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Tucked along the banks of the Connecticut and West Rivers in southeastern Vermont, Brattleboro is one of New England's most vibrant small towns. With a population of just over 12,000, it punches well above its weight — routinely named one of the top small art towns in the country, and beloved for its independent spirit, thriving food scene, and genuinely walkable downtown. It makes for an ideal half-day or full-day excursion from Otherland Hotel.

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BRATTLEBORO FIRST FRIDAYS & ART WALK

Brattleboro First Fridays are Ultra-Festive Block Parties on Elliot Street & Harmony Lot. Vehicles are kicked out for the night and instead you can find all sorts of people-y fun.

The MAKER’S MARKET at First Fridays: Elliot Street is transformed into an artisan market featuring 30+ rotating makers, upcyclers, and artists. New this year, DBA is supporting Local Booth Grants allowing greater accessibility for artists to participate.

LIVE MUSIC at First Fridays: Every month Harmony Lot becomes Brattleboro’s FREE outdoor concert hall. For May, we welcome Juice and Emily Margaret Band to the stage. Juice is a five piece NYC act- tight grooves, radiant harmonies, jaw- dropping solos. Big stage energy packs an unforgettable punch. The Emily Margaret Band has won Brattleboro’s hearts with their unforgettable R&B inspired sound.

FOOD TRUCK FOOD COURT: We welcome 10-15 food trucks to Harmony Lot each month. You can grab something quick there, OR make a reservation at one of our outrageously good downtown restaurants.

Lawson’s Finest Presents: The First Friday OUTDOOR BEER GARDEN. Stone Church does the slinging and Vermont’s own Lawson’s Finest offers up ice cold beverages in all of Harmony Lot. Cheers!

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ARTS & CULTURE

Brattleboro's arts scene is the heart of the town. The Brattleboro Museum & Art Center, housed in a beautifully restored 1915 Union Station building, shows rotating exhibitions by regional and international artists. Gallery in the Woods is a must-visit, featuring work from over 200 artists worldwide alongside a rotating cast of locally made ceramics, jewelry, and sculpture. On the first Friday of every month, the town comes alive for Gallery Walk — an open-house evening where galleries, shops, and studios throw open their doors, with food trucks and live music in the streets.

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FOOD & DRINK

Brattleboro's dining scene is far more eclectic than you might expect from a small Vermont town. From farm-to-table restaurants and independent coffee shops to ethnic eateries and beloved local favorites, there is something for every appetite. The Brattleboro Area Farmers Market is a wonderful stop on a Saturday morning, brimming with local produce, baked goods, and artisan goods. Downtown is compact and walkable, making it easy to graze your way through the day.

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LIVE MUSIC & EVENTS

Music runs deep in Brattleboro. The Stone Church — a beautifully converted 19th-century church — hosts an impressive roster of internationally touring acts alongside emerging local artists. Nearby, Epsilon Spires (another repurposed church) offers a calendar of art, film, and experimental music. The Vermont Jazz Center rounds out the town's well-earned reputation as one of New England's leading jazz destinations.

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OUTDOORS

If the outdoors calls, Brattleboro delivers there too. Retreat Farm — a short walk from downtown — offers trails, farm animals, and open meadows along the river. The Connecticut River is a draw for kayakers and canoeists, and the trails up Mount Wantastiquet in neighbouring New Hampshire offer sweeping views of the town and valley below. The historic Creamery Covered Bridge in West Brattleboro is a classic Vermont photo stop.

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GOOD TO KNOW

Distance from Otherland: Approximately 15 minutes by car, heading south on Route 30

Best time to visit: Year-round — each season brings its own character, from summer farmers markets to winter carnivals

Don't miss: Gallery Walk (first Friday of the month), Retreat Farm trails, and the Brattleboro Museum & Art Center

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