13 Fun & Best Things to Do in Brattleboro, Vermont

Brattleboro is a town in Southern Vermont, well known for its local urban art scene, historic covered bridges, and quaint downtown area on the banks of the Connecticut River.

Brattleboro, Vermont, is a hot spot for travelers in all four seasons, and it’s understandable why. Spring and summer mean perfect weather, complete with hiking and biking trails, and a crisp fall offers apple cider, maple syrup, and craft beer as you watch the leaves change.

Winter brings some of the best cross-country skiing and the most beautiful snowfall to witness in New England. No matter what time of year you’re planning a trip, Brattleboro won’t disappoint.

For those new to the area, there are exciting things to do in Brattleboro for kids, families, outdoor enthusiasts, and everyone in between. Keep reading for the best places to visit and things to do in Brattleboro, Vermont.

The Covered Bridge Inn
1. The Covered Bridge Inn
Top Recommendation


Looking for a cozy, charming place to stay in Brattleboro? Look no further than The Covered Bridge Inn! This quiet, quaint inn is the perfect spot to relax and enjoy all that Brattleboro has to offer. The helpful staff and convenient location get high marks from guests, and the free WiFi and self-serve breakfast make it even more enjoyable. Whether you’re looking to stay active with some hiking or snowboarding, or just want to relax in a beautiful setting.

Comfort Inn Suites Brattleboro I 91
2. Comfort Inn & Suites Brattleboro I-91


Looking for a place to stay while you’re exploring the majestic Green Mountain Range? Then look no further than Comfort Inn & Suites Brattleboro I-91! This hotel is conveniently located off Interstate 91 and features free WiFi and free parking, making it the perfect place to rest your head after a day of exploring. All rooms come equipped with full size work desks, ergonomic chairs and coffee makers, so you can stay productive even while on vacation. And if you’re looking to stay fit and active during your trip, be sure to take advantage of the hotel’s fitness centre.

Holiday Inn Express Hotel Suites Brattleboro
3. Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel


Looking for a great place to stay in Brattleboro, Vermont? Look no further than Holiday Inn Express Hotel & Suites Brattleboro! This hotel offers free Wi-Fi, an indoor pool, and spacious guest rooms, making it the perfect place to relax and unwind. The Brattleboro Museum and Arts Center is just a 5-minute drive away, so you can easily explore all that the area has to offer. And when you’re ready to retire for the evening, you’ll appreciate the comfortable accommodations, complete with coffee facilities, a microwave, and a refrigerator.

TLDR

  • Most significant landmark – Harris Hill Ski Jump
  • Best park – Fort Dummer State Park
  • Best free activity – Creamery Covered Bridge
  • Best activity for kids – Retreat Farm
  • Best activity for adults – Saxtons Distillery
  • Best food – Whetstone Station Restaurant
  • Best nightlife – The Collective Lounge & Bar
  • Best all-around accommodation – Covered Bridge Inn

Best & Fun Things to Do in Brattleboro, Vermont

1. Brattleboro Area Farmers Market

Address: 570 Western Ave, West Brattleboro, VT 05301

Open every year from May to October, Brattleboro Area Farmers Market is one of the most iconic local events in town.

Every Saturday from 9 am to 2 pm, both locals and visitors gather near Guilford Street, right by the Creamery Covered Bridge, to browse the many vendor booths for local treasures, art, home decor, food, drinks, and more.

With over 40 full-season vendors, Brattleboro Area Farmers Market is award-winning, and for good reason. Featuring delightful goods to purchase, live music at lunchtime, and kid-friendly activities including a giant sandbox, there’s something to keep the whole family entertained for several hours.

Vendors sell artisan items like handmade crafts, candles, pottery, jewelry, soap, unique gifts, and more. Meet local and regional artists who sell their art at the market. Food vendors offer tasty treats like homemade pies, maple syrup, crepes, baguettes, pressed juice, chocolate, and many other delectable items.

Whether you’re in town alone, with friends or family, Brattleboro Area Farmers Market is a great place to spend a few hours, meet locals, and support small businesses in the area. You can grab a coffee or a pastry, wander the booths, and experience Southern Vermont culture firsthand. The farmer’s market is a seasonal must-see, and it’s one of the best free things to do in Brattleboro.

See Related: Fun & Best Things to Do in Bennington, Vermont 

2. Creamery Covered Bridge

Creamery Covered Bridge

Address: 500 Western Ave, Brattleboro, VT 05301

Creamery Covered Bridge is the only covered bridge left in Brattleboro that is visible from Route 9. It’s about 1.5 miles from downtown Brattleboro. This historic covered bridge was built in 1879 and is made from spruce lumber.

It’s a prominent scenic spot in Brattleboro because of its history in southeastern Vermont. The bridge is located just off Route 9 and spans the Whetstone Brook, which leads into the Connecticut River in Brattleboro. The bridge is listed on the National Register of Historic Places.

If you have an hour, be sure to make a stop at Creamery Covered Bridge for an interesting step into the past with a simple look at the historic covered bridge. It’s a pedestrian bridge only, so plan to park your car and walk to the bridge to check it out. 

There’s a small family-owned deli nearby where you can buy lunch and freshly baked pastries to enjoy a picnic outdoors.

Grab a few photos of the historic bridge, appreciate its architecture and history, admire the surrounding forested and hilly area, and be on your merry way. As one of the most popular Brattleboro tourist attractions, don’t travel all the way to Vermont and miss this historic site.

Looking for a hotel nearby? The Covered Bridge Inn is a six-minute drive from the Creamery Covered Bridge.

3. Brattleboro Museum & Art Center

Address: 10 Vernon St, Brattleboro, VT 05301

The Brattleboro Museum & Art Center presents rotating exhibits of contemporary art. The museum’s mission is to present art and ideas in ways that inspire, educate, and engage children and adults from all walks of life.

The Brattleboro Museum was founded in 1972 and offers frequently changing exhibits, programs, and public events that aim to engage the public through culture and community.

At the museum, guests can expect to see a wide array of art and creations from regional and international artists. You’ll see contributions from local student art, handblown glass creations, woven art, mixed media, and much more. The exhibits change regularly, so the surprise of what’s on display when you visit is all part of the fun.

Aside from its eclectic collection of art, the Brattleboro Museum is also home to many events throughout the year. These events include lectures, workshops, and performances that bring artists and culture to Brattleboro, Vermont, for its locals and visitors to experience firsthand.

The Museum & Art Center is located on Vernon Street, a historical building built in 1915, and locals have worked hard to keep the building standing and in great shape for visitors throughout the years.

Brattleboro Museum & Art Center participates in the local Gallery Walk, which takes place from May to December on the first Friday of each month. Visitors and locals explore the many art galleries in downtown Brattleboro, meet regional artists, and experience the talent of the area.

The museum and art gallery are open Wednesday through Sunday from 10 am to 4 pm.

See Related: Best Museums in the US You Need to Visit

4. Retreat Farm

Address: 45 Farmhouse Square, Brattleboro, VT 05301

Retreat Farm is a historic piece of land featuring nine historic barns, a grassy square, 10 miles of trails, and bodies of water for guests to enjoy. The farm is located on 500 acres of Abenaki homelands at the edge of downtown Brattleboro, Vermont. 

Visitors to the farm can explore the many walking trails; for families, we recommend the Nature Trail, a quick half-mile trail that is easy and fun for kids of all ages. You can see the farm animals, experience the new labyrinth path called Hope Garden and its many flowers and herbs, and explore many art installations in the area.

There is so much history to explore and learn about Retreat Farm, and helpful interpretive signs are sprinkled throughout the land, providing guests with details about the history and mission of the farm.

If you’re bringing the family, your kids will love interacting with farm animals, including goats, sheep, chickens, pigs, and an ox named Carlos. Children can experience one of the most hands-on farming experiences in the region at Retreat Farm.

There’s also a Forest Playground where kids can play and use their imaginations as they explore the farm and its many sights. Don’t miss a stroll through Storybook Walk, where children can search for diverse stories on a short, winding trail. Retreat Farm is free to visit and is open every day from dawn to dusk.

5. Harris Hill Ski Jump

Address: 264 Cedar St, Brattleboro, VT 05301

Harris Hill, the town’s ski jump, is one of the city’s most iconic landmarks. Since 1922, ski jumpers and fans of the sport have gathered in Brattleboro, Vermont, to witness the world-class skiing competition. If you’re fortunate enough to witness the Harris Hill Ski Jump Competition, you know what an incredible experience it is. 

The 90-meter ski jump sends skiers sailing 300 feet in the air at mind-boggling speeds of up to 60 miles per hour. Athletes from around the world compete in below-freezing temperatures and snowfall throughout the event.

For 100 years, Brattleboro has been home to this legendary sporting event. Although it only happens once a year, this Olympic sport is a Brattleboro tradition and one of the town’s most significant landmarks. 

In addition to the annual ski jump, Harris Hill hosts a few events throughout the year, typically during the snow season. Locals and visitors are invited to the park to ski, play in the snow, and learn about the exciting Olympic sport and what it takes to be that kind of athlete. Learn more about the Harris Hill Ski Jump and its 100-year anniversary here.

See Related: Best Holiday Destinations for Couples

6. Fort Dummer State Park

Address: 517 Old Guilford Rd, Guilford, VT 05301

Fort Dummer State Park is located on 217 acres of forest in the Connecticut River Valley, just outside Brattleboro, Vermont. Rich in history, Fort Dummer was the location of the first permanent European settlement in Vermont, beginning in 1724.

The park overlooks the original site of Fort Dummer, which was flooded when the Vernon Dam was built on the Connecticut River in 1908. A nearby marble monument commemorates the original Fort Dummer location. The site itself is now underwater but can be seen from the Sunrise Trail within the park.

Fort Dummer State Park is home to 50 RV and tent campsites, ten lean-to sites, on-site showers, restrooms, a small picnic area, and a dump station. The park is conveniently located close to downtown Brattleboro and food markets if you need supplies. Enjoy nights under the beautiful Vermont sky and make memories with your whole family at Fort Dummer.

Whether you’re camping for several nights or visiting for a few hours, you can enjoy abundant walking trails and a swimming hole. You may even catch a glimpse of some wildlife, including squirrels, turkeys, and deer.

Vermont state parks’ season is May to October, so plan accordingly if you’d like to see the state park while in Brattleboro.

7. Estey Organ Museum

Address: 108 Birge Street, Brattleboro, VT 05301

Estey Organ Museum is a historic Brattleboro museum that aims to celebrate the music and instruments produced by the Estey Organ Company, a local electronic organ manufacturing establishment that closed in the 1960s.

The mission of the Estey Organ Museum is to highlight the contributions of the Estey Company and its employees to Southern Vermont and to inform visitors about the town’s culture.

Located in Brattleboro’s Old Engine House, the museum commemorates the business makers of reed organs, pump organs, melodeons, and pipe organs. Visitors will see pipe organs from 1915, including the walk-through organ from Estey Organ Company and the Opus 1814, which was built in 1920.

As a hands-on museum, guests are encouraged to bring their own sheet music and perform on the reed and pipe organs. You’ll also see photographs of the Estey factory buildings and the talented workers that helped make Estey a household name.

Come and learn how the Estey Organ Company influenced the musical, industrial and social history of the 19th and 20th centuries. You can schedule a docent tour or explore on your own.

The Estey Organ Museum is open to visitors on Saturdays from May through October. A $5 donation is required upon arrival at the museum.

See Related: Fun & Best Things to Do in Stowe, Vermont

8. Whetstone Station & Brewery

Address: 36 Bridge St., Brattleboro, VT 05301

If you want to grab some food and visit a brewery, Whetstone Station Restaurant provides that and so much more!

The brewery sits right on the bank of the Connecticut River and has been a local favorite since its opening in 2012. It offers a great location with a laid back atmosphere and is a warm, welcoming, family-friendly restaurant and brewery for visitors and locals.

Owned by Brattleboro locals, Whetstone has an on-site brewery and a larger production brewery for its impressive selection of local craft beers. They have 14 in-house beers on draft at any time, designed for various palettes and cravings. Popular favorites include the Hazy Double IPA, Blood Orange Sour Ale, and the Amber Ale.

If you’re in the mood for good food, Whetstone is the place to be. Their menu features a burger station with free-range beef and chicken, where patrons can build their own burgers and sandwiches and choose from a wide array of sides and freshly prepared salads.

Aside from craft beer, Whetstone Station Restaurant has a few tasty cocktails, like a Paloma and a cranberry martini. They also have a wide selection of wines and soft drinks. When you arrive at Whetstone, you can dine inside or sit on the patio beer garden and enjoy some fresh air and a view of the picturesque riverside setting.

Aside from incredible beer and burgers, Whetstone Station Restaurant hosts community events that draw in crowds for the energetic environment and local feel. Events include live music performances, Open Mic nights, trivia, piano bar events, and much more.

Most events take place in the beer garden. If you’re on the hunt for the best food and beer in Brattleboro, you won’t be disappointed at Whetstone Station & Brewery.

9. Vermont Jazz Center

Address: 72 Cotton Mill Hill, Brattleboro, VT 05301

Brattleboro may not be known for its exciting nightlife scene; however, the town’s Vermont Jazz Center (VJC) hosts many musical performances and festivals that engage the community and its visitors.

As the leading jazz venue in New England, Vermont Jazz Center hosts many musical concerts in Brattleboro. Past events include the annual Jazz Piano Festival and an Emerging Artist Festival, among many others.

In addition to festivals, the Jazz Center features a summer jazz workshop, a monthly concert series, semester classes, and frequent collaborations with area schools, arts organizations, and businesses.

Vermont Jazz Center hosts jam sessions every Wednesday evening from 8 pm to 10 pm. Listeners and musicians of all skill levels are invited to join in on the magic. If you love jazz or just appreciate the local music scene in any city, be sure to check out Vermont Jazz Center for some of the most talented artists in the genre. 

VJC schedules concerts and performances up to a year in advance, so plan accordingly! 

See Related: Fun & Best Things to Do in Killington, Vermont

10. Wantastiquet Mountain Trail

For any adventure seekers visiting Vermont, Mount Wantastiquet is a must-see.

The easiest access point for this trail coming from Brattleboro is togo east across the bridge into New Hampshire, then turn left/north on Mountain Rd.

Spend the perfect day outdoors, breathing in the fresh mountain air and experiencing Vermont in all its stunning glory from the gorgeous hiking trails.

The Wantastiquet Mountain Trail is just under 4 miles and should take hikers around two hours to complete. As you explore the hiking trails, you’ll come across a natural waterfall near the trailhead, a thick and lush forest to enjoy as you walk, and a variety of other trails you can take along the way.

Mount Wantastiquet is about 1,335-feet high and its summit will take your breath away with the most scenic, panoramic views. From the summit at Miner’s Ledge, you’ll be able to see Mount Monadnock, the Connecticut River Valley, Brattleboro, and the Stratton Mountains in the distance.

If you’re looking for other hiking trails in the area, be sure to check out the trails within Madame Sherri Forest, along with other conservation trails in the area.

11. Saxtons Distillery

Address: 155 Chickering Drive, Brattleboro, VT 05301

Saxtons Distillery is a locally sourced small batch spirit distillery in the heart of Brattleboro. Some of Saxtons’ specialty liquors include Sapling Maple Liqueur, Sapling Maple Bourbon, Sapling Maple Rye, and Snowdrop Gin.

The maple syrup used in Saxtons’ specialty maple liqueurs comes from just ten miles away, and a local coffee shop supplies the dark roasted beans for the Perc Coffee Liqueur, one of the more popular spirits on the menu.

Since Saxtons’ opening in 2006, the establishment has focused on combining old-world heritage with Vermont’s classic taste and culture. The owner and head distiller gained an appreciation for maple syrup while living in Vermont and visiting the sugar houses. He was inspired to put the same amount of effort, care, and craftsmanship into his spirits.

Saxtons offers free tastings in its quaint tasting room and also sells liquor and merchandise at the distillery, including cool gift items like hot sauce and maple syrup. Sit at the bar and enjoy a sample or relax in the warehouse setting. Guests love the homey feel of the distillery and stay for the knowledgeable staff and high-quality libations.

Saxtons is open Monday through Saturday and is closed Sunday. Need a place to stay near Saxtons? Check out Holiday Inn Express just a few doors down.

See Related: Best Cheap Places to Travel in the US

12. Retreat Trails

Address: 45 Farmhouse Square, Brattleboro, VT 05301

Located on Retreat Farm in Brattleboro, Retreat Trails is an expansive 10-mile trail network that is free and open to the public for daily use.

From the farm, hikers can access the trail network from five different hiking trails to explore as much or as little as they want. The trails include the Nature Trail, Ice Pond, Woodlands Interpretive Trail, and Stone Tower.

The skill levels range from basic to advanced in Retreat Trails; you can take it easy and wander through the woods and winding trails, or take it up a notch and try to climb the stairs to the top of the Harris Hill Ski Jump. Whatever you’re in the mood for will be the perfect hike for you!

The Woodlands Interpretive Trail is a moderate one-loop trail that is well-loved by the community and popular with tourists. You’ll learn interesting facts about your surroundings thanks to a few placards placed along the trail. The Brattleboro Historical Society created this special trail network in the 1800s and it has served as a public resource for the community for over 200 years.

Whether you’re looking for a challenging hike or a relaxing stroll amongst the gorgeous Vermont scenery and surrounding countryside, you’ll check either box at Retreat Trails.

13. The Collective Lounge & Bar

Address: 55 Elliot Street, Brattleboro, VT 05301

Located in the heart of downtown Brattleboro, The Collective Lounge & Bar welcomes locals and visitors to come and relax with a beer, unwind after a long day, and enjoy the company of new friends.

If you show up hungry, the Tex-Mex snack menu will satisfy your hunger and help you avoid too bad of a hangover tomorrow.

Along with tasty snacks and craft beer, The Collective serves up some delicious craft cocktails for their customers. You’ve got to try the Coco Loco Margarita, Smoke ‘n Dagger, or any of their delicious mocktails if you aren’t in the mood for alcohol.

If you’re in town for more than a few nights, don’t miss the Open Mic Nights on Mondays, live music on Fridays, and $5 well drinks on weekdays, just to name a few. The Collective offers many opportunities for visitors to get a feel for the local watering hole and make some great friends along the way.

Tuck the kids in for the night and head out for a night of cocktails and shenanigans, Vermont style. The Collective is open seven days a week from 4 pm to midnight and til 2 am on the weekends. 

See Related: Fun & Best Things to Do in Burlington, Vermont

FAQ

What is the best thing to do with kids in Brattleboro, Vermont?

See one of the historic bridges in the area, the Creamery Covered Bridge. Explore Retreat Farm and meet the farm animals, or hike the Nature Trail at Retreat Trails. Learn about the history of historical musical instruments at the Estey Organ Company Museum. Spend a few hours at the Farmers Market, enjoying local food and shopping for unique gifts.

What are some fun things to do in Brattleboro, Vermont?

Explore downtown Brattleboro and its unique shops, art galleries, and great restaurants. Hike the Wantastiquet Mountain Trail and enjoy the stunning views from the summit. Explore Fort Dummer State Park and go for a swim. Get an authentic look at farming at Retreat Farm. Visit the history museums for a fun, educational experience.

What are some things to do in Brattleboro, Vermont, when it’s raining?

Sit inside and grab a beer at Whetstone Station. Watch a live jazz concert at Vermont Jazz Center. Learn about contemporary and traditional art in the area at Brattleboro Museum & Art Center. Taste locally sourced craft liqueurs, like maple bourbon, at Saxtons Distillery.

What are the best tourist attractions in Brattleboro, Vermont?

Harris Hill Ski Jump is an iconic tourist attraction in Brattleboro, Vermont. The Retreat Trails draw crowds from all over the country. Brattleboro’s Farmer’s Market is award-winning and is right down the street from the noteworthy Creamery Covered Bridge.

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