Brattleboro was Vermont’s first town. Colonists pushing north on the Connecticut River from more puritanical parts of New England must have recognized its potential as a progressive enclave. Over the years, the settlement has welcomed migrants of every stripe, including back-to-the-landers who established communes in open-minded Windham County. The hippies are still there, as evidenced by Brattleboro’s abundance of used counterculture bookstores and funky clothing and jewelry shops. The town remains Ground Zero for renewable-energy activism and antinuclear protest, most of it directed at Vermont Yankee, its neighbor to the south.
In keeping with its progressive bent, Brattleboro is home to a historic mental hospital — one of the first 10 psychiatric hospitals in the United States. In 1834, Anna Marsh donated $10,000 to found the Brattleboro Retreat , which remains one of the town’s premier and most visible institutions. The new facility was patterned on a Quaker concept called “moral treatment,” a radical concept at the time, that argued for treating patients with dignity and respect in a family-like setting. The Brattleboro Retreat pioneered numerous innovations to benefit its patients, including a newspaper, a gymnasium, camping programs, swimming pools and the first self-sufficient dairy farm on the grounds of a mental hospital.
Brattleboro was “localvore” before there was a word for it. For years, the place to eat was Common Ground, the legendary worker-owned restaurant where diners served themselves, ate whole grains, and bussed their own dishes. Although that restaurant is now closed, the food in town is still good, albeit pricier. Among the finest places to eat in Brattleboro are Peter Havens  and T.J. Buckley’s. The latter seats a maximum of 18 in a converted 1920s diner.
No reservation is required for Brattleboro’s Strolling of the Heifers Weekend  in early June. A peaceful alternative to Pamplona’s “Running of the Bulls,” it’s an annual celebration of local agriculture — and the national press loves it. The three-day event opens with a parade, led by kids and cows, followed by a Green Expo and Dairy Festival. It also includes B-boro’s first-Friday Gallery Walk, a monthly tradition.
Art is always part of the equation in Brattleboro — perhaps because it was home to the Estey Organ Company for more than a century. Founded in 1846, the company manufactured organs large and small and sold them all over the world. These included some 520,000 reed organs, 3200 pipe organs and, toward the end of its lifetime, a foray into the electronic realm. A local group recently opened the Estey Organ Museum, the mission of which is to collect, preserve and interpret the physical and cultural heritage of the company. For now, the museum’s Engine House Galley is open 1 to 4 p.m. on Saturdays, June through October. Guided tours are available.
Brattleboro’s cultural life didn’t stop when the organ music did — it’s one of the 100 Best Art Towns in America, according to author John Villani. The Art Deco Latchis Theater  shows first-run, art and independent films. The New England Youth Theater  offers classes for young people in all aspects of theater, from acting to backstage technical skills. Their summer program performances almost always sell out. On the same “campus” is the one-of-a-kind New England Center for Circus Arts , with circus-training classes for thrill seekers of all ages.
Brattleboro’s artistic wealth extends to the surrounding countryside — at least in the summer — earning Windham County international renown for its music festivals. Since 1961, the Marlboro Music Festival  has been drawing professional chamber musicians to a “retreat” that takes place on the campus of Marlboro College. They give public concerts on weekends. A little further north in Putney, the 40-year-old Yellow Barn Music School and Festival  is a professional training program for chamber musicians. Public concerts take place from mid-June through early August.