Small-town life is on full display in New England. Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont are known for their collegiate vibes, rugged beaches and mountains, beautiful foliage, and a long and rich history. Indigenous tribes such as the Abenaki and the Wampanoag, among others, have lived in the region for 30,000 years. Some of the country’s oldest extant buildings and streets are found here, dating back to the 1600s. For history buffs, hikers, foliage enthusiasts, or anyone who wants to eat just-caught seafood, here are 11 ultra-charming towns to visit in New England.
Woodstock, Vermont
Woodstock, Vermont, is a historian’s dream. Many buildings in this town, founded 15 years before the U.S., are on the National Register of Historic Places. These include 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 the historic buildings of the Marsh-Billings-Rockefeller National Historical Park are another way to explore the small town’s natural landscape and sites such as the Belvedere Complex.
Where to stay
- Book now: Woodstock Inn & Resort
Reserve a room at the upscale Woodstock Inn & Resort in Woodstock’s downtown, built in 1892 for $120,000 ($4.3 million today). Its 142 guest rooms have gingham curtains, framed botanical prints, and seafoam-green bedspreads atop sturdy wooden beds. The hotel has a ski area, a golf course, tennis courts, and a pool. The hotel’s five restaurants are supplied by its own Kelly Way Gardens, which grows more than 200 varieties of vegetables and 75 varieties of berries and orchard fruits.
Williamstown is also home to the Williamstown Theatre Festival, one of the biggest theater festivals in the country.
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Williamstown, Massachusetts
Williamstown, Massachusetts, has been a well-known stop for road-trippers passing through the 63-mile Mohawk Trail. The town is home to Williams College, which has an art museum on campus and events like the ultra-popular Williamstown Theatre Festival each summer, not to mention that the Clark Museum is nearby. It’s in autumn that the town really shines, with full-on collegiate vibes and beautiful fall foliage starting in mid-September. North Adams, a 10-minute drive down the road, even hosts a fall festival on the first Sunday of October that celebrates the changing leaves. Try the 11.2-mile Ashuwillticook Rail Trail and Mount Greylock for the best views of the tree colors.
Where to Stay
- Book now: The Williams Inn
The Williams Inn has 64 rooms with pistachio-green accent walls, antique-inspired wooden furniture—including Shaker-style desk chairs—and sliding barn doors in soft gray. Borrow one of the complimentary bikes to tool around town.
Ogunquit isn’t just a summer spot.
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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, head to lobster spots like Barnacle Billy’s, Lobster Pound, and the Oarweed (following a fire, it reopens in April 2026)—all of which stay open until early November. And the festivities don’t end when winter rolls around. The annual Christmas by the Sea celebration is a great time to explore Ogunquit’s small-town charm, whether through a gallery tour, a choral concert, or an arts-and-crafts showcase.
Where to stay
- Book now: Nellie Littlefield Inn & Spa
This handsome three-story Victorian, a block from the sea, has eight rooms. Each is different, but all have antique-leaning furniture and decor, including a Dodger-blue wooden four-poster bed or a clawfoot cast-iron tub. Lovely amenities include an outdoor saltwater hot tub and pool, beach gear to borrow, and a breakfast spread every morning and baked goods every afternoon.
Conway is near the Saco River on the border of New Hampshire and Maine.
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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. Travelers can see the area’s nature by train, too: Board the Conway Scenic Railroad Mountaineer to admire the Crawford Notch pass.
If you’re up for a serious challenge, drive an hour north and hike the 18-mile Presidential Traverse Trail; be prepared to scramble up some rocks on this hike.
Where to stay
The wraparound porch at The Kearsarge Inn, a late-19th-century New England colonial-style home, practically begs guests to sip a cup of tea in one of the wicker chairs. This is a homey, old-school inn where you can really lean into antique New England vibes—think sleigh beds, patchwork quilts, and gas fireplaces. At the opposite end of the spectrum is Villa Hygge, which has 11 suites designed to look like Scandinavian cabins (wood cladding, white linens and furniture, tons of sheepskin-style throws). The hotel is popular for its spa, which includes a sauna, a salt lounge, and several treatment options.
Related: Fall Foliage Is Better by Rail on These 13 Scenic Train Trips
Provincetown has long been a haven for LGBTQ+ beach-goers.
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Provincetown, Massachusetts
This town on the northern tip of Cape Cod has been a longtime haven for artists (it’s America’s oldest continuous art colony), evident in events like the Friday night Gallery Strolls and in spaces like Provincetown Art Association and Museum. The town is also popular among those in the LGBTQ+ community. LGBTQ+ events hosted throughout the year include Pride in early June and the weeklong TransWeek in October (previously known as Fantasia Fair), the longest-running transgender conference in the world.
Where to stay
- Book now: Awol
Each of the bright, beachy-modern rooms has an outdoor space (a patio for those on the ground floor and a balcony for second-floor guests), where you can relax with a beach read. Convivial common spaces include the heated outdoor pool and the firepit and the picnic tables overlooking the moors. Stroll into town for dinner or borrow one of the hotel’s Retrospec bicycles and pedal along the coast.
Westerly, located in Washington County, was first settled in the 17th century.
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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 ideal for languid mornings by the shore, after which you can meander through Westerly’s vibrant downtown dotted with boutiques.
Where to stay
- Book now: Ocean House Hotel
For a place to rest your head, arguably no stay beats the luxury of the Ocean House Hotel, a sprawling Victorian property that sits on Watch Hill. The 46 rooms and 23 suites have marble baths, dark wooden four-poster beds dressed in 400-thread-count linens and, in some rooms, partial or full ocean views. Play croquet or shuffleboard on the property, head down to the beach and laze under one of the hotel’s cabanas, or borrow a bicycle to cruise into town.
Mystic’s history with shipbuilding goes back more than two centuries.
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Mystic, Connecticut
Julia Roberts and co. made Mystic, Connecticut, famous with the 1988 romantic comedy movie Mystic Pizza (where you can still go for a pie). The movie portrays a seaport destination characterized by slow living, and 37 years later, this idyllic spirit remains intact in this town of 4,400.
Take in Mystic’s nautical roots at the Mystic Seaport Museum, which has exhibits on maritime history, including one of figureheads and ship carvings. You can imagine life alongside wood-carvers and riggers during the 1800s by visiting the museum’s re-created 19th-century Seaport Village. If you’re visiting Mystic in summer, tuck into a lobster roll at a wooden picnic table overlooking the Mystic River at Sea View Snack Bar. Year-round, stylish Oyster Club serves its namesake bivalves alongside other local seafood (clams, monkfish, tuna crudo). The brand-new spot to check out, though, is Mystic Fish Camp, from
David Standridge, named the best chef in the Northeast at the 2024 James Beard Awards. Standridge used to work in New York City restaurants, then relocated to Mystic to open The Shipwright’s Daughter in 2020. As in that restaurant, his new spot is focused on sustainable, local fish, but in a more casual setting.
Where to stay
- Book now: Captain’s Mansion
The Captain’s Mansion is just that: a stately home built in 1853 by a sea captain (today it sits a convenient two blocks from Mystic Pizza). The eight rooms have antique-style, heavy wooden furniture, period bathrooms, and pretty floral curtains. Within the expansive house, guests can read in comfortable armchairs and sofas or sit in a rocking chair on the redbrick patio.
Stowe is a ski haven in the winter, but don’t miss it in the summer for hiking or for maple sugaring in the fall.
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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.
Ten minutes from Stowe is Smugglers’ Notch State Park, named for the narrow pass in the Green Mountains through which Vermonters used to smuggle goods from Canada in the 1800s. It’s an ideal place for a hike, especially during autumn, when its thickets of trees turn into a showcase of red, gold, and orange.
Where to stay
- Book now: Field Guide Lodge
For a cozy, escape-to-the-woods atmosphere, head to the 30-room Field Guide Lodge. It’s embellished with aspen tree wallpaper, deer motifs, and red-and-black plaid armchairs that look like your favorite flannel shirt. If you don’t want to be indoors, warm up in the hot tub, or swap foliage tips with other guests over a pint of Vermont craft beer around the firepit.
Bar Harbor is located on Mount Desert Island, alongside Frenchman Bay.
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Bar Harbor, Maine
A 30-minute drive from Acadia National Park—the only national park in New England—is the gateway town of Bar Harbor, which sits along Frenchman Bay. This seaside hamlet of about 5,000 people is packed from May to October, when summer visitors go whale-watching, frequent the Eden Farmers’ Market, and pop in and out of the quaint boutiques that fill the town’s streets. Catch a sunrise at Agamont Park before walking along the Shore Path to enjoy views of the sun as it breaks the horizon. Then pop over to bakery-café The Stadium, Bar Harbor, known for its cider doughnuts and popovers. Starting in September, all those trees in Acadia turn colors, and the scenery gets even better. Keep an eye on Maine’s official foliage tracker to plan a visit during peak leaf-peeping season.
Where to stay
- Book now: Bar Harbor Inn
Bar Harbor Inn is a luxury stay in an 1887 former private club, the Mount Desert Reading Room. The 153 spacious rooms have views of the ocean, the bay, or the hotel’s garden and manicured grounds, and some have balconies. The Atlantic is rather frigid for a swim, but guests here can enjoy the heated outdoor pool and hot tub, followed by the daily afternoon cookies-and-coffee setup.
In Chilmark, Massachusetts, you can find the fishing village of Menemsha.
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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 nearly tenfold 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 great place to try lobster rolls, chowder, and other local fare), as well as the Martha’s Vineyard Film Festival every March. But be sure to get off the beaten track, too, and learn about a unique history here: Chilmark was the birthplace of Martha’s Vineyard Sign Language (MVSL), when the town was a haven for deaf people in the 1800s. The Martha’s Vineyard Chamber of Commerce has a driving tour map of key historical sites, including the Chilmark library, which was the former home of the person believed to be the last fluent signer of MVSL.
Where to stay
Chillmark’s lack of tourists compared to other Martha’s Vineyard towns is central to its appeal, but that also means there are fewer places to stay. Your best bet is to rent a house, and do so early. Hillside Oak, a bright four-bedroom, four-bathroom house, and the Eliot Noyes, a four-bedroom midcentury stunner with a pool, can both be booked through Marriott Bonvoy.
Related: Martha’s Vineyard Was Once a Haven for the Deaf. I Took a Trip to Find Out If It Still Is.
Manchester is one of the best places to see Vermont’s maple trees change colors.
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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, such as the moderate 4.6-mile Lye Brook Falls trail and Mount Equinox. In town, travelers can select pumpkins at Equinox Valley Nursery and pick up a handcrafted souvenir at Manchester Woodcraft. A sandwich from Zoey’s Deli, like the Turkey Royale with cranberry mayo, packs well for a hike.
Where to stay
Book now: Inn at Manchester; Kimpton Taconic Hotel
The 21-room, family-run Inn at Manchester is a picture-perfect B&B on four peaceful, grassy acres. Take in views of the nearby forests from your room or from the light-filled dining room. Fuel up for a day of leaf-peeping with the inn’s cottage cakes, its spin on pancakes served with warm apricot preserves. Down the road is the 88-room Kimpton Taconic Hotel, in a clapboard-style building modeled after those found across New England. Grab one of the black wooden rocking chairs on the long front porch and dig into a good book.
This article was originally published in 2023 and most recently updated on September 4, 2025, with current information.
