Brattleboro has a thriving arts community. The town is listed in John Villani's book The 100 Best Small Art Towns in America, in which it ranks number nine among towns with a population of 30,000 or under.
On the first Friday of every month, an event known as the Gallery Walk is held, in which galleries, artists, and arts organizations open their doors to the public to display new work or hold performances. Included in the organizations that participate are the Brattleboro Museum and Art Center, the Hooker-Dunham Theater and Gallery, the In-Sight Photography Project, River Gallery School, Through the Music, and the Windham Art Gallery.
Other notable arts organizations in Brattleboro include the Brattleboro Music Center, the Vermont Theatre Company, the New England Youth Theater, the Brattleboro Women's Chorus, the New England Center for Circus Arts (NECCA) the Vermont Performance Lab and the Vermont Jazz Center.
Annual events in Brattleboro include:
* The Winter Carnival in February.
* Harris Hill ski-jumping competition in February.
* Women's Film Festival in March.
* Maple Open House Weekend in March.
* River Gallery School benefit auction in March.
* Taste of the Town in May.
* Slow Living Summit, late May or early June, just prior to Strolling of the Heifers weekend
* Strolling of the Heifers the first full weekend in June.
* Vermont Theatre Company's Shakespeare-in-the-Park in June and July.
* Brattleboro Free Folk Festival, begun in 2003.
* Brattleboro Literary Festival in September