17 Fun Things to Do in Brattleboro, VT (Food, Art, and the Outdoors)
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There’s only one Brattleboro in this big wide world, and it’s tucked away in southeastern Vermont on the banks of the Connecticut and West Rivers.
With just over 12,000 residents, Brattleboro is a small town with urban flair.
The Abenaki people called the area Wantastiquet, which means ‘Lost River’, ‘River of the Lonely Way’, or ‘River that Leads West’. The town was chartered as Brattleborough in 1753 and grew into a mill town before becoming a vibrant commercial hub.
Modern-day Brattleboro is an oasis of art galleries, music venues, boutique shopping, and farm-to-table restaurants.
We live just an hour from Brattleboro, and it’s one of our favorite spots for a weekend getaway or adventurous day trip.
Want the inside scoop? Here are some of our favorite things to do in Brattleboro, VT.
Table of Contents
At-A-Glance: Brattleboro, Vermont
TL, DR: Want to skip to the good part? Here’s a bite-sized snapshot of everything you need to know to plan your trip to Brattleboro, VT.
- When to Go: Because Brattleboro has such a vibrant, walkable downtown, it’s a year-round destination, but May through October is best for outdoor experiences.
- Where to Stay: We love staying at the Latchis Hotel so we can walk to dining and shopping. This historic downtown hotel is pet-friendly and affordable.
- How to get here: If you aren’t within driving distance, we recommend flying into Bradley International Airport (BDL) in Hartford, CT, approximately 63 miles (about 1 hour 15 minutes) south of Brattleboro. Amtrak’s Vermonter runs from Washington, D.C., and NYC to Brattleboro and up through Vermont.
- How to Get Around: Brattleboro is very walkable, so it’s possible to explore without a car, but some attractions are farther than a walk from downtown.
- Top 3 Highlights: The trails, animals, and events at Retreat Farm, concerts at the Stone Church, and lunch at Yalla.
Explore the Shops in Downtown Brattleboro
Brattleboro’s Main Street feels like it belongs in a much larger town. There are enough distinctive shops, galleries, and restaurants within walking distance of downtown to fill multiple days of retail therapy and foodie adventures.
From the seemingly endless antique emporium, Twice Upon a Time, to smaller boutiques like the vintage clothing and apparel shop, Boomerang, Brattleboro has a veritable avalanche of options for the avid shopper.
We often spend large chunks of our time downtown in and out of two excellent bookstores just off Main Street. Everyone’s Books, which had a particularly well-curated section on history, politics, and current events, and Brattleboro Books, which boasts a massive collection of used manuscripts in every genre imaginable.
Visit Retreat Farm
Retreat Farm has been a mainstay in the Brattleboro community since its founding in the 1830s. Encompassing 500 acres of conserved forests, farmlands, trails, and waterways, Retreat Farm is a gathering spot for the community and an oasis of rural living.
Retreat Farm seems to offer something to appeal to any interest, from the farm’s rich history, with its lovingly preserved buildings, to its commitment to environmental justice and sustainability, to its celebration of farm-to-table cuisine, and, of course, all the farm animals. It’s impossible not to fall in love with Retreat Farm.
If you happen to be visiting Brattleboro on a Thursday during the summer, make sure you stop by the farm for the famous Food Truck Roundup.
This outdoor celebration of great food and music features over a dozen food and drink vendors from the Brattleboro area and a live music lineup curated by the Stone Church. It’s an event that you won’t want to miss (but be sure to leave your dogs at home).
Hike a Trail at Fort Dummer State Park
Fort Dummer State Park is about a 10-minute drive from downtown Brattleboro. The park has several trail options for short day hikes, and the well-maintained campgrounds make it a great choice for visitors who want to avoid hotels and motels.
The campsites are spread out, giving campers ample privacy during their stay, and the three hiking trails are all within walking distance of the campground.
During our visit, we hiked the Sunrise Trail and the Broad Brook Trail. The Sunrise Trail was a mile loop through the woods and was fairly flat, making it a nice, relaxing walk.
The Broad Brook Trail, although a little shorter than the Sunrise Trail, was very steep and might prove challenging for novice hikers, but it offered a much more rewarding final destination: a small, picturesque swimming hole on Broad Brook.
Visit the Art Galleries
Downtown Brattleboro is packed with galleries where you can browse or purchase locally-made pieces.
During our recent visit, we stopped by Gallery in the Woods, which had some beautiful ceramic pieces alongside handcrafted jewelry, incredibly detailed felt animals, and a wide range of prints and original works from some of Vermont’s best contemporary artists.
We also paid a too-short visit to Harmony Collective Artist Gallery.
Harmony Collective felt more like a mini-museum, with hundreds of unique paintings hanging throughout the shop and central displays devoted to indescribable sculptures crafted using both traditional materials like clay and papier-mache, as well as used handbags, scrap metal, and recycled bottles and cans.
Although we only had the chance to explore two galleries during our recent stay, there were many more options to choose from, and you could easily spend a whole weekend in Brattleboro going in and out of different galleries.
Windham Art Gallery, The Artist’s Loft Fine Art Gallery, Vermont Artisan Designs, and Gallery in the Woods are all within walking distance of each other, and you can find even more options by venturing just a little way off of Main Street.
Check out Brattleboro Museum & Art Center
Located in the middle of downtown, Brattleboro Museum and Art Center, or BMAC, is an unforgettable addition to the wealth of artistry on display in Brattleboro.
The museum has six galleries that rotate exhibits every few months, so you can keep coming back to see new things each time you’re in town.
Admission to the museum is “pay-what-you-can”; a donation of $5-10 per person is recommended but not required.
Step Back in Time at the Creamery Covered Bridge
Creamery Covered Bridge is another addition to Vermont’s famous catalog of covered bridges and is the only one visible from Route 9. Constructed in 1879, this bridge is now closed off to traffic but remains open to pedestrians.
Its proximity to the Brattleboro Farmer’s Market and the Vermont Country Deli makes the Creamery Covered Bridge a popular destination for tourists, and we found that the grassy area beside the bridge was the perfect spot for an impromptu picnic.
Discover the Estey Organ Museum
The Estey Organ Museum was one of the biggest surprises of our recent trip to Brattleboro; it’s a small museum devoted to a fairly uncommon instrument, and the fact that the museum was only open for two hours a week meant we had pretty low expectations.
However, the Estey Organ Museum turned out to be one of our favorite destinations on our trip.
The museum is located inside the old factory buildings where Estey Organs were once made. The large slate buildings have since been renovated to house various businesses and apartments alongside the museum.
Inside, you’ll find dozens of organs and pianos on display.
Some organs are hooked up to electric power supplies, while others require a hand crank or foot pedals to be operated to produce any sound. Best of all, every instrument in the building is available for visitors to play.
Getting the chance to play antique organs was an absolute blast, even if we could only remember how to play Hot Cross Buns and Chopsticks.
Our favorite instrument was a traditional pipe organ with an open back which allowed you to literally go inside the instrument while someone else played, creating the ultimate surround-sound experience.
If the museum’s interactive aspect wasn’t enough, there was an abundance of interesting information to discover about the history of organ making in Southern Vermont.
The staff member who was working when we visited had encyclopedic knowledge of Brattleboro’s history, which gave context to the exhibits and made us want to stay for hours.
This museum is one of the best things to do in Brattleboro, VT, especially if you’re into musical instruments or the history of commerce in Southern Vermont, and it will be especially fun for pianists and organ players. Hours are 2-4 pm every Saturday from May through mid-October.
Check Out Live Music at Stone Church
The Stone Church is one of Brattleboro’s best-known and most loved destinations, and it’s easy to see why.
The church was renovated to create a unique venue for performers stopping in Southern Vermont, and the gorgeous Gothic architecture creates a performance space unlike any other in Vermont.
The Stone Church has hosted music legends like Don McClean and consistently brings in talented artists from New England and beyond.
The Stone Church has live music almost every weekend, with wildly varying genres. During our visit, there were concerts featuring a folk-punk band with heavy metal influences and a Caribbean funk duo.
The sheer number of concerts held at the Stone Church makes it pretty easy to find one that will fit your taste, but even if you’re not sure whether you’ll like the artist that’s playing while you’re in town, we still recommend checking them out; it’s a great way to explore new types of music, and the venue alone is well worth a visit.
Discover the New England Center for Circus Arts
The New England Center for Circus Arts (NECCA) is an institution based around the instruction and practice of circus arts. These include acrobatics, balancing, parkour, juggling, aerials, and much more.
NECCA offers frequent performances as well as classes and workshops for adults and children. Come for the amazing displays of balance and coordination, and stay for the knowledgeable instructors and state-of-the-art facilities!
Hang out at the Brattleboro Area Farmers’ Market on Saturdays
The Brattleboro Area Farmers’ Market is in serious competition for the best Farmers’ Market in Vermont, and once you get there, you’ll know exactly why.
If the overflowing parking lots weren’t enough of an indication of what is to come, the smells of spicy Thai food, deep-fried samosas, cheesy crepes, and savory tacos will assure you that you’re in the right place.
Besides an abundance of delicious food made with fresh ingredients, you can also pick up an assortment of beverages, from fruit smoothies that are blended to order right before your eyes, to strawberry lemonade and piping hot (or icy cold) coffee and tea.
Once you’ve made it through the gauntlet of tents selling fresh produce and serving food and drink (this took us quite a while, as I wanted to eat something from just about every tent we saw), you’ll realize that you’ve only just begun to scratch the surface of what this market has to offer.
Amongst the many vendors, you can find handcrafted jewelry, alpaca wool clothing, fresh fruits and veggies, baked goods in every shape and size, Vermont-made wine and spirits, soap, candles, honey, maple syrup, and much more.
We spent almost two hours wandering around the market, and I’m still convinced that we didn’t see everything, so make sure you give yourself plenty of time to explore.
Rent a Boat from the Vermont Canoe Touring Center
Being situated right on the banks of the Connecticut River, the longest river in New England, Brattleboro has a close relationship with the water, which is evident in the number of boaters you’ll see out on the river when you’re there.
If you’re feeling envious watching kayaks and canoes dip in and out of the little inlets and coves of the river, then it’s high time you join them.
Take a trip up the road from downtown Brattleboro to visit the Vermont Canoe Touring Center, where you can rent canoes, kayaks, and paddleboards to explore the waterways at your leisure.
Boats are rented in 1-, 2-, or 4-hour increments, or you can save yourself the trouble of tracking your time and just rent them for the entire day.
Catch a Show at Latchis Theatre
The Latchis Theatre is a historic movie theater and performance venue in downtown Brattleboro and is connected to the Latchis Hotel (more on that later). The building, which houses both the theatre and hotel, was built in 1938 in the Art Deco style, which was very popular at the time.
The Art Deco movement isn’t the only unique aesthetic choice on display at the Latchis; inside the theatre, you’ll find stunning Greek murals depicting mythological scenes.
The combination of classic Greek murals with Art Deco architecture is dubbed “Greco Deco” by the Latchis Theater website, and its one-of-a-kind aesthetic makes the Latchis one of those rare places that can only be fully appreciated in person.
The Latchis hosts current films, from popular blockbusters to smaller indie films, and serves as a venue for live events. The space can also be rented out for private events.w
Venture Over to Madam Sherri Forest in Chesterfield, NH
If you’re looking for a beautiful day hike during your visit to Brattleboro, consider paying a visit to Madam Sherri Forest, which is just a short drive across the New Hampshire border.
You’ll find several trail options to choose from with various difficulty levels. The Anne Stokes Loop Trail is a two-mile hike perfect for hikers who want a less intensive experience.
The trail offers a scenic view of Indian Pond at about 0.5 miles and also passes the ruins of Madam Sherri’s “castle,” a crumbling stone structure reminiscent of ancient castle ruins found across Europe.
For a more challenging hike, check out the Wantastiquet Mountain trail, a 3-mile round-trip that leads to a gorgeous overlook of the Connecticut River Valley, with Mount Monadnock rising in the distance.
Visit Scott Farm Orchard
Scott Farm Orchard is the ideal fall destination in Brattleboro.
During autumn, the expansive orchards overflow with enthusiastic harvesters who have come to celebrate Vermont’s state fruit and indulge in one of the Green Mountain State’s oldest and most well-loved traditions: apple picking.
The farm has two orchards, each with a wide variety of apples and two kinds of peaches. During the harvest seasons, visitors can come to pick their own fruit or choose from over 130 varieties of apples at the Farm Market.
Embark on a Connecticut River Byway Road Trip
Travel along 410 miles of the Connecticut River from one end of Vermont to the other on Vermont’s only designated National Byway.
The Connecticut River Byway is a three-state, 500-mile byway spanning the west and east shores of the Connecticut River, starting in Massachusetts and traveling north through both Vermont and New Hampshire all the way to the Canadian border.
It passes right through Brattleboro and is one of the most scenic drives in all of Vermont.
Where to Stay in Brattleboro
The Latchis Hotel was the perfect place for our recent stay in Brattleboro. It features the same Greco-Deco aesthetic we loved at the Latchis Theatre, giving it a grand historical feel.
Located right on Main Street, the hotel is within walking distance of all the best food and drink Brattleboro has to offer, although one doesn’t even need to leave the hotel to find some of the best things to do in Brattleboro.
Want a posh vacation rental with historical significance? Stay at Naulakha, the former home of Rudyard Kipling and a National Historic Landmark.
Much of Kipling’s original furniture remains, which means that guests can sit at the very desk where the famed author wrote The Jungle Book, Captains Courageous, and portions of the Just So Stories.
This fully furnished three-story house makes an enchanting family getaway for a special occasion.
Crazy Good Brattleboro Restaurants for Your Dining Pleasure
Yalla: This wonderfully addictive little eatery is one of the reasons I make the drive to Brattleboro over and over again. Serving Eastern Mediterranean specialties like falafel, hummus, homemade pitas, and a bunch of other delicacies. This is one lunch spot you absolutely have to add to your Brattleboro itinerary.
Amy’s Bakery Arts Cafe: We stopped into Amy’s for lunch on a whim and discovered yet another not-so-hidden gem on Brattleboro’s Main Street. Amy’s features a relatively small menu of sandwiches, soups, and salads, as well as fresh-baked goods, coffee, and tea. We loved the sourdough bread they used to make their sandwiches, as well as the mountain of toppings they packed between the slices.
Vermont Country Deli: Famous for its mac & cheese, we have never had a bad bite here, and it’s a great spot to pick up all of your picnic provisions!
Check out these incredible things to do in Brattleboro the next time you’re passing through the southeast corner of the state. You’ll love exploring this beautiful Vermont town.
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Gabriel Reed is from Bennington, Vermont, and a graduate of Keene State College with a degree in English. He currently works at the North Cascade Institute in Washington State. In his free time, Gabe enjoys spending time outdoors and pursuing his love for fantasy stories, medieval aesthetics, and grilled meats.
You forgot the world renowned Harris Hill Ski jump & the competition that draws athletes from around the world in a 3 day event.
Can you elaborate on your stay at the Latchis Hotel? I’ve heard it’s very outdated. But see mostly good reviews. Saw there’s new management and they’re updating. Would love to hear more.
As for “Poutine” we’ll share that with you 😄