10 Awesome Things To Do Near West Brattleboro, Vermont
If you’re dreaming about a small New England getaway,
West Brattleboro, Vermont is a great place to start. Tucked into
Windham County, it has that laid-back Vermont vibe, rolling hills, and easy access to trails, farms, and cool artsy spots.
Whether you’re planning a weekend trip from Boston or New York, or just passing through southern Vermont, here are
10 fun things to do near West Brattleboro that show off the best of the area.
1. Wander Downtown Brattleboro’s Artsy Main Street
Just a few minutes from West Brattleboro,
Downtown Brattleboro has a funky, creative feel you don’t always find in a small town.
Stroll along Main Street and you’ll find:
- Independent bookstores and music shops
- Local art galleries and studios
- Cafés with good coffee and fresh pastries
- Vintage and thrift stores
Pop into places like the local co-op for Vermont cheese, maple products, and fresh-baked bread. If you like people-watching, grab a seat by a window and soak in the mix of artists, students, and travelers.
It’s an easy half-day activity, and you can walk the whole downtown area in comfortable shoes. Parking is usually pretty straightforward with metered spots and lots nearby.
2. Hike (or Drive) Up to Wantastiquet Mountain for Big Views
Want a great view without needing hardcore hiking skills? Head to
Mount Wantastiquet, just across the Connecticut River from Brattleboro in New Hampshire. It’s only a short drive from West Brattleboro.
The main trail is about 3 miles round-trip, and while parts are steep, it’s very doable for most people who are reasonably active. At the top, you’re rewarded with sweeping views of:
- Brattleboro and West Brattleboro
- The Connecticut River
- Rolling Vermont and New Hampshire hills
Bring water, sturdy shoes, and maybe a light snack. On clear days, this is one of the
best free things to do near West Brattleboro.
3. Explore the West River Trail
If you like being outdoors but don’t want a tough hike, the
West River Trail is a peaceful choice. Parts of the trail are relatively flat and follow the river, making it great for:
- Walking
- Running
- Casual biking
- Family strolls with kids
You’ll find river views, forested sections, and the kind of quiet that lets you actually hear the water and the wind in the trees. In the fall, the foliage along the trail can be incredible, with bright reds, oranges, and golds.
If you’ve ever wished you could hit “pause” on life for an hour, this is a good spot to do it.
4. Visit Local Farms and Farm Stands
West Brattleboro sits in classic Vermont farm country. That means you’re never far from a farm stand full of seasonal produce, maple syrup, and sometimes fresh flowers.
Depending on the time of year, you might find:
- Local apples, berries, and peaches
- Maple syrup and maple candy
- Fresh eggs and cheeses
- Cider donuts in the fall
Many small farms around West Brattleboro and wider Windham County set up seasonal farm stands right by the road. If you see a little sign for “Maple” or “Farm Fresh Eggs,” it’s often worth pulling over.
Buying directly from local farmers is not just tasty; it also supports the local Vermont economy. Plus, it’s fun to bring home real Vermont maple syrup as a souvenir.
5. Check Out the Brattleboro Farmers’ Market
If you’re visiting in the warmer months (usually May through October), the
Brattleboro Farmers’ Market is a must-do.
Here’s what you can expect:
- Fresh fruits and veggies from local farms
- Handmade crafts and jewelry
- Prepared foods from around the world
- Live music on many weekends
It’s family-friendly, colorful, and very “Vermont.” You can grab lunch, chat with local farmers and makers, and pick up unique gifts. It’s also a great place to people-watch and get a feel for the community.
Tip: Arrive earlier in the day for easier parking and the best selection.
6. Tour the Brattleboro Museum & Art Center
If you love art, or even if you’re just “art-curious,” the
Brattleboro Museum & Art Center downtown is worth a visit.
The museum focuses on contemporary art and rotating exhibitions, which means:
- You’ll likely see something new each time you visit
- Displays can be surprising, playful, and thought-provoking
- You don’t need to be an art expert to enjoy it
It’s a nice indoor activity for a rainy day or a cold winter afternoon. The building itself, a former train station, adds to the charm. Many visitors combine a museum stop with lunch or coffee downtown for a simple but satisfying day in Brattleboro.
7. Paddle the Connecticut or West River
For a different view of the area, get out on the water. Near West Brattleboro, you can kayak, canoe, or paddleboard on the
Connecticut River or sections of the
West River.
Depending on your experience level, you might:
- Rent a kayak or canoe from a local outfitter
- Bring your own gear if you have it
- Join a guided trip for extra safety and local knowledge
On a calm summer morning, paddling along the river with mist lifting off the water feels almost unreal. You may see herons, ducks, and other wildlife along the banks.
Always check water conditions and weather before heading out, and wear a life jacket. Rivers can change quickly with rain and snowmelt.
8. Take a Scenic Drive Through Windham County
Sometimes the best thing to do in Vermont is just… drive.
From West Brattleboro, you can enjoy classic
New England scenic drives along winding back roads lined with farms, forests, and small villages. In the fall, this area becomes a patchwork of bright colors you’ll want to pull over and photograph every few miles.
Consider heading toward:
- Newfane – a postcard-perfect village with a white church and town green
- Putney – another artsy town with farm stands and local shops
- Guilford – quiet country roads and old cemeteries with early Vermont history
If you’re coming from the city, the slower pace and open space can feel like a deep breath for your brain.
9. Catch a Show or Event at the Latchis or Local Venues
Brattleboro has a surprisingly active arts and performance scene for a small town.
One highlight is the historic
Latchis Theatre, a downtown Art Deco gem that hosts:
- First-run movies
- Film festivals
- Special events and live performances
Around town you’ll also find small music venues, coffeehouses with live performances, and community theaters. If you like planning ahead, check local event listings before your trip to see what’s happening while you’re in West Brattleboro.
There’s something special about seeing a show in a small Vermont town, then stepping back out onto a quiet main street under a sky full of stars.
10. Enjoy a Cozy Vermont Stay and Local Eats
Part of the charm of visiting West Brattleboro and the Brattleboro area is slowing down and just… being there.
Consider:
- Booking a local inn, bed and breakfast, or farmhouse stay
- Trying a couple of different restaurants that focus on local ingredients
- Relaxing on a porch or patio with a book and a cup of coffee
You’ll find restaurants and cafés nearby that serve Vermont cheeses, seasonal veggies, and of course, maple-inspired desserts. Many spots are casual and welcoming, with friendly staff who are happy to talk about the area.
Sometimes the best “thing to do” in West Brattleboro is nothing big at all—just enjoying a slower pace, good food, and fresh air.
Planning Your Trip to West Brattleboro, Vermont
Here are a few quick tips to make your visit smoother:
- Best time to visit: Summer and fall are ideal for hiking and foliage. Winter brings snow and a cozy feel. Spring is quieter but can be muddy.
- Getting around: A car makes it much easier to explore West Brattleboro and Windham County.
- What to pack: Layers, comfortable walking shoes, and a light jacket—even summer evenings can be cool.
Whether you’re into outdoor adventures, local food, small-town shopping, or just need a peaceful reset,
West Brattleboro and the Brattleboro area offer plenty to fill a weekend (or more) without feeling rushed.
What Would You Do First Near West Brattleboro?
Have you been to West Brattleboro or Brattleboro before? Did you hike Wantastiquet, browse the downtown shops, or discover a hidden-gem café?
I’d love to hear about your favorite things to do in southern Vermont.
- Drop a comment below and share your tips or questions.
- If you found this guide helpful, please share it with a friend who’s planning a Vermont trip!
Your stories and suggestions can help other travelers make the most of their own visit to West Brattleboro, Vermont.
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