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Vermont’s Best & Fun-est: Brattleboro’s Top Things To Do & Places To Visit

A visit to Brattleboro, Vermont pays off quickly. The charming town carries a little of everything, running from outdoor adventures through arts and culture to family fun. Local or visitor, there is always something in Brattleboro you had not noticed before.

Start with a stroll downtown, where unique shops, restaurants and galleries line the way. The architecture and the street art give you something to look at between doorways. For more adventure, the surrounding nature trails handle a hike or a bike ride. The possibilities in Brattleboro run further than the map suggests.

Historical sights through to local breweries, Brattleboro keeps you occupied. A unique experience or simply somewhere to sit and take in the scenery, the town covers both. Pack your bags and get ready for a trip to Brattleboro, Vermont.

Key Takeaways

• Brattleboro, Vermont offers a diverse range of activities for visitors and locals alike.
• Take a stroll downtown to explore the unique shops, restaurants, and galleries.
• From outdoor adventures to arts and culture to family fun, Brattleboro has something for everyone.

A Stroll Downtown

Brattleboro is small and unusually well stocked for its size. A town this size with a circus school, a sour brewery working foraged apples, an Art Deco cinema and a ski jump is not the normal arrangement. Downtown itself walks in well under an hour. The surprises are what keep people here longer than they had planned. Nothing here is oversold, which is a fair part of why it works.

Welcome to downtown Brattleboro. The historic downtown area is packed with quirky shops, good restaurants and plenty worth looking at. Let us take a stroll and see what the area holds.

Main Street Exploration

First stop, Main Street. This is the heart of downtown Brattleboro, where old and new buildings sit together and each one carries its own charm. Walk the length of it and take in the sights and sounds. A street performer or two turns up if the timing is right.

Shopping Extravaganza

Now to the shopping. Downtown Brattleboro is where a shopper wants to be, running from vintage clothing to handmade pottery. The Vermont Artisan Designs gallery is where the local artwork sits. And for new threads, the Vermont Country Store handles classic New England style.

Foodie Heaven

All that shopping can work up an appetite, so let’s talk about food. Downtown Brattleboro has no shortage of delicious eateries. For some classic pub fare, check out McNeill’s Brewery. If you’re in the mood for something a little fancier, try Peter Havens. And for all you vegans out there, don’t miss out on the amazing food at Superfresh. Organic Cafe.

That is the quick tour of downtown Brattleboro. Do not take our word for it, though. Get out there and see what turns up.

Outdoor Adventures

Ready for the great outdoors in Brattleboro, Vermont? Get your hiking boots on, pump the bike tires and grab a swimsuit, because the outdoor adventures here run in every direction.

Hiking Trails

Brattleboro is a hiker’s town through and through, with numerous trails opening onto the Green Mountains. For a challenging hike, Mount Wantastiquet climbs steeply to the summit and pays you back with long vistas over the Connecticut River Valley. For something more leisurely, the Retreat Trails carry a stone tower and a scenic path through the wilderness where deer and eagles turn up.

Biking Routes

Biking enthusiasts will find the cycling routes in Brattleboro worth the trip. The West River Trail is the popular choice, following the West River for 36 miles. For a harder ride, the Hogback Mountain Loop climbs a steep mountain road and gives you a thrilling descent through the fall foliage.

Swimming Spots

When the sun is out, cooling off in one of Brattleboro’s swimming spots is the obvious move. The Retreat Meadows draws swimmers and picnickers, with a large grassy area and a sandy beach. For something more secluded, Indian Pond sits tucked into the woods with crystal clear water for swimming and fishing.

Nature lover, adrenaline junkie or someone after a good summer day, Brattleboro covers it. Get out there and explore the great outdoors.

Historical Sights

Brattleboro, Vermont is a town steeped in history, and the historical sights are plentiful. Historic buildings through to covered bridges, there is a version here for you.

Historic Buildings

History buffs should not skip Brattleboro’s historic buildings. Many of them are listed on the National Register of Historic Places, which tells you they are worth the walk.

The Latchis Theatre is the notable one in Brattleboro. This Art Deco-style building went up in 1938 and has been entertaining audiences ever since. Today it holds four movie screens, a stage and a cafe.

The Brooks House is the other one to see. Built in 1871, it has been a fixture in downtown Brattleboro ever since. It now houses a variety of businesses, restaurants, shops and offices among them.

Covered Bridges

No trip to Vermont is complete without at least one covered bridge. Brattleboro has several to pick from.

The Creamery Covered Bridge is the iconic one in Brattleboro. Built in 1879, it is the only surviving example of a lattice truss covered bridge in the region. It photographs well at any time and better in the fall when the leaves are changing colors.

For a covered bridge well away from the crowds, head to the West Dummerston Covered Bridge. Built in 1872, it stands among the oldest covered bridges in Vermont. It sits in quiet, rural country and makes for a peaceful walk.

History buff or someone after a good sightseeing adventure, Brattleboro has the historical sights. Work through the historic buildings and the covered bridges, and bring a camera.

Arts and Culture

Brattleboro is a hub for arts and culture in Vermont. The arts scene here is thriving, and the museums, galleries and shows will keep you occupied for as long as you have.

Museums and Galleries

For museums, the Brattleboro Museum & Art Center belongs on the list. Founded in 1972, this contemporary art museum runs thought-provoking exhibits from a range of talented artists. Paintings and sculptures sit alongside installations and multimedia art.

For something a little more intimate, check out Gallery in the Woods. This cozy gallery shows work from local artists, and the artists themselves are often in the room and happy to talk. It is a good place to pick up an unusual souvenir or gift.

Concerts and Shows

On concerts and shows, Brattleboro covers a wide spread. The Stone Church is the popular venue, running everything from metal shows to folk music gatherings. It is where to catch live music and read the local scene properly.

For something a little more upscale, head to the Latchis Theatre. This historic theatre programs plays, musicals, concerts and comedy acts. The ornate decor and cozy atmosphere make it a strong choice for a night out.

Museums, galleries or live shows, Brattleboro has plenty. Grab your artsy friends and go and find the local scene.

The assumption is that a Vermont town means leaf season and very little else. Brattleboro runs harder than that. Summer puts kayaks on the Retreat Meadows and a jumping competition on Harris Hill, winter fills the Latchis with shows, and the breweries pour regardless of month. Fall is genuinely worth the drive up Hogback Mountain for the panorama. It is simply not the only reason to come to this town.

Family Fun

Brattleboro works well with your family in tow. There is a long list of fun things to do and places to visit that kids take to. These are the family-friendly activities here:

Farm Visits

Kids who love animals will do well on the farms around Brattleboro. Retreat Farm is where to start, with a petting zoo that puts them close to goats, sheep, pigs and more. A wagon ride runs around the farm alongside the history of the place. The farm store is worth a stop for fresh produce and homemade goodies.

Robb Family Farm is the other one to visit. This small family farm still produces maple syrup and runs plenty of fun activities for kids. They can watch the maple syrup being made, take a hayride and try milking a cow. A playground and picnic area mean you can make a day of it.

Playgrounds and Parks

Brattleboro has playgrounds and parks that hold children’s attention. Living Memorial Park is where to start, with a playground, a skate park and a pool. Trails run from it too, with good scenery along them.

West River Park is the other one worth the trip. A playground, a basketball court and a picnic area cover the basics, and the river is there for a swim on a hot day.

Whatever your kids are into, Brattleboro has a version of it. Pack up the car and come for a family vacation that fills itself.

Local Breweries

A visit to Brattleboro without the local craft beer misses the point. These are the breweries in town worth your time.

Craft Beer Tasting

First up is Hermit Thrush Brewery, known for their sour beers. The name suggests reclusive and the taproom is anything but, with a cozy room for working through their unique and flavorful brews. The beers use locally sourced ingredients and a wild yeast strain, which is where the distinct tartness comes from. Order the Brattlebeer, a sour beer made with foraged wild apples.

For a more traditional beer tasting experience, head over to McNeill’s Brewery. They have been brewing beer in Brattleboro since 1992 and have collected numerous awards for their craft beer. The taproom has a laid-back vibe and the classics to try are the Dead Horse IPA and the Pullman’s Porter.

Brewery Tours

To learn the brewing process properly, take a tour of Whetstone Station Brewery. Their knowledgeable staff walk you through the whole thing, grain to glass. You see the state-of-the-art brewing equipment and sample beers straight from the tank, and the brewery sits right on the river, so the view comes with the pint.

Brattleboro’s own McNeill’s Brewery is the other tour worth booking. They offer tours on Saturdays where the brewing process happens in front of you and the history of the brewery gets told. Samples of their award-winning beers come with it, which makes for a well-spent Saturday afternoon learning the craft beer industry in Vermont.

So, grab a pint and cheers to the local breweries in Brattleboro. With so many options to choose from, you’re sure to find a beer that suits your taste buds.

Seasonal Activities

Summer Fun

A Vermont summer is hard to beat, and Brattleboro makes good use of it. Take a dip in the refreshing waters of the West River at the town beach, or head to the Retreat Meadows for kayaking or canoeing. For the adventurous, paddleboarding and tubing down the river are both on.

For an adrenaline rush, the Harris Hill Ski Jump hosts a summer jumping competition. Brave athletes launch themselves off a 90-meter hill and travel through the air at speeds of up to 60 miles per hour. It is not a sight you soon forget.

Fall Foliage Views

Autumn in Vermont is something else, and Brattleboro sits well placed for the fall foliage. Take a scenic drive up to Hogback Mountain for panoramic views over the colorful hillsides. For something more active, the trails at Fort Dummer State Park run through the same forests on foot.

For the foliage from a different perspective, ride the Green Mountain Railroad’s Fall Foliage Train. It chugs through the countryside with the scenery on both sides and a delicious meal served on board.

However you take it in, the fall foliage in Brattleboro earns the trip. Bring a camera, because you will want every colorful moment of it.

Unique Experiences

For something different to do in Brattleboro, the unusual end is well covered. Here are two experiences that stay with you:

Circus Arts

You do not have to run away and join the circus to get the thrill of acrobatics and aerial arts. The New England Center for Circus Arts runs classes and workshops at every skill level, beginner through advanced. Juggling, stilt walking or swinging from a trapeze are all on the timetable. A talent for clowning around may turn up where you did not expect it.

Maple Syrup Tasting

Vermont is famous for its maple syrup and Brattleboro is no exception. Tour a local sugarhouse and watch maple sap boiled down into syrup. Then go further and try a maple syrup tasting, because like wine the syrup carries different flavor profiles depending on the tree, the time of year and the processing method. The range of tastes and textures surprises people. A new favorite pancake topping is a real possibility.

Why not mix things up and try something out of the ordinary? Circus enthusiast or maple syrup connoisseur, Brattleboro has the unusual experiences to offer.

Frequently Asked Questions

What are some free things to do in Brattleboro that won’t break the bank?

Brattleboro carries plenty of free activities that cost nothing at all. Take a stroll through the Brattleboro Farmers’ Market for fresh produce, baked goods and crafts. Walk the Retreat Trails, which run scenic paths through wilderness where deer and eagles live. For the adventurous, hike to the top of the Harris Hill Ski Jump and take in the surrounding mountains.

Are there any fun activities for kids in Brattleboro?

There are plenty of fun activities for kids in Brattleboro. Take them to the Brattleboro Museum & Arts Center to work through thought-provoking exhibits from a range of talented artists. The Robb Family Farm puts them alongside farm animals. For the outdoors, Living Memorial Park has a playground, a swimming pool and a skating rink.

Where can I find the best shopping in Brattleboro?

For unique and one-of-a-kind items, head to the downtown area of Brattleboro. Boutique shops and art galleries there carry handmade jewelry, pottery and other crafts. The Brattleboro Outlet Center is the other option, with stores covering clothing, electronics and home goods.

What are some must-try restaurants in Brattleboro?

Brattleboro runs a diverse culinary scene with plenty to choose between. For breakfast, the Chelsea Royal Diner does classic American diner fare with a modern twist. For Italian, T.J. Buckleys handles pasta dishes and wood-fired pizzas. For a unique dining experience, Duo Restaurant runs a farm-to-table menu built on locally sourced ingredients.

What are some nearby day trips from Brattleboro that are worth the drive?

There are plenty of nearby day trips from Brattleboro worth the drive. Head to the charming town of Wilmington, known for its historic covered bridges and scenic hiking trails. The Green Mountain National Forest is the other option, covering hiking, camping and fishing.

Is the Creamery Covered Bridge really made of cream? (Asking for a friend)

We hate to break it to you, but the Creamery Covered Bridge is not actually made of cream. It takes its name from the nearby Creamery Covered Bridge Farm, which used to produce cream. The bridge itself is made of wood and was built in 1879.

Frequently asked questions about Brattleboro, Vermont

How old is the Creamery Covered Bridge?

Built in 1879. It is the only surviving lattice truss covered bridge left in the region, which is the reason people photograph it rather than simply drive across it. The West Dummerston Covered Bridge is older still, dating right back to 1872. That one sits out in quiet rural country and sees far fewer visitors. Vermont has kept these things standing for well over a century without making much noise about it.

Which Brattleboro brewery should you start with?

Hermit Thrush, for the sheer oddity. The brewery works with a wild yeast strain and locally sourced ingredients, which gives the beer a tartness you will not find in a standard taproom. Brattlebeer uses foraged wild apples and is the one to order first. McNeill’s has been brewing here since 1992 and covers the traditional end of things. Whetstone Station runs the brewery tours and sits directly on the river itself.

What does the Brattleboro Museum & Art Center show?

Contemporary work, since 1972. The Brattleboro Museum & Art Center has run thought-provoking exhibits from a range of talented artists for decades now, which is a long stretch for a town of this size. Paintings and sculpture sit beside installations and multimedia work of every sort. Gallery in the Woods handles the local end of it far more intimately. Between the two of them you get the whole arc of what this town makes.

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