11 Most Charming Small Towns in New England

With appealing downtowns from the coast to the mountains, New England has some of the prettiest small towns in the USA.

Red, orange, and green autumn foliage, along country road with two houses in Woodstock, Vermont

Woodstock, Vermont, was established 15 years before the United States.

Photo by Wirestock Creators/Shutterstock

Small-town life takes on a new meaning in New England. In this region of six states—Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont—the streets have histories that are rooted in the country’s colonial past, with many of the buildings and streets boasting the same facades from hundreds of years ago. The mountains, bays, and forests of this region also can offer a much-needed respite from the chaos of city life.

Whether you’re coming for summer getaways by the Atlantic or road trips dedicated to foliage in the fall, these are the 11 best small towns in New England.

1. Woodstock, Vermont

Woodstock, Vermont, is a historian’s dream. Many buildings in this 1761-founded town are on the National Register of Historic Places, including former president Calvin Coolidge’s childhood home and the pink sandstone Norman Williams Public Library. Don’t miss one of the town’s picture-perfect landmarks, the Middle Covered Bridge, which stretches across the Ottauquechee River in the heart of Woodstock. The trails and historic buildings of the Marsh-Billings-Rockefeller National Historical Park are another way to explore the small town’s natural landscape and sights like the Belvedere Complex.

Looking to stay nearby? Reserve a room at the upscale Woodstock Inn & Resort in Woodstock’s downtown, which comes complete with a golf course and saunas.

White church with high steeple in Williamstown

Williamstown is also home to the Williamstown Theatre Festival, one of the biggest theater festivals in the country.

Photo by Albert Pego/Shutterstock

2. Williamstown, Massachusetts

Williamstown, Massachusetts, has been a well-known stop for road-trippers passing through the 63-mile Mohawk Trail. Besides being home to Williams College and events like the Williamstown Theatre Festival, the town is most associated with fall foliage visits from mid-September to mid-October, and nearby North Adams hosts a parade on the first Sunday of October celebrating the changing leaves. Try the 11.2-mile Ashuwillticook Rail Trail and Mount Greylock for the best views of the changing leaves.

Staying the night? Check out Tourists, opened in 2018 in in North Adams, a boutique hotel that combines minimalist and rustic elements with high-vaulted ceilings, wood detailing, and neutral-colored furniture.

Fishing boats of different colors docked in Perkins Cove, Ogunquit on a sunny day

Many restaurants, galleries, and hotels in Ogunquit are owned by members of the LGBTQ+ community.

Photo by haveseen/Shutterstock

3. Ogunquit, Maine

Eating delicious lobster on Maine’s coast isn’t reserved for the summer, as Ogunquit proves. After the summer peak crowds clear the region, AFAR contributor Suzanne Rowan Kelleher suggests heading to lobster spots like Barnacle Billy’s, Lobster Pound, and the Oarweed—all of which stay open well into the fall. And the festivities don’t end when winter rolls around. Its annual Christmas by the Sea celebration is a great time to explore its small-town charm, whether through a gallery tour, a choral concert, or an arts-and-crafts showcase.

 Saco River in Conway, New Hampshire, surrounded by fields and trees, with mountains in background

Conway is near the Saco River.

Photo by Jon Bilous/Shutterstock

4. Conway, New Hampshire

On the border of New Hampshire and Maine, Conway is a pocket of small-town life among the striking peaks of the White Mountains. The 34.5-mile Kancamagus Highway, which ends in Lincoln, New Hampshire, starts in Conway and provides fantastic vistas of changing leaves as it cuts through White Mountain National Forest. Seeing the area’s nature is perfectly doable by train, too: Drive 10 minutes and admire the Crawford Notch pass on the Conway Scenic Railroad Mountaineer from North Conway to Fabyan, New Hampshire.

If you’re up for a challenge, drive an hour north and hike the 18-mile Presidential Traverse Trail; be prepared to scramble up some rocks on this hike.

A few small boats in water by shore of Provincetown beach

The Mayflower first landed in Provincetown before landing in Plymouth, Massachusetts.

Photo by lunamarina/Shutterstock

5. Provincetown, Massachusetts

More than 400 years ago, the Mayflower ended its 66-day voyage from England, first stopping at what is now Provincetown, Massachusetts, before continuing along to Plymouth. During the summer high season, hordes of tourists head to the destination via Old King’s Highway in Cape Cod (aka Historic Route 6A), passing through cranberry bogs and salt marshes along the way.

This town on the northern tip of Cape Cod has been a longtime haven for artists (it’s actually America’s oldest continuous art colony), evident in spaces from the town’s Friday night Gallery Strolls to the Provincetown Art Association and Museum. The town is also popular for those in the LGBTQ+ community with several events hosted throughout the year: Its week-long Trans Week (previously known as Fantasia Fair) is the longest-running transgender conference in the world.

River lined with old buildings in Westerly, Rhode Island

Westerly, located in Washington County, was first settled in the 17th century.

Photo by digidreamgrafix/Shutterstock

6. Westerly, Rhode Island

Despite Rhode Island’s nickname as the Ocean State, the state’s more than 400 miles of coastline tend to be overlooked in favor of spots in Maine or Massachusetts. But Rhode Island’s southernmost town is worth a stop for its small-town-meets-beach atmosphere. Its three-mile-long Misquamicut Beach and Watch Hill Beach are swoonworthy (the latter has captured the heart of Taylor Swift) and has a vibrant downtown filled with local shops and boutiques.

For a place to rest your head, arguably no stay beats the luxury of the Ocean House Hotel, a Victorian property that sits on Watch Hill.

Exterior of Mystic Seaport, outdoor re-created 19th-century village and educational maritime museum, with masted ship

Mystic’s history with shipbuilding goes back more than two centuries.

Photo by Faina Gurevich/Shutterstock

7. Mystic, Connecticut

Julia Roberts and co. made Mystic, Connecticut, famous with the 1988 romantic comedy movie Mystic Pizza. The movie portrays a seaport town characterized by slow living, and 35 years later, this idyllic spirit remains intact in this town of slightly less than 5,000.

Take in the town’s nautical roots at the Mystic Seaport Museum; exhibits that focus on maritime history include figureheads and shipcarvings. You can reimagine life alongside woodcarvers and riggers in the 1800s by visiting the museum’s re-created 19th-century Seaport Village.

Aerial view of small-town Stowe, surrounded by trees in fall foliage

Stowe, Vermont, is near Mount Mansfield.

Photo by marchello74/Shutterstock

8. Stowe, Vermont

Stowe attracts skiers and snowboarders to the 4,393-foot Mount Mansfield (Vermont’s highest peak), making it one of the premier winter destinations in the Northeast. But this small town is full of delights year round: Spring brings maple sugaring season, while summer and fall are prime seasons for venturing outdoors.

Food fanatics should consider taking the 38-mile trip along Route 89 from Burlington to Stowe, where they can enjoy local foods before resting at Austrian-inspired Trapp Family Lodge.

Aerial view of Bar Harbor historic town center, with Cadillac Mountain in Acadia National Park at the background

Bar Harbor is located on Mount Desert Island, alongside Frenchman Bay.

Photo by Wangkun Jia/Shutterstock

9. Bar Harbor, Maine

Acadia National Park—one of AFAR’s Where to Go 2022 destinations—is the only national park in New England. A 30-minute drive from this nearly 50,000-acre protected area is the gateway town of Bar Harbor, Maine, which sits along Frenchman Bay. This seaside hamlet of around 5,000 people gets especially busy from May to October, when summer visitors go whale-watching and frequent the Eden Farmers’ Market.

Catch a sunrise at Agamont Park before walking along the Shore Path to enjoy views of the sun as it breaks the horizon. Sitting along the way, the Bar Harbor Inn is a luxury stay that offers a glimpse into the 1800s, when the property originally opened as the Mount Desert Reading Room.

Several houses alongside pier in the fishing village of Menemsha

In Chilmark, Massachusetts, you can find the fishing village of Menemsha.

Courtesy of Susan Pease / Alamy Stock Photo/Alamy Stock Photo

10. Chilmark, Massachusetts

Martha’s Vineyard has a reputation for its stunning coastlines and sun-kissed waters. (Don’t let Jaws fool you; shark attacks rarely happen here.) The beauty of this quintessential New England beach getaway is no secret, as its population increases more than fivefold in the summer.

While crowds flock to towns like Oak Bluffs and Edgartown, Chilmark is more of a rural take on the island. This town is home to the fishing village of Menemsha (the Menemsha Fish Market is a fine place to try lobster rolls, chowder, and other local fare) as well as the Martha’s Vineyard Film Festival every March. Fun fact: Chilmark is also the birthplace of Martha’s Vineyard Sign Language, which was introduced on the island in the early 18th century.

Colorful fall trees in rural landscape in Manchester, Vermont

Manchester is one of the best places to see Vermont’s maple trees change colors.

Photo by Steven Noroian/Shutterstock

11. Manchester, Vermont

AFAR contributor Ashlea Halpern calls Manchester, Vermont, one of the sweetest U.S. small towns to visit in the fall, in part because of its ample opportunities to see fall foliage. This town of fewer than 5,000 people is surrounded by the Taconic and Green mountains, offering beautiful nature excursions from places like the 4.6-mile Lye Brook Falls trail and the 3,848-foot Mount Equinox. Stay at the Inn at Manchester while enjoying autumnal activities; travelers can select pumpkins at Equinox Valley Nursery and pick up a handcrafted souvenir at Manchester Woodcraft.

Chloe Arrojado is the associate editor of destinations at AFAR. She’s a big fan of cafés, dancing, and asking people on the street for restaurant recommendations.
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