20 Things To Do In Brattleboro

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Nestled in the picturesque landscapes of southern Vermont, near Green Mountain National Forest, Brattleboro is a delightful gem of a quintessential New England town. With a vibrant community spirit and rich cultural heritage, the town is a charming place to visit for any length of time. Brattleboro is ideal for outdoorsy types as its surrounded by the lush forests and rolling hills of the surrounding national preserves, there are tons of hiking and biking trails to explore. The town’s many rivers and lakes are popular with kayakers and anglers.

During the colder months, the snow turns the undulating landscape into a winter wonderland of ski runs and snowshoe routes for you to challenge yourself on. If you prefer sheltering from the elements and enjoying indoors entertainment, then the Brattleboro arts and culture scene will be sure to keep you busy. There are plenty of museums, galleries, and historic landmarks to fill up your itinerary and keep you occupied. This article is your gateway to appreciating the myriad of activities awaiting you in Brattleboro. We’ll go through the best things to do in Brattleboro, Vermont, so you’ll know exactly how to spend your time in this idyllic New England community.

Brattleboro, Vermont

brattleboro vermont over the river
Looking for things to do in Brattleboro? Check out our top 20 list.

20 Best Things To Do In Brattleboro, Vermont

1- Browse Brattleboro Museum & Art Center

Start your visit with a trip to the Brattleboro Museum and Art Centre to get an introduction to the town’s creative scene.

Housed within an old railway station, the museum hosts a range of exhibitions celebrating contemporary works across a range of mediums and topics.

With a huge diversity on work on show, there’s certain to be something to capture your imagination.

Along with the galleries, the Art Centre also has a full calendar of events, workshops, and educational programmes to get visitors and the local community more in touch with their own creativity.


Head over to 10 Vernon St, Brattleboro, VT 05301, United States.

2- Look Around The Brattleboro Historical Society

If you’re interested in the history of the area, pay a visit to the Brattleboro Historical Society.

The dedicated society members have curated exhibits on notable people, places, and events from the local area, so you can dive right into learning about Brattleboro’s heritage, development, and culture.

The hours the museum is open are limited, though. It’s only open on Thursdays between 1 and 4pm and Saturdays from 10am to 12pm, so make sure to plan your visit carefully.

Go to 230 Main St, Brattleboro, VT 05301, United States. Join this Guided Brattleboro History Walking Tour to learn more.

3- Visit Retreat Farm

To really get in touch with the local community and culture, pay a visit to Retreat Farm.

The working farm has tons for visitors to get involved in, from sampling local produce to meeting the animal residents.

Walking trails wind through the surrounding forest, making it a great place to simply enjoy nature.

There is even a storybook walk, where kids can follow a trail through the trees to find the next part of a story, so it’s perfect for a family day out.

Find It At 45 Farmhouse Sq, Brattleboro, VT 05301, United States.

4- Cross Creamery Covered Bridge

covered bridge over a river
Exploring historic covered bridges is one of the things to do around Brattleboro. Pictured here is the longest covered bridge in Vermont.

The charming, covered bridges are an iconic symbol of Vermont, and you’ll find several beautiful examples of them in the area around Brattleboro.

Creamery Covered Bridge is just off the main road leading west out of town.

Built back in 1879, the bridge is in excellent condition, appearing almost exactly as it would have done when it was first installed.

Now only open to pedestrians, Creamery Covered Bridge makes an excellent goal point for a scenic walk around the city limits.

Head along to 500 Western Ave, Brattleboro, VT 05301, United States.

5- Admire Retreat Tower

Atop a leafy hill overlooking the town, you’ll find Retreat Tower poking out of the trees.

The stone tower dates back to the late 1800s and was built by residents of the local asylum.

It’s history, along with its lonely location and moss-covered façade, lend it a curiously eerie quality.

In fact, there are many paranormal legends and sightings linked to it.

Find it at Retreat Tower, Reservoir Loop, Brattleboro, VT 05301, United States.

6- See What’s On At The Stone Church

The Stone Church is one of Brattleboro’s principle music venues, hosting a huge range of acts and performances.

The venue is, indeed, housed within a beautiful, historic church, with most of the original details and features still intact, creating a delightfully quirky location for a concert.

If you have a love for live music, you will definitely want to see what’s on here during your stay, so you can enjoy an unforgettable night out at a truly unique place.

Go to 210 Main St, Brattleboro, VT 05301, United States.

7- See The Exhibits Of Estey Organ Museum

If you’re interested in the history of music in the area, you should definitely pop into the Estey Organ Museum.

Dedicated to the history of the Estey Organ Company, which was founded in Brattleboro, the museum is home to a collection of pipe, reed, and electronic organs, as well as related artefacts.

The entry fee is $5 for non-members, and visiting hours are limited to between 2 and 4pm on Saturdays, from May through October, so make sure to schedule your visit in your itinerary.

Find it at 108 Birge St, Brattleboro, VT 05301, United States.

8- Catch A Show At Brattleboro Music Center

Enjoy the local musical by attending a concert at the Brattleboro Music Centre.

The main music school in town, Brattleboro Music Centre puts on a packed calendar of events and festivals through the year to showcase the talents of their students.

The BMC boasts six performance groups, as well as being open to visiting artists, so there’s a fantastic range of styles for you to enjoy.

Head over to 72 Blanche Moyse Wy, Brattleboro, VT 05301, United States.

9- Look For The Fort Dummer Monument

At the base of Cotton Mill Hill, heading south out of the town, is the Fort Dummer Monument.

Tucked away beside of the road, the granite monument marks the spot where the eponymous British fort was built in the early 1700s when the town was founded.

While small, it is a charming nod to the origins and heritage of Brattleboro, and well worth stopping by for a moment if you’re in the area.

Look around Brattleboro, VT 05301, United States.

10- Relax On Brattleboro Common

When you need a comfortable spot to relax in the open air, head over to Brattleboro Common.

The leafy, green space has plenty of benches to rest on, or lay back on the lush lawns and while away the afternoon.

Events are often held in the common, based around the central gazebo, so it’s worth seeing if there are any markets or festivals occurring during your stay.

Go to Park Pl, Brattleboro, VT 05301, United States.

11- Sample Local Produce At Brattleboro Summer Farmer’s Market

Throughout the summer, from May to October, you can head over to Brattleboro Farmer’s Market on a Saturday morning to pick up some fantastically fresh local produce and mingle with the community.

Just the other side of Creamery Covered Bridge, it makes a great destination for a Saturday morning walk, but there is also plenty of parking if you’d rather just drive.

Find it at 570 Western Ave, West Brattleboro, VT 05301, United States.

12- Take Your Shot At Living Memorial Park Disc Golf Course

Cross the Creamery Covered Bridge and you’ll find yourself at Living Memorial Park, where you can either just kick back and relax in the wide-open field, or you can try your hand at a round of disc golf.

The course is well-maintained and perfect for beginner and seasoned pros alike.

Head along to 158 Memorial Park Dr, West Brattleboro, VT 05301, United States.

13- Slide Down Brattleboro Ski Hill

When winter hits and Vermont is covered in a blanket of snow, Living Memorial Park is turned into the local ski track.

Complete with a volunteer operated ski-lift, the gentle slope is ideal for beginners.

It’s especially popular with families, who head up the slope to ski, snowboard, or sled back down.

Go to Memorial Park Dr, West Brattleboro, VT 05301, United States.

14- Explore Madame Sherri Forest

Fall colours around Indian Pond.
One of the outdoorsy things to do in Brattleboro va is to visit Indian Pond in Madame Sherri Forest.

Brattleboro is surrounded by stunning natural landscapes, but if you really want to escape into the wilderness, you just need to hop across the Connecticut River into New Hampshire and explore the trails of Madame Sherri Forest.

The lush forest is riddled with hiking routes, many of which lead to ledges and ridges that offer stunning views across the mountains and back across to Brattleboro.

Head into West Chesterfield, NH 03466, United States.

15- Pay A Visit To Harris Hill Ski Jump

If you’re visiting in winter, you’ll want to check when the annual Harris Hill Ski Jump is taking place.

Every year, expert skiers flock to the area to battle it out in a competition that’s been running for over a century.

The impressive ski jump has even been used in Olympic events, so you know the standards of entry will be high.

Go to Cedar St, Brattleboro, VT 05301, United States.

16- Get A Taste For The Town At Grafton Village Cheese Company

knife cutting into cheese
Visiting a cheese farm is one of the fun things to do around Brattleboro.

Sample some local flavour and pick up some quirky souvenirs with a visit to the Grafton Village Cheese Company.

Located on Retreat Farm, Grafton Village uses carefully selected local ingredients and traditional techniques to create small batch cheeses in a variety of styles and flavours.

Whether you just like a good, solid cheddar, or feel like branching out into sweet maple or spicy chilli flavours, there’s plenty for you to try.

You can even see if cave aged cheese really has a noticeable difference to the more typical aging style.

Head into n400 Linden St, Brattleboro, VT 05301, United States.

17- Strike Out For Old Jelly Mill Falls

The land and forests around Brattleboro are packed with natural attractions for you to track down.

One that’s well worth seeking out is the Old Jelly Mill waterfall, just off the main road, a few miles north of Brattleboro.

You can either enjoy a relaxing hike through the woods or hop in your car and follow the West River.

The falls are low and shallow, so you needn’t worry about getting swept away.

It’s beautiful in any season, running at full tilt in the spring and slowing to a trickle when the river freezes over in winter.

Head for Dummerston, VT 05301, United States.

18- Visit Scott Farm Orchard

Another great spot to get your hands on some super fresh, local produce is Scott Farm Orchard.

Best known for its heirloom apples, the orchard also grows a range of other fruits including pears, quince, peaches, and persimmons, with the produce the orchard grows varying by season.

You can check their website to see what will be fresh and ready during your visit.

They also often run pick-your-own schemes, so you can get involved in picking the produce yourself.

Or let them do the work and just pop along to one of the many events and workshops they hold throughout the year.

Go to 707 Kipling Rd, Dummerston, VT 05301, United States.

19- Make Merry At Santa’s Land USA

If you thought this winter wonderland couldn’t get more festive during the holiday season, think again.

Just a few miles north of Brattleboro, you can find Santa’s Land USA just off Interstate 91.

Packed with fully themed rides, attractions, and games, it’s a fantastic family day out to get everyone in the Christmas mood.

The seasonal theme park is open on weekends from early October through to Christmas eve, so there’s plenty of time to get in the festive spirit.

Go to 655 Bellows Falls Rd, Putney, VT 05346, United States.

20- Cross The Boston & Maine Railroad Fort Hill Bridge

Crossing the river at the south end of town is the historic Boston and Maine Railroad Fort Hill Bridge.

Once a key track for freight trains running to and from Canada, the bridge has been out of use for decades.

Even so, the charming iron truss bridge remains as a shortcut for daring pedestrians crossing over to New Hampshire or as a must visit attraction for fans of rail history or urban decay.

Head over to Riverside Dr, Hinsdale, NH 03451, United States.

orange and yellow fall colours
Seeing the fall colours is one of the top things to do in Brattleboro.

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Steve Burden
Steve Burden is an avid traveller and experienced writer. As a former pro wrestler, Steve used to travel frequently for work throughout the USA and Europe. Having spent the last decade travelling all over the world in search of new sights and experiences, he has turned his love for travel into a new career helping others decide on the best places to visit, as well as what to see when they get there.