Top 15 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 need help knowing where to begin.

Downtown Brattleboro, Vermont

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

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

Just a few miles outside of town, 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 and a unique farm that welcomes visitors and hikers alike.

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15 of the Best Things to Do In Brattleboro VT

Whether you’re just passing through for the day or staying overnight, here are the 15 best ways to spend your time in Brattleboro.

Wander through downtown Brattleboro

Wandering through downtown is among the things to do in Brattleboro VT

With 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 specialty stores.

In addition to the ever-popular Co-op (see below), there’s also Everyone’s Books, which carries a range of titles and hosts frequent author events. Vermont Artisan Designs also features handcrafted items, including pottery, jewelry, and furniture. 

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

Visit the Brattleboro Museum & Art Center

The outside of the Brattleboro Museum and Arts Center
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 various 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 $5-$10 donation per adult. Hours: Wednesday-Sunday 10 AM – 4 PM. (10 Vernon Street)

Explore the Brattleboro Food Co-op

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

If you want a quick bite to eat or enjoy exploring food markets, stop by the Brattleboro Food Co-op.

Founded in 1975, this co-op is a community-owned grocery store in the town center. Inside, you’ll find a wide selection of natural, organic, and locally sourced food products and household and personal care items.

If you’re in the mood for a quick lunch, check out the Co-op’s deli, which offers prepared foods, sandwiches, salads, and a cafe serving coffee, tea, and baked goods.

Although members run the Co-op, 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

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

Retreat Farm is also the start of five trailheads that comprise 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. It crosses a few interesting sites like the old cemetery and Retreat Tower. (45 Farmhouse Square)

Cross the Creamery Covered Bridge

Walking across the Creamery Covered Bridge is among the things to do 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 only pedestrians can cross the bridge today, it’s still worth the short trip from downtown to travel back in time or take a photo. (500 Western Avenue or 3 Guilford Road)

See related: The Creamery Covered Bridge: What You Need to Know Before Visiting

Learn about sugaring at the Robb Family Farm Sugar House

A 15-minute drive west of downtown Brattleboro will take you to the Robb Family Farm Sugar House. Here, you can shop the gift store for maple products, including maple syrups and candies.

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 sitting in a canoe on the water with her oar in the water

If you love being out on the water, you’ll want to head to the Vermont Canoe Touring Center in southern Brattleboro. You can 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 and 5 PM during warm weather months. (451 Putney Road, Route 5)

Hike, camp, and explore at Fort Dummer State Park

Outdoors enthusiasts will want to head to Fort Drummer State Park to hike, camp, or picnic. While this park isn’t technically in Brattleboro, it’s just across the town’s southern border.

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 ten lean-to sites served by two toilet buildings with coin-operated showers. (517 Old Guilford RoadGuilford, VT)

Pick up some Vermont cheese at Grafton Village Cheese

Visiting the Grafton Village Cheese store is among the things to do in Brattleboro VT
Photo credit: Theresa O’Connor / Flickr

After you visit 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.

Grafton Village cheese is available at grocery and food stores throughout New England, but this is its only retail space. (400 Linden Street, Route 30)

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Listen to world-class musicians at the Vermont Jazz Center

If you’re a jazz enthusiast, check out the Vermont Jazz Center.

The Center is located in Brattleboro’s Cotton Mill Hill Complex and includes a 250-seat performance hall featuring regular performances, an archive/library, and educational opportunities.

Featured musicians at the Vermont Jazz 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 outside of the Latchis Theater

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 music and play the museum’s reed and pipe organs.

Admission: Requested donation for non-members is $5. Hours: Saturdays, May – mid-October from 2 PM – 4 PM. (Check the website to confirm times and prices) (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 Vermont 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 occurs 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

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 nine 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

The New England Center for Circus Arts in Brattleboro VT
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 it has a school to teach circus performers!

While visitors 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 annual events.

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. (The 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 always to be bustling with activity. It’s the perfect place for a day trip or a night or two participating 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 its food co-op, restaurants, and various 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. This sentiment is reflected in stores, signs, and the residents themselves.

What is there to do in Brattleboro in the winter?

In the winter, Vermont can be magical, with snow on the ground and sprinkled on the trees. The 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 small slope, the Brattleboro Ski Hill.

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A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. 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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