history, you find these quaint towns—little communities that still carry that dream of New England you've had in your head.

Best of all, with a backdrop of rolling hills, soft mountains or the sea, these little towns often beckon for summer and fall vacations—especially fall, when peak leaf season rolls down the East Coast. To help you chase that dream, we've picked 10 of the best New England towns, but don't let our list stop you from exploring more. That little two-lane blacktop road with a sign noting another town 12 miles away? Follow it, and make your own story.


Mystic, Connecticut

Mystic, Connecticut

Anyone who has seen the 1988 film "Mystic Pizza," which introduced the world to Julia Roberts, got a small glimpse of this coastal Connecticut town. "Mystic Pizza (the restaurant) is still slinging slices of heaven from its nostalgia-inducing downtown location," said Leigh Harrington, Boston editor for Where. Pizza, of course, isn’t all there is to Mystic. The Mystic Seaport maritime museum brings the country’s early seafaring history to life with a re-created 19th-century coastal village, working shipyard and costumed interpreters. Downtown, travelers can traverse Bascule Bridge over the Mystic River to shop at more than 80 locally owned boutiques. 


North Adams, Massachusetts

North Adams

The arts define Massachusetts’ Berkshires region, which is where this former mill town sits. North Adams’ biggest claim to fame is the Massachusetts Museum of Contemporary Art, a 16-acre indoor-outdoor contemporary art museum and complex that presents thought-provoking and boundary pushing visual and performing artists. Accordingly, art galleries and artist studios are spread across this small city. Its location in the northwest corner of the Berkshire Mountains puts North Adams atop many travelers’ list of fall foliage destinations. In fact, since 1955 the town has been home to a weeklong Fall Foliage Festival and Parade.


Block Island, Rhode Island

Block Island

This island off the coast of Rhode Island might be small, but it is big on charm. About a thousand people live on Block Island’s 9.7 square miles, and about 40 percent of the island is set aside for nature conservation. "Visiting Block Island is a step back in time," said Jessica Willi, executive director of the Block Island Tourism Council. "It is a quaint community where the locals know one another and always stop to wave and chat." Adding to the charming allure is the fact that there are no franchise stores or restaurants on Block Island. Numerous shipwrecks around the island are popular destinations for divers. 


Wolfeboro, New Hampshire

Wolfeboro

Wolfeboro has flourished as a popular summer resort for well-to-do families from Boston and southern New England since the 1850s. The town of about 6,000 residents surrounds Lake Wentworth and is on the shore of the larger Lake Winnipesaukee, giving residents and visitors plenty of water activities to keep them busy. Mary DeVries, the executive director of the Wolfeboro Area Chamber of Commerce sums up the town’s charm this way: "You can sit in the park or stroll along dockside enjoying beautiful views of the lake and easily meander over to the locally-owned shops and restaurants." 


Camden, Maine

Camden, Maine

South of Bangor, Camden calls to travelers looking for a quiet, summer weekend escape. Five minutes from town center, Camden Harbour Inn is the place to stay, Harrington said, with such flourishes as gourmet local chocolates at turndown, in-room wood-burning fireplaces and a complimentary a la carte champagne breakfast at its AAA Four Diamond restaurant. "Upscale gift boutiques and art galleries cater to well-heeled customers, but there are a few shops that also wear kitschy lobster T-shirts and souvenirs like a badge of honor." In winter, go skiing at the Camden Snow Bowl, the only ski resort on the East Coast with ocean views.


Exeter, New Hampshire

Exeter

Founded in 1638 along the Squamscott River, Exeter takes great pride in its history. At the American Independence Museum, visitors can tour the Ladd-Gilman House, which was the state treasury during the American Revolution, and the annual Revolutionary War Festival is held on the museum grounds. Tree-lined Water Street, Exeter’s main road, is full of small shops and restaurants. Ramping up the charm factor is the bandstand at the center of town, where the oldest, continuously organized brass band in the country (founded in 1847) performs during the summer.


Boothbay Harbor, Maine

Boothbay Harbor, Maine

"At the reaches of Maine where the coastline looks like it’s been torn to shreds and poorly pieced back together, Boothbay Harbor is a blue-collar fishing town turned seasonal destination," Harrington said. Worthy attractions on the peninsula include Coastal Maine Botanical Gardens—"especially if you have little girls wanting to build fairy houses," she noted—and any variety of harbor cruising and kayaking tours. More than 200 artists call the area home—that’s a big portion of Boothbay Harbor’s 3,000 residents. Most visitors stay in small inns and vacation rentals; hotels are fairly limited. 


Weston, Vermont

Weston

You couldn’t write an ode to small-town charm any more perfect than Weston. The town, which is less than a two-hour drive northeast of Albany, New York, has fewer than 600 residents, and a tree-lined town square is home to a traditional bandstand where concerts are held. Jim Linville, the vice chairman of the Weston Selectboard, said one of Weston's most-charming stops is the Vermont Country Store, which is now operated by third-generation store owners. Then there's the Weston Playhouse Theatre Company, founded 80 years ago and "still producing a remarkable number of high-quality, professional productions." 


Montpelier, Vermont

Montpelier

Yes, Montpelier is Vermont’s capital. But don’t let that fool you; it is still a small, charming New England town (at about 8,000 people, it is the least-populous state capital in the U.S.). As you would expect from the home of the New England Culinary Institute, there is a variety of amazing restaurants, many of which deliver farm-to-table cuisine. Talk about charm: The front lawn of the State House fills up most evenings with people eating picnics, enjoying fellowship and throwing Frisbees. 


Rockport, Massachusetts

Rockport

North of Boston on Cape Ann, Rockport boasts a history that intertwines art and fishing. Some say that the rocky seaside town’s "magical light” draws painters here, Harrington said, "particularly in the 1930s, but whatever the reason, they’ve come—Winslow Homer, Fitz Hugh Lane, Childe Hassam, Edward Hopper and the like." Today, the arts still thrive at the Cape Ann Museum and at art galleries—especially those galleries on Bearskin Neck, a quaint stretch of old lobstermen and fishermen shacks converted into a row of restaurants, shops and galleries.

Dustin Turner
About the author