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The first Friday of each month from 5:30PM-8:30PM. Shops and galleries are open and people come to see the sights. A good way to get a feel for the locals. See the fashion show at Twice Upon a Time, a local consignment shop.
Small museum with consistently changing exhibits since they have no collection. Current admission ranges from $4 for students to $8 for adults. Free for kids under 6.
A very cool old theater that hosts new films, old films, live theater, and guest speakers. On Halloween they show the Rocky Horror Picture Show, which is great fun. They also show films during the Brattleboro Women's Film Festival.