Why Brattleboro Is the Charming Small Town in Vermont You Need to Visit Next

Brattleboro has the allure of a quintessential Vermont town, but with fewer crowds and an emerging food and arts scene that makes it stand out among other New England destinations — not just as a place to drop your skis, but as a year-round getaway with something for everyone.

From dynamic live performances to eclectic galleries and museums, the Brattleboro community celebrates artists and makers, making it a hub for creativity and collaboration. But it’s not just about soaking in the local art; foodies and beer lovers find their own sort of paradise, too. Along with a cheese shop for every taste bud, two breweries, a distillery, and a farm-to-table eatery practically around each corner, Brattleboro is becoming a culinary hot spot.

Local annual events, like the Winter Carnival in February and the Strolling of the Heifers in June, are also known to draw visitors. The Brattleboro Area Farmers’ Market isn’t just known around town, but it draws in traffic from the entire region.

Located in southern Vermont, Brattleboro sits on the border of New Hampshire and just north of Massachusetts, with the Connecticut River flowing through town, making for an easy weekend getaway or even a day trip for much of New England and upstate New York.

Best Hotels

The Inn on Putney Road

The Inn on Putney Road is a historic, six-room bed-and-breakfast within walking distance to the shops and restaurants downtown. Two of the units are located in carriage houses next to the main building, offering a private oasis for couples or families. Guests can start the day with a two- or three-course breakfast, made with locally sourced ingredients. Explore the trails that lead from the backyard or find a quiet spot by the garden to take in the lush surroundings.

Latchis Hotel

One of two art-deco buildings still operating in the entire state of Vermont, Latchis Hotel is a historic place to rest your head, but also a hot spot for entertainment. Located in the heart of downtown, the hotel and theater has a prime location for exploring the local shops and restaurants, or taking a stroll along the river.

Setu Vermont

Known as an Indian Ayurveda school and healing center, Setu also offers weekend wellness stays. The package includes morning yoga, breakfast, evening meditation, and access to the hot tub and sauna, with the option to add programming or even personalize an individual four-day retreat.

Best Things to Do

Kipling’s Tavern

Named after local author Rudyard Kipling, Kipling’s Tavern is a cozy, historic gem of a bar that serves tasty pub food and Vermont pours. (For Kipling or Jungle Book fans, visitors can tour the Rudyard Kipling House, known as Naulakha, just outside of Brattleboro, in Dummerston).

Books and Coffee

Antidote Books and Duchess Coffee are housed in the same space, and according to Brattleboro chocolatier Dar Tavernier-Singer, it’s the perfect place “for expertly roasted and brewed coffee, espresso drinks, and a pastry.” She adds that the book side has a great selection of poetry, art, and cookbooks. Check out the events calendar to catch a signing or poetry reading from a local author.

Retreat Farm and Trails

At Retreat Farm, it’s all about food, land stewardship, and farming. Along 500 acres of conserved forest, farmland, trails, and waterways, visitors will find nine historic barns, where animals roam about, but this is so much more than a farm. The mission here is to connect people to the land and one another. Walk the 10 miles of paths and trails, sit down in the grass and listen to live music while enjoying a local beer or cheese plate, explore the labyrinth garden, check out the food trucks, or bring your own picnic.

Farmers Market

On Saturdays from May through October, Tavernier-Singer recommends visiting the farmers market. “It is the place to buy fresh veggies and locally made items, plus it has fantastic lunch options with picnic tables and live music, all on a gorgeous parcel of land on the western edge of town,” she says. One of those lunch spots is a food truck called Dosa, which comes with praise from Emily Murphy Kaur, who owns Setu, the Indian Ayurvedic healing center in town. (A dosa is South India’s version of a crepe.)

Best Shopping

Beadniks

You don’t need to be a bracelet-making Swiftie to appreciate the sheer volume of beads decorating this popular downtown shop. From glass to antique, gemstone to seed, the bead options here are endless. The store also offers gemstones, toys, books, tinctures, and other gifts.

Tavernier Chocolates

The sweet aroma from Tavernier Chocolates bellows onto Main Street, making it hard to pass up a stop at the town’s chocolate shop. While the essence of a familiar scent draws in guests, the unique chocolate combinations make you a customer for life. Cheese, pine, mushrooms, habanero peppers, tulsi, and dandelion root are among the ingredients incorporated into the bars and bonbons here. Basically, if it’s locally in season, there’s a good chance it’s in your chocolate.

Twice Upon a Time

Sprawled across three floors and 10,000 square feet, this Main Street shop is a haven for antiques, collectibles, furniture, vintage clothing, and jewelry from 100 vendors and 4,000 consignors. Kaur and husband Harmeet Singh love finding a piece of home right in town. She says, “We were pleasantly surprised to find a gem like Twice Upon a Time, where they not only knew about Ganesha (elephant-headed God), but also had a variety of Indian artifacts that we’ve collected over time.”

Best Restaurants

A Vermont Table

Tavernier-Singer and her partner, John, moved to Brattleboro 25 years ago and own Tavernier Chocolates in town. “We love A Vermont Table, including its light-filled dining room and creative plates that feature local, seasonal ingredients,” she says. While the restaurant is open for dinner during the week, it also offers an extensive brunch on Sunday.

Guilford Country Store

There’s something about a country store that helps you understand the pulse of the town. In the morning, locals stop in at Guilford Country Store to catch up over coffee and a pastry; by lunch, it’s not uncommon for table space to be scarce while folks enjoy a sandwich on fresh bread, a quick slice, or the soup of the day.

Peter Havens

An intimate setting with a bustling bistro atmosphere, Peter Havens offers an upscale, diverse menu starring classic seafood with a twist. Meanwhile, the Oyster Bar at Peter Havens serves small plates and appetizers, in addition to having a raw bar menu that rotates daily. The dim lighting here creates a romantic ambience, but it’s not unusual to see families dining here as well.

Best Time to Visit

The best time to visit Brattleboro is between June and October, when you can access the trail systems, as well as enjoy special summer events, the farmers market, and peak fall foliage as the season winds down.

How to Get There

Located in southern Vermont, on the border of New Hampshire, Brattleboro is about two hours from Boston, Albany, and Burlington, making a car the easy choice if you’re road tripping through the region. For travelers leaving their wheels behind, the Amtrak stops right in the heart of downtown. The Greyhound bus also stops in town.

How to Get Around

Brattleboro is a small, walkable town, and visitors do so not just because it’s an easy way to get around, but because there’s so much scenery to take in. Alternatively, Brattleboro Bicycle Shop and Burrows Sports offer rentals to those wanting to explore on two wheels. Ride-share options and cabs are readily available as well.