20 Best Things to Do in Brattleboro, Vermont

20 Best Things to Do in Brattleboro, Vermont

Brattleboro is a beautiful countryside town in southern Vermont with a rich cultural history. This artistic town is a four-season holiday destination offering picturesque views all throughout the year. Gifted with sprawling natural beauty, this town provides endless opportunities for a wide array of recreational outdoor activities, such as hiking, camping, paddle boarding, fishing, canoeing, swimming, skiing, snowboarding, and lots more. The several museums, galleries, festivals, and events at Brattleboro aim at celebrating the local culture of this vibrant and cheerful town.

Experience Life on a Farm

Brattleboro farm
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Spend a day at Retreat community farm to experience the agrarian way of life. This farm is open daily to visitors from sunrise to sunset and entry is absolutely free of charge. Visitors can play with the farm animals or watch the fruits, vegetables, and flowers grow. The farm is a home to piglets, cows, goats, ewes, lambs, bucks, sheep, does, donkeys and an ox. Retreat farm is also a perfect spot for a nice picnic. It is to be noted that the barns and buildings here are closed to the public. The farm is connected to a forest with several splendid hiking trails.

Walk in the Woods

Brattleboro forest
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The Retreat farm is connected to a trail-traversed forest. It is a network of 9 miles of invigorating hiking trails that cover over 600 acres of farm fields and forestlands. This is one of the top tourist attractions in Brattleboro. The trails are fairly easy and offer phenomenal views of the dense greenery of this countryside town. The views are equally breath-taking in every season.

The West River trail is a 36 mile hiking trail that runs parallel to the serene West River. It has astounding views all throughout the year. The tranquil atmosphere and the nature’s heavenly beauty is bound to soothe one’s soul. The river is enveloped by dense forests and the air feels so amazingly fresh. Mount Wantastiquet trail is a 4 miles hiking trail that covers over 500 acres of densely forested land. It features a waterfall, an Indian pond, wildlife, and endless greenery. The summit of this mountain has surreal panaromic views of the Connecticut river valley, Brattleboro, and distant mountains. This hike is slightly difficult but the mind-blowing views are totally worth it.

Watch a Show at Latchis Theatre

Latchis Theatre
Beyond My Ken / CC BY-SA

Latchis is a historic theatre with ornate Greco Deco architecture, located in downtown Brattleboro. This theatre is a prominent part of this town’s local culture and has been organising live performances and playing cinema for over 80 years. It is also a host to the town’s renowned film festival which takes place every year around October end or early November. The festival features a broad array of documentaries, short films, and movies from all over the world.  Latchis theatre forms a part of the famous Latchis Hotel.

Travel Back in Time at Estey Organ Museum

The Estey Organ Company was one the top organ manufacturing companies in the world between late 1800s to 1950s. It sold its premier quality reed, pipe, and electronic organs to various countries across 6 continents. This company was founded by Jacob Estey in Brattleboro during the 1850s. This museum exhibits its several collections of the Estey Company’s manufactured organs. Images of the company’s factory buildings, employees, catalogues, and business cards are also displayed here. The museum beautifully captures the Brattleboro town’s regional culture from the 19th to 20th century  and celebrates the Estey Organ Company’s rich history. It’s really awe-inspiring to see these larger-than-life antique musical instruments.

Beat the Heat

Connecticut River Brattleboro
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Swimming, kayaking, canoeing, fishing, paddle boarding, and tubing are popular recreational water sports in Brattleboro during summers. The Connecticut and West rivers provide great opportunities for such water based activities in this region. The rivers are crystalline and have gorgeous scenic views. There are various businesses all around the town providing the requisite rental watercrafts and protective gear. Enjoy a perfect summer day engaging in such recreational activities followed by a fun picnic.

Attend the Strolling of the Heifers

Every year crowds gather to attend this world-renowned annual parade and cow-fest of Brattleboro. It is a pre-summer tradition that is organised during the month of June each year with a new and unique theme. The parade features numerous heifers strolling down the streets of this town with the farmers.  It is a vibrant and colourful festival which includes live music, performances, famer’s breakfast, regional farm tours, exhibitions, and block parties. The fest also sometimes features camels, goats and, other animals. The motive of this parade is to promote home-grown products, innovation in agriculture, and sustainable living. It lets you catch a glimpse of the local culture of Brattleboro.

Explore Art at Brattleboro Museum and Art Centre

Brattleboro Museum and Art Centre
Beyond My Ken / CC BY-SA

It is a historic local railway station converted into a museum and art centre. It showcases contemporary art works by regional artists. This centre dates back to 1972 and is one of the tourist hotspots of this town. Being a non-collecting museum, it rotates its exhibitions quarterly. The principal objectives of this art centre and museum are to support and nurture the local art talent and create awareness of the town’s rich cultural history. The six galleries of this museum organise around 20 exhibitions annually. Visit this gallery and explore the captivating works of art.

Trip to Naulakha

Naulakha is a historical landmark which once used to be the home of  the world famous English novelist and Nobel Prize laureate, Rudyard Kipling. This house dates back to the late 1800s and still retains most of the original furniture belonging to the author. Kipling wrote several of his renowned works in this building, including The Jungle Book, The Seven Seas, The Just So Stories, and Captains Courageous. The building was named after the Naulakha Pavilion in Lahore. ‘Naulakha’ means nine hundred thousand rupees, which was the cost of constructing the pavilion. The house is located about 4 miles from Brattleboro and is frequented by tourists. The Kashmiri boat styled house has stunning views of the surrounding meadows. The property has been renovated and maintained to be made available for rent to visitors.

Play in the Snow

Brattleboro Snow
Felix Lipov / shutterstock.com

Enjoy the mesmerising views of the snow-covered town in winters. Indulge in skiing, snowboarding, ice-skating, cross-country skiing, and snowshoeing. Winters in Brattleboro are extremely fun. Rental snow shoes, skiing equipment, snowboards are available at various places all over town, such as Sam’s Outdoor Outfitters, Brattleboro Outing Club Ski Hut, and Burrows Specialised Sports.

Experience Jaw-dropping Performances @ NECCA

New England Centre for Circus Arts or NECCA is a well-known circus school located in Brattleboro. It hosts a multitude of shows, events, and workshops all year round. Their monthly show called Beta Nights features performances by the students as well as other residents of the town and entry is absolutely free. Flight Nights provide opportunities for visitors to try out the flying trapeze for a nominal fee. Their annual show, Circus Spectacular, includes performances from world-renowned jugglers, acrobats, tightrope walkers, hoopers, cabaret performers and aerialists. Circus Spectacular is organised every year during March at Latchis Theatre.

Shop at Brattleboro Farmer’s Market

The farmer’s market is open every summer from May to October. It is the best farmer’s market in entire southern Vermont. There are over 50 stalls selling home-grown farm fresh fruits and vegetables, dairy products, poultry, maple syrup, handicrafts, jewellery, scarves, desserts, and a diverse range of cuisines. The market is usually flocked by tourists and locals. It features live music and has a festive vibe. Experience the local culture and don’t forget to try Vermont’s famous maple syrup here.

Relish the Exciting Winter Carnival

The winter carnival takes place every year for 9 days in February in Brattleboro. This carnival has been a tradition of this town for close to 65 years. The various activities and events that are organised include cook-offs, musical concerts, dances, movie festival for kids, snowshoeing, skiing, snowmobile rides, sugar-on-snow, sleigh rides, scavenger hunts, cooking classes, bingo nights, puppet shows, ice fishing, and more. It is a fun-filled and entertaining event for both tourists and locals.

Check-out Vermont Artisan Designs

This is an art gallery exhibiting the premier quality works of Vermont’s artists and artisans. It is located in downtown Brattleboro and open daily from 12 pm to 4 pm. The gallery displays paintings, pottery, jewellery, sculptures, furniture, oil lamps, wine glasses, kaleidoscopes, fibre art, and more. It is one of the best galleries in the state of Vermont.

Dine by the Connecticut River

Whetstone Station is a waterfront diner located next to the Connecticut river in downtown Brattleboro. It is one of the most popular restaurants in this town and has both outdoor and indoor seating. It is well-known for its craft beer, splendid location, and rooftop biergarten. It offers phenomenal views through all four seasons. They have a fire-lit and cosy indoor dining facility for winters and visitors prefer dining outdoor against the picturesque backdrop in summers. The food here is also pretty awesome.

Participate in the Brattleboro Literary Festival

This is a 3-4 days festival that takes place annually in the initial weeks of October. The first literary fest was organised in the year 2002 and was inaugurated by Nobel Prize laureate Saul Bellow. The various events and workshops of the fest include poetry slams, meet your favourite author, debates, discussions, writing competitions, author’s book reading, short film screenings, and more. The Brattleboro literary festival has presented more than 400 award-winning authors. All events are completely free of charge for everyone.

Drop by Twice Upon A Time

Twice Upon A Time is a family-run antique store located in downtown Brattleboro. The store was founded in 1987 and is quite popular with tourists. They sell a wide array of vintage clothing, furniture, jewellery, sculptures, musical instruments, glassware, and home accessories. They’re open from Thursdays to Mondays from 12 pm to 5 pm.

Get Tickets to the Harris Hill Ski Jump Competition

This 90 metres Ski Jumping Competition is being organised in Brattleboro for close to a 100 years. It is one of the most popular winter events of this town. Renowned ski-jumpers from all over the globe flock to this countryside town every year in February for the 2 days tournament. The competition is currently being sponsored by Pepsi. This tournament is a must-visit if you’re traveling to Brattleboro in winter.

Stay @ The Inn on Putney Road Bed and Breakfast

This is one of the most tourist-loved accomodations in Brattleboro. Its building dates back to the early 1930s and was initially the private residence of a doctor working at  the Vermont Asylum and his family. The residence was converted into a bed and breakfast in 1992. The hotel is aesthetically pleasing and very clean. Its rooms offer breath-taking views of the mountains and gardens that surround it. The inn is located very close to downtown Brattleboro.


Wheel House Clay Centre is a business run by two regional artists of Brattleboro. They rent out pottery studios to professionals and also provide pottery lessons. It is a fun-filled therapeutic activity which also provides you with opportunities to meet new people while learning a new skill. This clay centre is a host to various events and parties.The works of the owners and the students are sold at this centre’s shop which is open for business daily from 12 pm to 6 pm.

Read a Book

Brattleboro has some really good book stores on Elliot Street, namely Everyone’s Book store and Brattleboro Book store. Both the shops have a wide range of books belonging to various categories. Spend a relaxing day reading a beautiful novel in your cosy hotel room or by the river here.

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Best Things to Do in Brattleboro, Vermont