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Brattleboro was chartered in 1753 by New Hampshire Governor Benning Wentworth and named after William Brattle, a loyalist minister. The town grew rapidly during the 19th century as a center for paper manufacturing and publishing, powered by the Whetstone Brook. The arrival of the railroad in 1849 transformed Brattleboro into a regional transportation hub connecting Vermont to Boston and Montreal. Throughout the Civil War era, the town was an important stop on the Underground Railroad. Brattleboro later became known as a retreat for artists and writers, including Rudyard Kipling who lived nearby. Today it preserves its historic downtown with well-maintained 19th-century commercial architecture.
Downtown Brattleboro offers a walkable Main Street filled with independent bookstores, art galleries, and specialty shops. The Brattleboro Museum and Art Center presents contemporary exhibitions in a restored railroad station along the Connecticut River. Visitors can browse the Brattleboro Food Co-op, a community-owned market offering local produce and Vermont specialty foods. The Latchis Theatre, a 1938 Art Deco cinema and performance venue, screens films and hosts live music. On weekends the Brattleboro Winter Farmers Market draws crowds to its indoor venue from November through March. Kayaking on the Connecticut River and cycling the nearby scenic backroads are favored warm-weather activities.
The Creamery Covered Bridge on Guilford Street is a classic Vermont landmark built in 1879 with a distinctive lattice truss design. The Retreat Tower, a stone observation tower constructed in 1887, offers panoramic views of the Connecticut River Valley and Mount Wantastiquet. Nearby Naulahka, Rudyard Kipling’s former estate, is where he wrote The Jungle Book and Captains Courageous. The Brattleboro Common hosts summer band concerts and serves as the town’s central gathering space. Historic Arch Street features some of the oldest surviving houses in town, dating to the early 1800s.
The West River Trail follows an old railroad corridor along the river, providing level walking and cycling for all ages. Fort Dummer State Park offers hiking trails, picnic areas, and campsites on the site of Vermont’s oldest English settlement. The Wantastiquet Mountain Trail across the river in New Hampshire rewards hikers with sweeping views back toward Brattleboro and the Green Mountains. Living Memorial Park maintains a community ski hill with a rope tow, along with a swimming pool and walking paths. Canoeing and paddleboarding on the Connecticut River give paddlers a peaceful perspective of the town.
The Brattleboro Museum and Art Center is housed in a beautifully restored 1915 Union Station and features rotating exhibits of modern and contemporary art. The Latchis Hotel and Theatre, a rare surviving Art Deco complex, is a National Register landmark with original murals and terrazzo floors. Nearby Grafton Village Cheese Company produces award-winning cheddar and offers tastings at its retail shop. The Tasha Tudor Museum celebrates the life and work of the beloved children’s book illustrator who made her home in nearby Marlboro. The Brattleboro Retreat, founded in 1834, pioneered humane mental health treatment and its historic campus is listed on the National Register of Historic Places.
Autumn brings spectacular foliage throughout the Connecticut River Valley, with peak colors typically arriving in early October when the hillsides blaze with orange, red, and gold. Summer offers warm days ideal for paddling, cycling, and attending the Brattleboro Literary Festival and the Strolling of the Heifers parade. Winter transforms the landscape into a quiet New England scene with cross-country skiing at Living Memorial Park and easy access to nearby downhill resorts. Spring arrives slowly in Vermont, but by May the wildflowers bloom along the West River Trail and farmers markets return outdoors. The Gallery Walk on the first Friday of each month makes any season a good time to explore the thriving local arts scene.
Here are some of our favorite things to do near Brattleboro. Take your pick!
The Creamery Covered Bridge was built in 1879 spanning Whetstone Brook on Guilford Street in Brattleboro, Vermont. Constructed using the Town lattice truss design , the bridge measures 80 feet in length and has stood for well over a century as one o…
Fort Dummer State Park covers 217 acres of forested land in the Connecticut River Valley, just outside Brattleboro, Vermont . The park is named for Fort Dummer , built in 1724 as Vermont’s first permanent European settlement, where forty-three Engli…