Nestled in southern Vermont along the Connecticut River, Brattleboro is a vibrant town where arts, culture, history, and nature blend seamlessly.
Known for its lively downtown, scenic trails, and thriving arts scene, Brattleboro is perfect for a weekend getaway or a longer Vermont adventure.
Here’s your ultimate guide to the best things to do in Brattleboro — from hidden gems and historic sites to outdoor adventures and local flavors.
1. Brattleboro Museum & Art Center
A hub for contemporary and regional art, this museum showcases rotating exhibits, workshops, and community programs. Perfect for art lovers or families wanting a creative afternoon.
Pro Tip: Check the calendar for seasonal exhibitions and special art events.
2. Creamery Covered Bridge
Step back in time at this charming covered bridge. Ideal for photos, leisurely walks, or a quick scenic stop while exploring the town.
3. Retreat Farm & Retreat Trails
Enjoy nature walks, birdwatching, or a peaceful hike along the Retreat Trails. The farm and trails offer a serene escape from the bustle of downtown.
Insider Tip: Early mornings are magical for spotting deer and listening to the morning bird chorus.
4. Latchis Theatre & The Stone Church
- Latchis Theatre: Historic cinema and live performances with a classic Vermont vibe.
- The Stone Church: Popular venue for concerts featuring local and national acts. Music lovers shouldn’t miss a show here.
5. Brattleboro Farmers’ Market
Open seasonally, the market features fresh produce, artisanal goods, baked treats, and handmade crafts. Perfect for tasting Vermont’s flavors and supporting local farmers.
Pro Tip: Visit in the morning for the freshest produce and to avoid the crowd.
6. Fort Dummer State Park
A scenic park with hiking trails, picnic areas, and historical significance. Ideal for families and nature lovers looking for an outdoor escape.
7. Harris Hill Ski Jump
Witness ski jumping or explore the site during off-season for a panoramic view of Brattleboro and the Connecticut River Valley.
8. Estey Organ Museum
Discover Brattleboro’s rich musical history through its historic organs. The museum features exhibits and guided tours that fascinate both music enthusiasts and history buffs.
9. Twice Upon A Time Antiques & Downtown Shops
Stroll through the town’s quaint streets to browse antiques, vintage finds, and unique boutiques. Downtown Brattleboro is full of bookstores, art galleries, and locally owned shops.
10. Saxtons River Distillery & Whetstone Beer Co.
Sample Vermont-made spirits at Saxtons River Distillery or enjoy craft beers at Whetstone Beer Co.. Both are ideal for experiencing the state’s vibrant craft beverage scene.
11. Brattleboro Bowl
Classic bowling alley fun for families or groups of friends. A relaxed way to spend an afternoon or evening in town.
12. Mount Wantastiquet Hike
Moderate hiking trails lead to spectacular views of the Connecticut River and surrounding mountains. Perfect for photography and a peaceful escape into nature.
Pro Tip: The summit is especially beautiful at sunrise or sunset.
13. Scott Farm Orchard
Visit this working orchard for apple picking, cider tasting, and seasonal events. A must-do in the fall for families or anyone looking to enjoy Vermont traditions.
14. New England Center for Circus Arts (NECCA)
Learn trapeze, acrobatics, and other circus arts or watch talented students perform. NECCA brings a playful, artistic energy to Brattleboro.
15. Vermont Jazz Center
Live jazz performances and music education programs make this a cultural hotspot. Don’t miss their seasonal concerts or special workshops.
16. Bratt First Friday & Gallery Walk
Every first Friday, the town comes alive with gallery openings, live music, and art events. A perfect way to explore Brattleboro’s creative community.
17. Brattleboro Country Club & Living Memorial Park
- Brattleboro Country Club: Golf enthusiasts can enjoy a scenic course with rolling Vermont landscapes.
- Living Memorial Park: Walking trails, monuments, and green spaces make it perfect for a relaxing afternoon.
18. Brattleboro Words Trail
A unique literary trail featuring poetry and quotes scattered along a scenic path. Combines culture and nature for a thoughtful outdoor experience.
19. Madame Sherri Forest (Chesterfield, NH)
Just across the border, explore the ruins of Madame Sherri’s castle amidst forested hiking trails. Ideal for adventurers and history buffs.
20. Epsilon Spires & River Gallery School of Art
- Epsilon Spires: Fascinating rock formations and nature walks.
- River Gallery School of Art: Offers workshops, exhibitions, and hands-on experiences for artists of all levels.
Final Thoughts
Brattleboro is more than a small town — it’s a lively Vermont escape blending arts, culture, nature, and local flavors.
From hikes and scenic bridges to galleries, breweries, and seasonal events, there’s something for everyone.
Share this content: