GALLERY WALK, Brattleboro, Vermont - A Monthly First-Friday Celebration! Gallery Walk in Brattleboro, Vermont happens on the first Friday of each Month from 5:30 to 8:30 PM. See the work of leading New England artists in a welcoming setting: paintings, drawings, sculpture, prints and photography. If you are staying in Vermont, downtown Brattleboro is the perfect blend of country charm and city convenience.