Gallery Walk
(http://www.gallerywalk.org/). 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.
Hooker-Dunham Theater & Gallery
The Hooker-Dunham Theater puts on concerts and dramatic performances. Tickets are usually very reasonably priced. The gallery has an ever-changing selection of art.
Latchis Hotel & Theater
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.
Brattleboro Farmer's Market
The Brattleboro Area Farmers' Market is Southern Vermont's premier farmers' market featuring over 50 vendors with agricultural products, crafts, live music and animals and ethnic foods from around the world. Whether you are local or a tourist, you can stop by to get your weekly produce and grab a quick lunch, or come with your family and stay for the day! In the winter the market is held in the River Garden on Main Street in downtown Brattleboro.