BRATTLEBORO
Brattleboro sits on Vermont's southeastern border at the confluence of the West River and the Connecticut River, anchoring southern Vermont's creative economy with a walkable, three-block downtown of independent shops, bookstores, and cafes.
You can catch touring acts inside a renovated 147-year-old Victorian Gothic church at The Stone Church on Main Street, or head to Epsilon Spires, another converted church just down the block hosting music and film. The Vermont Jazz Center holds court at Cotton Mill Hill, a repurposed industrial complex that now houses dozens of studios and creative enterprises. The 1938 Art Deco Latchis Theatre programs first-run films and live performances, while the Hooker-Dunham Theater adds gallery shows and intimate stage events to the mix.
A compact, semi-urban downtown where organ-factory history meets monthly Gallery Walk openings and two independent record shops. The Brattleboro Food Co-op and first-Friday art crawls anchor a town that runs on cooperative economics and creative enterprise.
Tip: First Fridays from May through October bring the Gallery Walk, when storefronts and studios across downtown open for exhibitions and live music — a good night to check multiple venues on foot.
Neighborhoods: Downtown • West Brattleboro • Cotton Mill Hill
WEEK OF FEBRUARY 23, 2026
MONDAY - 2/23
- Windham Philharmonic: The Magic Flute at 7:00pm opera vibes
WEDNESDAY - 2/25
- Revenant Sea let's vibe
FRIDAY - 2/27
- Utsav Lal get lost
FRIDAY - 4/10
- Jeff Rapsis organ vibes
- 2025-2026 Solo Jazz Piano Festival at 7:30pm piano fest
SATURDAY - 4/11
- 2025-2026 Solo Jazz Piano Festival at 10:00pm piano fest
FRIDAY - 4/17
- Olivia Block - Lea Bertucci soundscape
SATURDAY - 4/18
- A Moondog Tribute: Trimbtych let's jam