21 Fun Things To Do In Brattleboro (VT)

Brattleboro, Vermont, is known for its modern urban feel but maintains its rural setting. It’s also home to the state’s arts scene, which features local and national artists.

Located in Southern Vermont, the town of Brattleboro is also known for its summer and winter activities.

It’s also home to various cultural institutions, such as the Art Center and the Tasha Tudor Museum. In addition to these, other popular areas of recreation include skiing, skating, hiking, and tennis.

The article highlights the fun things to do in Brattleboro (VT).

Where Is Brattleboro, Vermont?

Located in Vermont’s Windham County, the town of Brattleboro is officially known as a municipality situated near the Connecticut River and the West River.

According to the census performed in 2020, the town’s population was 12,184. It’s around 10 miles away from the Massachusetts state line.

The town has a total area of about 32.5 square miles. According to the census data, the vast majority of it is made up of land.

There are several satellite campuses of various educational institutions in the town, such as the Community College of Vermont.

Other notable institutions include the Vermont Jazz Center and the New England Circus Arts.

Things To Do In Brattleboro (VT)

There are various parks and recreation facilities in Brattleboro, which are ideal for families and individuals looking for a good time out.

It also has several restaurants and bars that are great for various activities, such as swimming, tennis, and baseball. Here are the best things to do in Brattleboro, Vermont;

1. Fort Dummer State Park

One of the most popular parks in the area is Fort Dummer State Park, located in the Connecticut River Valley.

This park features over 200 acres of forest land, and its unique fauna characterizes it.

This region is known for its unique forest, which is unlike the forests found in other areas in New England.

The best way to maximize your time at Fort Dummer State Park is by exploring its various trails.

One of these ends at a swimming hole, offering fantastic views of the original fort. After exploring the park, you spend the night under the stars in a tent. 

Address: This attraction is at 517 Old Guilford Road, Brattleboro, Vermont 05301.

2. The Retreat Farm

Photo by Putneypics via Flickr

This popular local organization that preserves and enhances the rural way of life in Vermont is the Retreat Farm.

This farm is a nonprofit center focused on education, conservation, and recreation.

It offers hands-on experiences for children and adults, such as playing with farm animals and learning about farming.

The farm also features a gift shop that’s filled with various souvenirs. In addition, it allows children to interact with farm animals and learn more about life in the area.

The farm is also home to one of the five Retreat Trail trailheads, designed for skiers, hikers, and horseback riders. 

Address: The Retreat farm is at 45 Farmhouse Square, Brattleboro, VT 05301.

3. Brattleboro Area Farmers’ Market

The local farmers market in the town of Brattleboro is known for its variety of products and services.

It features over 50 vendors that sell various agricultural products, such as fruits and vegetables, honey, and cheese.

In addition, this market is known for its live music and ethnic food from other countries.

Besides food, the market hosts various other activities, such as demonstrations and workshops.

The market in the town of Brattleboro is open every Wednesday and Saturday from 9 am to 2 pm.

It’s located near the Whetstone Pathway and the Creamery Bridge. The market on Saturday is situated just west of town. 

Address: The market is at Western Ave, West Brattleboro, VT 05301.

4. Retreat Trails

The Retreat Trails is located south of the Green Mountain National Forest. They’re a series of trails that run through the area’s hilly and forested terrain.

The trail system features over nine miles of hiking and biking trails. Some notable sites in the trail system include the Retreat Tower and the old cemetery.

5. Brattleboro Museum & Art Center

The Museum and Art Center in Brattleboro was founded in 1972. It showcases the works of international and regional artists, such as Andy Warhol, Chuck Close, and Wolf Kahn.

It also features exhibitions conducted by local schools and other community organizations.

The museum’s collection includes works by other prominent artists such as Janet Fish and Chuck Close. 

Address: This museum is at 10 Vernon St, Brattleboro, VT 05301.

6. Creamery Covered Bridge

Photo by Ron Cogswell via Flickr

The West Hill Covered Bridge in the town of Brattleboro is also known as the Crystal Springs Covered Bridge. It’s the only surviving example of this type of bridge in the region.

The bridge was constructed in 1879 and is named after the area’s famous creamery. It spans 80 feet long and 19 feet wide.

It features a single-span bridge supported by two timber lattice trusses. The bridge also has a covered sidewalk located on its eastern side. 

Address: This bridge is located at Guilford Street off Route 9 west, over Whetstone Brook, Brattleboro, VT 05301.

7. Brattleboro History Center

Photo by Beyond My Ken via Wikimedia

The History Center in the town of Brattleboro is dedicated to showcasing the various artifacts and items collected by the local historical society. It is dedicated to preserving the town’s heritage.

The History Center is located on Main Street and features various exhibits that explore the history of the Valley Fair.

It also features a variety of toys, model railroads, and other interesting items related to the agricultural industry in the area.

The museum is open to the public regularly during the Gallery Walks, held from 5–8 pm. 

Address: This Brattleboro History Center is at 230 Main Street, 3rd Floor.

8. Whetstone Station Restaurant and Brewery

A local restaurant known as the Whetstone Station is located on the waterfront property and offers a variety of creative and unique food and drinks.

It’s a short walk from downtown Brattleboro and features year-round outdoor dining.

The restaurant’s menu features a variety of traditional pub-style dishes, such as grilled sirloin tips and seasoned crab cakes. It also features a variety of lighter meals such as sandwiches and burgers.

The restaurant’s staff members are knowledgeable about local and craft beers, and they can be reached by appointment or on the first Sunday of every month for a guided tour. 

Address: This restaurant is at 6 Bridge Street, Brattleboro, VT 05301.

9. Top of the Hill Grill

Photo by duluoz cats via Flickr

The Top of the Hill Grill restaurant offers a variety of authentic pit barbecue food. It features various types of food such as chicken and beef sandwiches, pulled pork, and ribs.

It also features a wide range of sides and salad options. Prime cuts of meat are part of the restaurant’s menu, and various fresh vegetables and dressings can accompany them.

Vegetarians are also welcome to enjoy a variety of food options. The restaurant’s menu features a variety of non-meat and vegetarian dishes.

For an added taste, try the restaurant’s Mexican and Cajun favorites. 

Address: The Top of the Hill Grill restaurant is at Williamsville, VT 05362.

10. Twice Upon a Time

Twice Upon a Time is a family-owned business that sells a wide range of unique and vintage items.

The store is located in a former department store renovated to its original level. It has 10,000 square feet of space inside the building.

The Twice Upon a Time store is located in a different area and features a wide variety of products.

It can source various furniture, art, and home décor from over a hundred dealers. The facility also offers rental spaces and consignments. 

Address: This attraction is at 63 Main St. Brattleboro, VT, 05301.

11. KidsPLAYce : Southern Vermont Children’s Discovery Center

The KidsPLAYce is a family-friendly indoor play space that provides a fun and interactive environment for children from 0 to 8 years old.

It features a variety of interactive exhibits and displays designed to encourage exploration and creativity.

Some of the exhibitions featured at the facility include a life-sized castle and a pirate ship.

If you’re looking for something a bit different to do in the area, this is a great place to visit. 

Address: This beautiful attraction is at 20 Elliot St, Brattleboro, VT 05301.

12. Estey Organ Museum

Established in 2002, the Estey Organ Museum is dedicated to preserving the history of the company and its various products.

It was established in honor of Jacob Edward, who founded the company and its electronic and reed manufacturing facilities in Vermont.

The museum aims to provide a deeper understanding of the company’s heritage through its exhibits and collections. 

Address: The Estey Organ Museum is at 108 Birge Street, Brattleboro, VT 05301.

13. Dosa Kitchen

Leda Scheintaub is the owner of Dosa Kitchen, a food truck that serves South Indian food. Her creative menu is based on her recipes. 

Address: Dosa Kitchen is at Grafton Cheese Village, 400 Linden Street (on Route 30) in Brattleboro, Vermont.

14. Hermit Thrush Brewery

The Hermit Thrush Brewery is a small-batch brewery that specializes in barrel-aged fruit and Belgian-inspired beers.

It was founded in 2014 by Avery Schwenk and Christophe Gagne. Their creations have gained a reputation for their amazing wild and sour beer recipes. 

Address: The Hermit Thrush Brewery is at 29 High Street Suite 101C, Brattleboro, VT 05301.

15. T.J. Buckley’s Uptown Dining

T.J. Buckley’s is a family-friendly restaurant that serves organic food with a focus on local ingredients. 

The restaurant was originally built in 1925 and featured a restored dining car. 

Address: The T.J. Buckley’s Uptown Dining is at 132 Elliot Street, Brattleboro, VT 05301.

16. Saxtons Distillery

The Saxtons Distillery is located in Vermont, established by Christian Stromberg to preserve the traditions of his family, which are from Lithuania.

Its unique blend of old-world and local ingredients makes it an ideal choice for any occasion. 

Address: This distillery is at 155 Chickering Drive, Brattleboro, Vermont 05301.

17. Peter Havens

Over the years, Peter Havens has been one of the most popular establishments in the town of Brattleboro.

Gregg Van Iderstine and Thomas Dahlin established the restaurant. It offers a warm and welcoming atmosphere, excellent food, and exceptional service. 

Address: This restaurant is at 32 Elliot Street, Brattleboro, VT 05301.

18. The Robb Family Farm Sugar House

One of the most popular attractions in Vermont is the Robb Family Farm Sugar House.

This farm was originally a dairy farm, but in 2011, it started focusing on maple syrup production. 

Address: This attraction is at 822 Ames Hill Road, Brattleboro, Vermont 05301.

19. Super Fresh Organic Cafe 

The super fresh organic cafe is a vegan and vegetarian restaurant near the Connecticut River.

It’s the only establishment in southern Vermont that serves 100% vegan and vegetarian food. 

A visit to this cafe is certainly one of the fun things to do in Brattleboro, Vermont. 

Address: The Super fresh Organic Cafe is at 30 Main St. Brattleboro, VT.

20. Harris Hill Ski Jump

Since 1922, spectators have been coming to Harris Hill to watch some of the best jumpers in the world compete.

The facility features a 90-meter jump designed to give the athletes the necessary boost to get them airborne. The ski jump is also another fun thing to do in Brattleboro, Vermont. 

Address: This beautiful attraction is at Cedar Street, Battleboro, Vermont 05301.

21. 118 Elliot

118 Elliot is a creative arts center that offers various events and activities related to music, creative arts, and educational talks. It also features works of art on its walls. 

Address: This art center is at 118 Elliot Street, Brattleboro, Vermont 05301.

Best Time To Visit Brattleboro

The best time to visit Vermont Brattleboro is from May to September. According to the National Oceanographic and Atmospheric Administration, the best time to experience ideal weather in this town is from May to September.

How Much Does It Cost To Visit Brattleboro?

A seven-day trip to Brattleboro costs around $1659 for an individual, $3,300 for a couple, and $5,586 for a family of four. 

The average hotel room cost in the town is around $55 to $250 a night.