Top 16 Best Things to Do in Brattleboro Vermont

You’ll find plenty of things to do in Brattleboro VT, a small town bursting at the seams with activity. Between its bustling downtown, thriving arts scene, local food, and outdoor recreation you may not know where to begin.

A photo of downtown Brattleboro Vermont

Bordering New Hampshire to its east and mere miles away from Massachusetts to its south, Brattleboro Vermont is a small town that’s often overlooked by more cosmopolitan Burlington, and ski towns like Stowe. But for a town of just over 11,000 people, Brattleboro has an enormous number of things to do year-round.

Downtown Brattleboro is where you’ll find much of the action, including museums, a theater, and a variety of independent stores and art galleries. It’s here where you’ll also find the town’s plethora of Vermont-made foods showcased in its co-op and restaurants. And downtown is also the place where the Amtrack train pulls into the station.

Just a few miles outside of town is where other arts venues and outdoor recreation occur such as canoeing, kayaking, hiking, and camping. You’ll also find the town’s world-famous ski jump out here as well as a unique farm that welcomes visitors and hikers alike.


16 of the Best Things to do In Brattleboro VT

Whether you’re just passing through for the day or staying overnight, here are 16 of the best ways to spend your time in Brattleboro.

Wander through downtown Brattleboro

A photo of downtown Brattleboro Vermont at night. Wandering through the downtown is one of the things to do in Brattleboro VT.

With a population of only 11,000 people, you’d be forgiven for assuming Brattleboro is a bit sleepy. But on any given day Brattleboro’s downtown is hopping with activity. This community’s center is full of red brick buildings, many of which date back to the 19th century, and a wide variety of shops, restaurants, bookshops, and speciality stores.

In addition to the Co-op, there’s also Everyone’s Books which carries a range of titles and hosts frequent author events. There’s also Vermont Artisan Designs that features handcrafted items including pottery, jewelry, and furniture. And don’t forget the beloved Sam’s Outdoor Outfitters, a family-run outdoor store that’s been in Brattleboro since 1932.

If your wander extends into lunchtime, be sure to check out the Vermont Country Deli where you’ll find the typical deli fare as well as Vermont-made cheeses, jams, and, of course, maple syrups.

Visit the Brattleboro Museum & Art Center

The front of The Brattleboro Museum & Arts Center. It's one of the things to do in Brattleboro VT.
The Brattleboro Museum & Art Center is in the town’s former Union Station, built in 1915. Photo credit: Beyond My Ken/ Wikimedia

If you’re interested in art, one of the top things you’ll want to do in Brattleboro VT is visit the Brattleboro Museum & Art Center (BMAC). Housed in the town’s converted Union Rail Station, this non-profit hosts a variety of contemporary art exhibitions throughout the year featuring work by local, regional, and nationally-recognized artists using a wide range of media. A recent exhibit featured subway drawings by Keith Haring and works from the Vermont Glass Guild, among others.

In addition to exhibits, you’ll also find a range of educational programs and events, including lectures, artist talks, and workshops for kids and adults. There’s also a gift shop within the museum that sells art-related merchandise and a small cafe. Admission: “Pay as you wish” with a suggested donation of $5-$10 per adult. Hours: Wednesday-Sunday 10 AM – 4 PM. (10 Vernon Street)

Explore the Brattleboro Food Co-op

The inside of the Brattleboro Food Co-op
Photo credit: liz west/ Flickr

If you’re looking for a quick bite to eat or just enjoy exploring food markets, be sure to stop by the Brattleboro Food Co-op. Founded in 1975, this co-op is a community-owned grocery store located in the center of town. Inside, you’ll find a wide selection of natural, organic, and locally sourced food products as well as household and personal care items. If you’re in the mood for a quick lunch, check out the Co-op’s deli that offers prepared foods, sandwiches and salads, and also a cafe that serves coffee, tea, and baked goods. Although the Co-op is run by members, it’s open to everyone. Open 8 AM – 8 PM, Sundays open at 9 AM. (2 Main Street)

See related: 10 New England Small Towns That Feel Like Stars Hollow

Visit the unique Retreat Farm and hike its trails

About four minutes up the road from downtown Brattleboro is Retreat Farm, a unique property encompassing 500 acres of conserved forests, farmlands, trails, and waterways that’s open to the public. Kids will enjoy visiting goats, ox, and donkeys in the pasture as well as playing on the forest playground and walking along the storyboard walk.

Retreat Farm is also the start of five trailheads that make up the nine-mile Retreat Trails. This network of trails for hikers, bikers, horseback riders, and skiers covers more than 400 acres of forest and agricultural land and crosses a few interesting sites like the old cemetery and Retreat Tower. (45 Farmhouse Square)

Cross the Creamery Covered Bridge

A photo of the Creamery Covered Bridge in Brattleboro VT

Another fun thing to do in Brattleboro VT is to visit the town’s last remaining 19th-century covered bridge, the Creamery Covered Bridge. This red beauty formerly connected traffic on Guilford Road across Whetstone Brook. While today the bridge can only be crossed by foot, it’s still worth the short trip from downtown to travel back in time or to take a photo. (500 Western Avenue or 3 Guilford Road)

Learn about sugaring at the Robb Family Farm Sugar House

A short 15-minute drive west of downtown Brattleboro will take you to the Robb Family Farm Sugar House. Here, you’ll be able to shop the gift store for a range of maple products including maple syrups and candies. It’s possible that you may even get a tour of the farm and learn about its 100-year-old history with roots in the dairy business and how sap is turned into syrup. (822 Ames Hill Road)

Paddle down a river at the Vermont Canoe Touring Center

A woman canoeing down a river

If you love being out on the water, then you’ll want to head over to the Vermont Canoe Touring Center in southern Brattleboro. Here you’ll be able to rent canoes, kayaks, or stand-up paddleboards to ride on the West or Connecticut River. Both these rivers typically have calm waters, making paddling possible for all experience levels. Rates are between $20 for one hour and $60 for a full day depending on the craft. Hours: typically open between noon – 5 PM during warm weather months. (451 Putney Road, Route 5)

Let kids have time to play at the KidsPLAYce

A fun thing for kids to do in Brattleboro is to visit KidsPLAYce, an indoor play space for children ages birth to 8 years. The space is located underneath Hotel Pharmacy and essentially provides a place for kids to let loose and dive into imaginative play. KidsPLAYce features a life-size castle, pirate ship, townhouse, train, craft center, and other fun activities. Admission is $5 per child ages 1-8. During the summer KidsPLAYce is only open on Fridays from 10 AM – 2 PM. From September 23rd – May it’s open Tuesday-Saturday 10 AM – 2 PM. (20 Elliot Street)

Hike, camp, and explore at Fort Dummer State Park

Outdoors enthusiasts will want to head over to Fort Drummer State Park to hike, camp, or just have a picnic. While this park isn’t technically in Brattleboro, it’s just across the southern border of the town. Fort Drummer includes 217 acres of forest with short hiking trails that cover the park, including one that leads to a swimming hole. The onsite campground has 50 tent or trailer sites and 10 lean-to sites served by two toilet buildings with coin-operated showers. (517 Old Guilford Road, Guilford, VT)

Pick up some Vermont cheese at Grafton Village Cheese

The Grafton Village Cheese store in Brattleboro Vermont. Visiting the store is one of the things to do in Brattleboro VT
Photo credit: Theresa O’Connor / Flickr

After your visit to Retreat Farm, stop in at the Grafton Village Cheese Farm next door. All cheeses are handmade from raw milk collected from small family farms and the specialty cheese is cheddar. You can find Grafton Village cheese at groceries and food stores throughout New England but this is its only retail space. (400 Linden Street, Route 30)

Listen to world-class musicians at the Vermont Jazz Center

If you’re a jazz enthusiast, be sure to check out the Vermont Jazz Center. Located in Brattleboro’s Cotton Mill Hill Complex, the center includes a 250-seat performance hall featuring regular performances as well as an archive/library and educational opportunities. Featured musicians at the center have also played at Lincoln Center, the Kennedy Center, and the Village Vanguard. Check the center’s website for upcoming performances. (72 Cotton Mill Hill)

Catch a show at the Latchis Theater

The front of the Latchis theater in Brattleboro VT

The Latchis Theater, built in the 1930s, is a popular destination for movie-goers and live performance enthusiasts in Brattleboro. It hosts a variety of films, concerts, and other events throughout the year. For example, you can catch the latest New England Center for Circus Arts (located in Brattleboro!) Circus Spectacular or a streaming broadcast of the Metropolitan Opera. (50 Main Street)

Play to your heart’s content at the Estey Organ Museum

If you’re an organ enthusiast, you’ll want to check out the Estey Organ Museum dedicated to the music and instruments produced by the Estey Organ Company. Inside the museum, you’ll find memorabilia and instruments representing the 100-year history of this company and its contributions to southern Vermont. Visitors are encouraged to bring their own music and play the museum’s reed and pipe organs. Admission: Non-members requested to donate $5. Hours: Saturdays, May – mid-October from 2 PM – 4 PM. (108 Birge Street)

Fun Events to Do in Brattleboro VT:

The following things to do in Brattleboro VT include fun and unique seasonal events to keep on your radar!

Pick up some local food at the Brattleboro Farmer’s Market

Produce at the Brattleboro Farmer's market
Produce at the Brattleboro Farmer’s market. Photo credit: Pat Yeaman / Flickr

If you’re visiting Brattleboro on a Wednesday or Saturday during warm weather months, a stop at the Brattleboro Farmer’s Market is worth a visit to check out local meats, produce, and dairy products, arts and crafts, and listen to a little live music. This market typically features over 50 vendors and will expose you to a wide range of foods Vermont is known for. The market is held on Wednesdays and Saturdays, May – October, from 9 AM to 2 PM. You’ll find the Sunday market by the Creamery Bridge (500 Western Avenue) and the Wednesday market on the Whetstone Pathway off Main Street, not far from the Brattleboro Food Co-op.

Watch skiers fly through the air at the Harris Hill Ski Jump

A photo at the Harris Hill Ski Jump in Brattleboro Vermont.
The Harris Hill Ski Jump. Photo credit: Jared and Corin/ Creative Commons

One of the more exciting events in Brattleboro VT is the annual ski jumping tournament at the Harris Hill Ski Jump. This event began in 1923 and attracts thousands of spectators every year. The jump was first constructed in 1922 and is an Olympic-calibre 90-meter length, making it one of the tallest in the United States. Over the years, the Harris Hill jump has hosted 9 national championships and the Olympic Qualifier events. The tournament typically takes place during the last weekend in February. (Cedar Street)

See a performance with the N.E. Center for Circus Arts

A performer from the New England Center for Circus Arts
A performer from the New England Center for Circus Arts. Photo credit: Matthew Ragan/ Flickr

Just when you thought this small town had everything, you discover that it has a school to teach circus performers! While a visitor can’t just walk into the New England Center for Circus Arts to watch what they do, you can check out the center’s Circus Spectacular and other events it holds every year. The Circus Spectacular showcases the school’s most renowned high-flying aerialists, acrobats, and jugglers and typically takes place at the beginning of March at the Latchis Theater in downtown Brattleboro. (Center’s address: 10 Town Crier Drive)

FAQ about Brattleboro VT:

Is Brattleboro worth visiting?

Brattleboro is definitely worth visiting while you’re in Vermont! It’s incredible how many things there are to do in this small town. And Brattleboro’s downtown with its historic red brick buildings seems to always be bustling with activity. It’s the perfect place for a day trip or to spend a night or two taking part in local activities or events.

What is Brattleboro known for?

Brattleboro is known for its small-town charm with big-world appeal. The arts scene in Brattleboro is expansive from visual arts at the Brattleboro Museum & Arts Center to world-class jazz at the Vermont Jazz Center to The New England Center for Circus Arts. Brattleboro is also known for its local organic food scene with both its Food Co-op and restaurants, and a wide variety of independent stores to explore. And for outdoor enthusiasts, there are plenty of hiking, camping, canoeing, and kayaking opportunities.

Is Brattleboro a hippie town?

That depends on how you define “hippie”. Brattleboro, like many towns in Vermont, has a progressive vibe to it. You’ll see this sentiment reflected in stores, signs, and in the residents themselves.

What is there to do in Brattleboro in the winter?

Vermont in the winter can be magical with snow on the ground and sprinkled on the trees. And interior spaces are cozy with a glowing fire in the fireplace and hot chocolate in hand. Visitors to Brattleboro can cross-country ski and snowshoe along wooded trails and skaters appear on Retreat Meadows once the ice is the right thickness. You can also venture over to the  Harris Hill Ski Jump to see skiers fly through the air. And downhill skiing is only a few minutes away at Mount Snow, the Maple Valley Ski Area, or the town’s own small slope, the Brattleboro Ski Hill.

A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has spent the past 26 years living in New England. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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