20 Best Things to Do in Brattleboro, VT

Brattleboro, VT
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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 throughout the year.

It town provides endless opportunities for a wide array of outdoor activities like hiking, camping, paddle boarding, fishing, canoeing, swimming, skiing, and snowboarding.

The museums, galleries, festivals, and events at Brattleboro celebrate this vibrant town's local culture.

To make the most out of your visit, here's a list of the best things to do in Brattleboro, Vermont:

Experience Farm Life at Retreat Farm

View of Brattleboro farm
Cavan-Images / shutterstock.com

Spend a day at Retreat Farm to experience the rural way of life.

Visitors can play with the farm animals or watch the fruits, vegetables, and flowers grow.

The farm is home to piglets, cows, goats, ewes, lambs, bucks, sheep, donkeys, and oxen.

Retreat Farm is a perfect spot for a nice picnic.

It's also connected to a forest with several splendid hiking trails.

Admire Nature Views along the West River Trail

Scenic view of  Brattleboro forest
Cavan-Images / shutterstock.com

The Retreat Farm is connected to a trail-traversed forest.

It is a 9-mile network of invigorating hiking trails covering over 600 acres of farm fields and forestlands.

This is one of the top tourist attractions in Brattleboro.

The trails are pretty easy and offer phenomenal views of the town's dense greenery.

The views are equally breathtaking in every season.

The West River Trail is a 36-mile hiking trail parallel to the serene West River.

It has astounding views throughout the year.

You should also check out the Mount Wantastiquet Trail, a 4-mile 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 panoramic views of the Connecticut River Valley, Brattleboro, and distant mountains.

This hike is slightly tricky, but the mind-blowing views are worth it.

Watch a Show at Latchis Theatre

Front view of Latchis Theatre
Beyond My Ken / CC BY-SA

Latchis is a historic theater with ornate Greco Deco architecture, located in downtown Brattleboro.

This theater is a prominent part of this town’s local culture and has been organizing live performances and playing cinema for over 80 years.

It is hosts the town’s renowned film festival, which takes place every year around October or November.

The festival features a broad array of documentaries, short films, and movies from all over the world.

Latchis Theatre is a part of the famous Latchis Hotel.

Travel Back in Time at Estey Organ Museum

Exterior of the Estey Organ company buildings
Qrpnut, CC BY-SA 3.0, via Wikimedia Commons

The Estey Organ Company was one of the top organ manufacturing companies in the world between the late 1800s to 1950s.

It sold premier quality reed, pipe, and electronic organs to various countries across six continents.

Jacob Estey founded the company in Brattleboro during the 1850s.

Exterior of the Estey Organ Company buildings
Qrpnut, CC BY-SA 3.0, via Wikimedia Commons

The museum exhibits several collections of the Estey Company’s manufactured organs.

Images of the company’s factory buildings, employees, catalogs, and business cards are 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.

A pump organ instrument made by Estey Organ Company
Doug Miller, CC BY 2.0, via Wikimedia Commons

Enjoy Refreshing Summer Activities like Swimming and Kayaking

Scenic view of  Connecticut River Brattleboro
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Swimming, kayaking, canoeing, fishing, paddle boarding, and tubing are popular recreational water sports in Brattleboro in the summer.

The Connecticut and West rivers provide excellent opportunities for water-based activities in this region.

The rivers are crystalline and have gorgeous scenic views.

View of the gentle Connecticut River flowing with raws of trees on both the sides
Christian Hinkle / Shutterstock.com

There are various businesses around the town providing the requisite rental watercraft and protective gear.

Enjoy a perfect summer day engaging in such recreational activities followed by a fun picnic.

Stream flowing below the longest covered wooden bridge in Vermont
travelview / Shutterstock.com

Attend the Annual Strolling of the Heifers Parade

Every year, crowds gather to attend Brattleboro's world-renowned parade and cow festival.

It is a pre-summer tradition organized every June with a new and unique theme.

The parade features numerous heifers strolling down the town's streets with the farmers.

It is a vibrant and colorful festival that includes live music, performances, farmer's breakfasts, 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 homegrown products, innovation in agriculture, and sustainable living.

It lets you catch a glimpse of the local culture of Brattleboro.

Explore Art at Brattleboro Museum & Art Center

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

The Brattleboro Museum and Art Center was once a historic railway station.

It showcases contemporary artworks by regional artists.

This center dates back to 1972 and is one of the town's tourist hotspots.

Being a non-collecting museum, it rotates its exhibitions quarterly.

The principal objectives of this art center and museum are to support and nurture the local art talent and create awareness of the town’s rich cultural history.

The museum has six galleries and holds around 20 exhibitions annually.

Visit this gallery and explore the captivating works of art.

Enjoy Winter Activities Like Skiing and Snowboarding

Scenic view of Brattleboro Snow
Felix Lipov / shutterstock.com

Enjoy the mesmerizing views of the snow-covered town in the winter.

Indulge in skiing, snowboarding, ice skating, cross-country skiing, and snowshoeing.

People ski jumping at brattleboro during winter
redjar, CC BY-SA 2.0, via Wikimedia Commons

Winters in Brattleboro are enjoyable.

Rental snowshoes, 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 at NECCA

New England Center for Circus Arts or NECCA is a well-known circus school  in Brattleboro.

It hosts many shows, events, and workshops all year round.

Their monthly show called Beta Nights features performances by the students and other residents of the town.

One of their monthly programs, Flight Nights, lets visitors try out the flying trapeze for a nominal fee.

They also hold an annual show called Circus Spectacular, including performances from world-renowned jugglers, acrobats, tightrope walkers, hoopers, cabaret performers, and aerialists.

Circus Spectacular is organized every March at Latchis Theatre.

Shop at Brattleboro Farmers' Market

The farmers' market is open every summer from May to October.

It is the best farmers' market in entire southern Vermont.

There are over 50 stalls selling homegrown farm-fresh fruits and vegetables, dairy products, poultry, maple syrup, handicrafts, jewelry, scarves, desserts, and a diverse range of cuisines.

Don’t forget to try Vermont’s famous maple syrup here!

The market is usually flocked by tourists and locals.

In addition to fresh goods, the market also features live music and has a festive vibe.

Relish Brattleboro's Exciting Winter Carnival

The winter carnival takes place every year for nine days in February.

This carnival has been a town tradition for close to 65 years.

The activities include cook-offs, musical concerts, dances, movie festivals for kids, snowshoeing, skiing, snowmobile rides, sugar-on-snow, sleigh rides, scavenger hunts, cooking classes, bingo nights, puppet shows, and ice fishing.

The Brattleboro Winter Carnival is a fun-filled and entertaining event for tourists and locals.

Check Out Vermont Artisan Designs

Vermont Artisan Designs is an art gallery exhibiting the premier quality works of the state's artists and artisans.

You can find it in downtown Brattleboro.

The gallery displays paintings, pottery, jewelry, sculptures, furniture, oil lamps, wine glasses, kaleidoscopes, fiber art, and more.

It is one of the best galleries in the state of Vermont.

Dine by the Connecticut River

Scenic view of Connecticut River and a bridge over it
Jon Bilous / Shutterstock.com

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 outdoor and indoor seating.

It is well-known for its craft beer, splendid location, and rooftop beer garden.

It offers phenomenal views through all four seasons.

They have fire-lit and cozy indoor dining facilities for the winter, while visitors prefer dining outdoor against the picturesque backdrop in the summer.

Participate in the Brattleboro Literary Festival

This is a three-to-four-day festival that takes place every October.

The first literary fest was organized in the year 2002 and was inaugurated by Nobel Prize laureate Saul Bellow.

The festival features various events and workshops like poetry slams, debates, discussions, writing competitions, author’s book readings, short film screenings, and more.

You might even get the chance to meet your favorite author.

The Brattleboro Literary Festival has presented more than 400 award-winning authors.

All events are entirely free of charge.

Shop for Antiques at 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, jewelry, sculptures, musical instruments, glassware, and home accessories.

Get Tickets to the Harris Hill Ski Jump Competition

The obstacle for Harris Hill Ski Jump Competition
Brandt Kurowski from Brattleboro, VT, USA, CC BY 2.0, via Wikimedia Commons

This 90-meter Ski Jumping Competition has been organized in Brattleboro for nearly a hundred years.

It is one of the town's most popular events.

A participant at Harris Hill Ski Jump Competition
Brandt Kurowski from Brattleboro, VT, USA, CC BY 2.0, via Wikimedia Commons

Ski-jumpers from all over the globe flock to this countryside town every February for the two-day tournament.

Attending this tournament is a must if you’re traveling to Brattleboro in the winter.

People watching the Harris Hill Ski Jump Competition
Jared and Corin, CC BY-SA 2.0, via Wikimedia Commons

Stay at The Inn on Putney Road Bed and Breakfast

This is one of the most tourist-loved accommodations 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 bed and breakfast in 1992.

Its rooms offer breathtaking views of the mountains and gardens that surround it.

The inn is located very close to downtown Brattleboro.

Take a Pottery Class at Wheelhouse Clay Center

Wheelhouse 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's a fun-filled therapeutic activity that provides you with opportunities to meet new people while learning a new skill.

This clay center hosts various events and parties.

The works of the owners and the students are sold at this center’s shop as well.

Explore Brattleboro's Book Shops

Brattleboro has some excellent book stores on Elliot Street, namely Everyone’s Books and Brattleboro Books.

Both the shops have a wide range of books belonging to various categories.

Spend a relaxing day reading a beautiful novel in your cozy hotel room or by the river here.

Take a Selfie with the Creamery Covered Bridge

Beautiful red Creamery Covered Bridge during fall
Structured Vision / Shutterstock.com

Creamery Covered Bridge has provided Vermont with a unique historic and tourist attraction.

The bridge crosses Whetstone Brook and is closed to vehicle traffic nowadays.

The Creamery Covered Bridge was constructed in 1879 and has been structurally reinforced in recent years, allowing it to carry on for many more years as this hidden historical gem for locals.

Side view of the Creamery Covered Bridge with a stream flowing beneath it
littlenySTOCK / Shutterstock.com

It is regarded as the last covered bridge from an original nine in the 19th century.

The Creamery Covered Bridge is an 80-foot (24 m) long and 19-foot (5.8 m) wide bridge that rests on stone abutments.

It's no secret that the Creamery Covered Bridge is a prized local treasure.

Grab Fresh Produce at the Brattleboro Area Farmers' Market

Situated in 570 Western Avenue (Route 9), Brattleboro, Vermont, the Brattleboro Area Farmers' Market is a great place to visit on market days.

The market is a gathering of all the main farmers around Southern Vermont.

However, it also gives local residents and tourists an experience with what Vermont food products are all about.

The market features fresh fruits and vegetables, homemade goods, and lots of terrific food trucks with culinary creations from around the globe.

There are free-range beef and lamb products, cheeses, freshly baked pastries, maple syrup, and honey on display.

There is also a weekly 0pen mic night right in the center of the market, where musicians perform traditional music and original songs.

The Brattleboro Area Farmers' Market takes place between May and October and runs from 9:00 a.m. until 2:00 p.m. every Saturday.

Uncover the Rich History at the Brattleboro History Center Museum

The Brattleboro Historical Society is home to some intriguing equipment, historical artifacts, records, and documents.

Since its inception in 1982, Brattleboro Historical Society has been so diligent about taking care of the society’s collections and sharing them with the public.

The center aims to help people learn all sorts of new facts relating to Brattleboro's past.

The Brattleboro History Center Museum gives local residents and businesses the opportunity to explore the history of their community.

It fosters the creative energy downtown by collaborating with groups during their exhibitions and events.

The center's gift shop has Brattleboro-related postcards, books, photos, posters, maps, and tag sale items available.

Other Things to Do Nearby

Take a Trip to Naulakha

Exterior of Naulakha
Daderot, CC0, via Wikimedia Commons

Naulakha is a historical landmark that was once the home of world-famous English novelist and Nobel Prize laureate Rudyard Kipling.

This house dates back to the late 1800s and still retains most of the author's original furniture.

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.

Exterior of Naulakha
Lou Sander, CC BY-SA 4.0, via Wikimedia Commons

"Naulakha" means 900,000 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.

Final Thoughts

You're in for an exciting time at this charming town that offers countless activities for visitors to enjoy.

Tourists will surely have a delightful time exploring its nature trails, visiting its museums, and taking part in the town's thrilling festivities.

Keep this list of things to do in Brattleboro for when you get the chance to visit!

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Best Things to Do in Brattleboro, Vermont