6 Charming New England Towns Perfect for a Weekend Getaway
From coastal villages to inland hideaways, these under-the-radar towns offer the perfect mix of history, nature, and seriously good food
As a born-and-raised New Englander, I’m always eager to steer visitors beyond the usual stops. From summer seafood pulled straight from the water to snow-dusted winter trails and golden mountains in the fall, this region is worth visiting in every season. After a lifetime of exploring, these six destinations stand out as some of the best small towns in New England—offering experiences that go beyond the crowds and typical tourist activities.
Woodstock, Vermont
This quintessential Vermont town is known for its stunning fall leaf-peeping, but it’s just as lovely year-round. In summer, farmers’ markets burst with long-awaited produce, cycling routes abound, and visitors can cool off with a dip in the Ottauquechee River that runs through town. Billings Farm & Museum is a family-friendly stop where you can meet the working dairy cows and get a behind-the-scenes look at a Vermont cheese operation.
To embrace full-on New England charm, book a room at The Woodstock Inn & Resort, a AAA Four Diamond hotel home to some of the best restaurants in town. Be sure you don’t leave the state without trying a maple creemee (Vermont’s signature maple-flavored soft-serve ice cream) from Woodstock Scoops—yes, even during ski season.
For downhill skiers, Killington Mountain is just a 20-minute drive from Woodstock’s center. The town also offers miles of beautiful cross-country trails to explore in every season.
Amherst, Massachusetts
If you’re looking for idyll with a side of culture and academia, head to Amherst, home to Amherst College, the University of Massachusetts, and Hampshire College. Whether school is in session or not, the restaurant-filled downtown is always bustling with activity, from weekend farmers’ markets to seasonal carnivals.
The cozy Inn on Boltwood is within walking distance of both college campuses and the Emily Dickinson House Museum, a must-visit for literature lovers. The surrounding Pioneer Valley also offers excellent yet approachable hiking. Start by summiting The Notch on the Holyoke Range, or opt for a flat cycle along the miles-long Norwottuck Rail Trail.
Science lovers will enjoy the Beneski Natural History Museum, while little ones (and their adults) will be drawn to The Eric Carle Museum of Picture Book Art, a museum dedicated to the creator of the beloved children’s book The Very Hungry Caterpillar.
Atkins Farms Country Market is well-known for its excellent apple cider donuts, available year-round. And for a memorable dinner, head to nearby Sunderland to The Blue Heron, where globally inspired and locally sourced dishes are served in the original Old Town Hall.
Camden, Maine
Situated perfectly between the coast and the mountains, Camden is worth the drive year-round. Its walkable downtown, known as the High Street Historic District, is ideal for shoppers and window browsers in search of local crafts, specialty goods, and boutique art galleries.
Grab a classic Maine lobster roll overlooking the water at Salt Wharf, or enjoy a casual bite at beloved local clam shack Scott’s Place. For breakfast, try one of everything from French-style bakery The Place, where flaky pastries and strong coffee fuel slow mornings before a day on the harbor or the trails.
Camden Snow Bowl is the only New England ski area where you can see the ocean from the chairlift, and for non-skiers, the tubing is first-rate.
For lodging, consider one of these AAA Four Diamond properties: Camden Harbor Inn is a lovely boutique property offering a luxurious stay, while 16 Bay View sits in the heart of downtown and provides a more casual boutique option.
Essex, Connecticut
The riverside town of Essex is a destination for history lovers. A 19th-century shipbuilding hub, it has maintained its maritime charm, with Victorian and Cape Cod-style architecture lining its scenic streets.
Stay or dine at The Griswold Inn, one of the oldest continuously operating inns in the US, at nearly 250 years old. It feels especially cozy and festive during the winter holiday season. If you’re visiting in spring, the annual Burning of the Ships Parade each May commemorates a British raid on the town during the War of 1812, honoring a pivotal moment in Essex’s history and the community’s resilience.
The Essex Steam Train & Riverboat Museum offers narrated tours by riverboat and vintage steam locomotive through the Connecticut River Valley. It’s a scenic way to explore the landscape and waterway that shaped the region.
To round out the rest of your time, browse the town’s galleries, shops, and waterfront restaurants, and don’t miss picking up a famous chocolate chip cookie from Chocolate Geeks—a local favorite.
Hanover, New Hampshire
Hanover marries the pomp and circumstance of Ivy League rigor with the relaxed patina of a New England small town. Nestled on the border of Vermont, there’s something to do here year-round, starting with a stroll around the picture-perfect Dartmouth College campus. The Hood Museum of Art features an impressive collection—and admission is free. Also, be sure to check the performance calendar at Dartmouth’s Hopkins Center for the Arts (locally known as “The Hop”), which hosts rotating dance, theater, and musical productions.
In the warmer months, rent a kayak or canoe to paddle along the Connecticut River, or explore the extensive network of trails that surround the town. Winter is for snowshoeing, cross-country, and downhill skiing—and the Dartmouth Skiway is a welcoming hill for beginners and families.
The AAA Four Diamond Hanover Inn Dartmouth is centrally located and offers comfortable, cozy rooms. For dinner, try upscale New American cuisine at PINE Restaurant, or go college-town casual at Molly’s Restaurant & Bar, where you can mingle with locals and college students over burgers and craft beer.
Jamestown, Rhode Island
Rhode Island is a tiny state packed with visit-worthy beachside towns. Jamestown has all the coastal character of its buzzier neighbor Newport, just across the bridge, but without the crowds. While it’s busiest during the summer, Jamestown is worth a visit in the off-season to enjoy scenic hiking trails and fishing in Fort Wetherill State Park and cliffside Beavertail State Park, home to the Beavertail Lighthouse Museum—one of the oldest lighthouses in the country.
The island town is full of homey boutique vacation rentals and guesthouses. For a more luxurious experience, stay across the water in Newport at Forty 1° North or The Vanderbilt, both AAA Four Diamond properties.
Jamestown’s small but bustling downtown is a bit of a food destination. Try Crudo for excellent oysters and Italian fare; Our Table Jamestown for fresh seafood in a casual environment; or 1 Ferry Wharf for classic New England seafood paired with oceanfront views. Slice of Heaven, where hearty, homemade breakfast and lunch dishes are served, is a must-visit for morning or midday meals.
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In every season, these small New England towns offer a peek at the region’s picturesque beauty and rich culture for not only visitors from afar but also locals like me.