16 Top-Rated Things to Do in Brattleboro, VT

Barbara Radcliffe Rogers and her husband, photographer Stillman Rogers, live a few miles from Brattleboro and do most of their shopping there. They especially enjoy Brattleboro's bookstores and art galleries.

The best thing about Brattleboro is just being there. There's a relaxed, easygoing vibe that's both artsy and outdoorsy (Main Street shops testify to both these). A turn up Elliot Street will assure you that bookish is another accurate description.

What you won't find is pretense. Flannel shirts, down jackets, hiking boots, and Birkenstocks are fashion statements here, and the best things to do in Brattleboro are to follow the locals to their favorite places: art galleries, kayaking waters, hiking and cycling trails, and one of New England's best farmers markets.

This southern Vermont town was home to the back-to-the-landers who settled here in the 1960s and '70s. Many of them stayed, and their lifestyle and progressive attitudes still show in the do-it-yourself and buy-local civic mind-set.

Tourists will find iconic Vermont attractions, too, including two covered bridges, pick-your-own apple orchards, and a premier display of stone walls. And there are one-of-a-kind things to do that you'll find only here: You can warm your hands around a cup of hot cocoa as you watch world champion ski jumpers fly through the frosty air, or perhaps you'd like to walk inside a pipe organ to see how it works.

Whatever your pleasures, you'll find plenty of places to visit with this handy list of the best things to do in Brattleboro, Vermont.

1. Main Street

If you were to draw a picture of classic 19^th-century small town Main Street, it would look a lot like Brattleboro. Three blocks of brick mercantile buildings face each other across Vermont Route 5 as it passes through the center of town. Take time to look up and admire the decorative brickwork and notice the absence of box and chain stores.

The Main Street shops tell you a lot about Brattleboro. Within its three blocks, you'll find two bicycle stores (one of which is also a sporting goods store with snowshoes, skate-, and snowboards), Beadniks, with the largest selection of beads in New England, and a museum of antique beads downstairs.

At Sam's, a Vermont institution since the 1930s, you can shop for outdoor and practical clothing. Step inside, and you'll see that it goes on through room after room on three floors and into an adjoining building. Like Sam's, Brown and Robert Hardware seems to go on forever, with the region's best housewares center tucked into one side; you can find everything here, from cast iron skillets to Cuisinarts.

Main Street is a place to stroll, browse, shop, say hello to strangers, and stop for a bite. Stray up Elliot and Flat Streets and continue down the hill past the elegant Art Deco Latchis Hotel and Theater to find the Brattleboro Co-op and its selection of Vermont cheeses.

Get your Birkenstocks at The Shoe Tree, a flannel shirt at Sam's, grab a coffee at Mocha Joe's, or a pastry from Amy's Bakery, and you're ready to amble along Main Street.

2. Take a Gallery Walk

As you walk down Main Street and adjoining Elliot Street, you're sure to notice the number of art galleries and shops featuring handcrafted works. On the first Friday evening of each month, more than a dozen of these stay open for a Gallery Walk from 5 until 8 or 9pm. You can visit on your own with the help of a gallery map or join a free docent-led tour.

Of course, you can visit the art galleries during business hours most days, as well, to find fine art, photography, and hand-crafted jewelry, clothing, pottery, furniture, and decorative objects.

On Main Street are Mitchel Gibbons Fine Art, Penelope Wurr, Gallery in Woods, Vermont Artisan Designs, and ZPOTS. The latter is a family-owned studio of paintings and pottery that includes tableware and decorative works.

In the autumn, look for the collection of terra-cotta jack-o-lanterns; each one is unique, and you can choose from dozens of original faces.

Official site: https://www.brattleboro.com/downtown/gallery-walk/

3. Shop and Eat Lunch at the Brattleboro Farmers' Market

In what is considered the premier farmers market in the northeast, and a popular attraction for tourists, as many as 50 vendors display their produce and handwork in a tree-shaded spot beside Whetstone Brook. In the center are picnic tables (an entire row of vendors sell ready-to-eat foods), a big sandbox full of kids, and very often a group of local musicians playing anything from Celtic jigs to bluegrass and jazz.

While the purpose was — and is — to sell vegetables, fruits, herbs, flowers, plants, maple syrup, honey, cheese, and other products of local farms, the market has grown into a weekly social gathering place and market for hand-crafted works. You'll find pottery, hand-spun and woven woolens, silver jewelry, fresh-baked breads, jars of farm-made preserves, handmade soaps, granola, and inlaid wood breadboards.

The market is a popular place to visit for Saturday lunch, with a choice of foods from around the world. Along with Thai favorites, you might find French crepes, Indian vegetarian dishes, French macarons, stuffed grape leaves, kimchi and dumplings, baguettes, gelato, and fresh-squeezed lemonade.

Address: 570 Western Ave. (Route 9), West Brattleboro, Vermont

Official site: www.brattleborofarmersmarket.com

4. Visit the Brattleboro Museum & Art Center

You'll find more works by local artists at Brattleboro Museum & Art Center, located inside the distinctive former Central Vermont & Boston & Maine Union Station building at the foot of Main Street. The non-collecting museum is dedicated to presenting rotating exhibits that not only expose the work of contemporary local artists, but provoke thought and inspire creativity.

Past exhibitions have included subjects as diverse as works representing art used for social change and the entries in an annual LEGO contest. More than 60 programs each year include classes and workshops on subjects such as wool felting, sculpture with foraged materials, transfer prints, oral history, Ukrainian Easter Eggs, and mask making.

Address: 10 Vernon Street, Brattleboro, Vermont

Official site: www.brattleboromuseum.org

5. Take in a Show at the Latchis Theater

You can't miss the marquee of the Latchis Theater, nor the Art Deco Latchis Hotel above it. The Latchis is actually four movie theaters, three of them also used as performance spaces, so you might also find a Gilbert and Sullivan operetta or a concert by the Windham Philharmonic.

The beautifully restored main theater, which seats 750, has the largest screen in southern Vermont and all the theaters are fully accessible. In addition, audio amplification headphones, closed captioning goggles, and descriptive audio technology headphones are available free of charge.

Address: 50 Main Street, Brattleboro, Vermont

Official site: https://latchis.com

6. Go Retro Shopping

The combined legacy of the back-to-the-landers and good old Yankee thrift has made Brattleboro the goal of shoppers looking for all things vintage, retro, repurposed, and second-hand. Whether it's '70s or '80s fashions or good solid furniture for an apartment, Brattleboro is the place to look.

For clothing, begin at Boomerang on Main Street, where you'll find a blend of used, vintage, and new wearables for both men and women. Mixed in with gently worn sportswear and current styles, you may find a fringed suede cowboy shirt or a Fedora hat.

Look here, too, for costume jewelry, but for the real thing, step a few doors up Main Street to Renaissance. One of New England's best collections of antique and estate jewelry may include treasures such as an Italian cameo ring, old mine cut diamonds, or a Victorian mourning pin.

Persephanie, almost hidden in a sunken doorway opposite the Latchis Theater, features an eclectic mix of vintage, upcycled, and handcrafted finds displayed with an eye for home décor.

Just off Main on Flat Street, Experienced Goods is a charity thrift shop funding the Brattleboro Area Hospice. This isn't a jumble sale; everything is clean and undamaged.

Back on Main Street, Turn it Up! Is the place to look for vintage vinyl records from the 1950s, VHS recordings, CDs, posters, and vintage memorabilia.

The largest shop, Twice Upon a Time, fills three floors of a former department store opposite Sam's, and once inside this Aladdin's cave, you'll have trouble leaving. Whether you're looking to outfit your kitchen with vintage 1940s painted-handle tools, or furnish a room in mid-century modern, you'll likely find what you want here. It's like browsing through a museum of the past century or two.

7. Walk the Retreat Trails

Within walking distance of Main Street is a network of 10 miles of walking trails across a wooded hillside that were built by and for the patients at the Brattleboro Retreat, a private mental health and addictions center.

You can access these from the Retreat Farm or from behind the solar field on Western Avenue, and you can plan a hike of any length or terrain by combining several loops.

For a steep climb, choose the trail up to the Retreat Tower, built by staff and patients in the 1800s. Other trails pass the Harris Hill Ski Jump and an Ice Pond that provided more than 30,000 ice blocks a year for the Retreat. Near the Western Avenue entrance is the one-mile Woodlands Interpretive Trail, with sign boards describing interesting natural features.

These trails are among the best hikes in Vermont.

Address: Off Western Avenue (Route 9), Brattleboro, Vermont

8. Get Lost in Bookstores

Considering that Rudyard Kipling wrote some of his best-loved works here, Saul Bellow lived here for a quarter century, and the police force was made world-famous by Archer Mayer, it's not surprising that Brattleboro is a bookish kind of place. You'll find their works and thousands more, new and used, in Brattleboro's busy bookshops.

Two of them face each other across Elliot Street, one for new books, one for used. Everyone's Books is devoted to new books in all genres and subjects, but especially strong in the environment, social action, politics, nature, food, history, and do-it-yourself. The selection of children's literature is especially good.

Brattleboro Books, across the street, is floor-to-ceiling in used books. From vintage Julia Child to the latest bestsellers that have been read once, you'll find it here. Bibliophiles and avid readers won't want to leave. The same is true of the smaller Book Lovers on Flat Street, where you'll find used books, especially strong in niche subjects that are hard to find elsewhere.

9. Photograph Covered Bridges

Covered Bridge fans will find two, one in Brattleboro and one just over the line into neighboring Dummerston.

Visible from Western Avenue (Route 9) just before the Brattleboro Farmers Market, Creamery Covered Bridge is a classic red bridge with a covered pedestrian walk added in the early 1900s. Built in 1879, it has been bypassed by a new bridge that carries traffic to the popular Living Memorial Park. On a nice afternoon, you might find a group of local musicians practicing inside the bridge.

Only seven miles north of town on Route 30, the 1872 West Dummerston Covered Bridge crosses over the West River. Like Creamery Bridge, it is a Town's Lattice Truss construction, but in two spans. More than three times as long as the Creamery Bridge, at 271 feet it's the longest covered bridge in Vermont that's still in use.

Read More: Vermont in Pictures: Beautiful Places to Photograph

10. Admire the Stone Walls at Scott Farm

The scenic Scott Farm, with its orchards of more than 100 varieties of heirloom apples, is owned by the non-profit Landmark Trust USA, but picking or buying apples is only one reason to visit. The farm is also the training center for the Stone Trust, dedicated to the art of dry stone wall building.

These are not the walls that you'll see along roadsides and fields throughout northern New England, built by long-ago farmers to clear their fields of unwanted rocks. The walls taught here are meticulously crafted and often in ornamental patterns.

Those passing tests for Advanced or Masters certification must build examples of their work, which are incorporated into the farm landscape as the Stone Wall Park.

Stroll through the park and look into the workshop under the massive barn to see wallers at work. If the farm looks a little familiar, it was the main setting for filming Cider House Rules.

On the way to Scott Farm, you'll pass Naulakha, the home built by Rudyard Kipling and where he wrote The Jungle Book.

Address: 707 Kipling Road, Dummerston, Vermont

Official site: https://www.scottfarmvermont.com/

11. Brattleboro Retreat Farm

The picturesque farm overlooking West River was originally intended to provide food, as well as fresh air and activity for patients at the Brattleboro Retreat, a mental health hospital founded in 1834. Today the farm continues to raise animals and crops, with the mission of connecting people to the land.

Along with its historic barns (notice the siding of local slate), you can visit with the farm animals, one of the favorite things to do for families. Sign boards with historic photographs describe the work of the farm and the Retreat, and on weekends, you'll often find food trucks here, along with special programs.

Visitors with children will want to follow the half-mile Storybook Walk near the Piggery, and find the Forest Playground, or you can follow a trail through the riverside meadow filled with pollinator-friendly wildflowers.

This big dairy farm is a perfect location for the large Grafton Village Cheese shop, where you can taste samples of farmstead cheeses from all over Vermont and the world.

Address: Route 30, Brattleboro, Vermont

Official site: https://www.retreatfarm.org

12. Walk or Bike the West River Trail

The three miles of trail beside the West River from Brattleboro to Dummerston follow the bed of the West River Railroad, a line that opened in 1879. While the narrow and winding route between the river and the steep hillside was not an easy one for trains, it is a delightful one for walkers and cyclists.

The trail is level, and the surface relatively smooth, and the fringe of trees opens up regularly for views of the river.

Begin at the Marina below Route 5, just north of the Brattleboro Common. Cyclists can continue north beyond the trail, following the road that replaced the tracks. You'll pass some of the rusting equipment from a former quarry that was served by the railroad.

Official site: www.westrivertrail.org

13. Jelly Mill Falls

More than a cascade, Jelly Mill Falls are a series of low ledges that form a watery staircase interspersed with shallow pools. Stickney Brook is a broad, shallow stream shaded by an arch of trees as it flows over the flat ledges, making it a good spot for a picnic. The shallow pools are safe for children to play in.

Alongside the brook are stone walls of the former mill that gave the falls their name. About 3.5 miles north of Brattleboro on Route 30, you'll see Stickney Road on the left. Just past it is a pull-off space for parking. A trail leads a few yards through the woods to the falls.

14. The Estey Organ Museum

Organs and melodeons made in Brattleboro were once played around the world. Housed in a row of somber gray buildings (the siding on the factory buildings is made from slate), the Estey Organ Company built more than 3,000 pipe organs for churches, theaters, and auditoriums, and more than half a million reed organs. The latter were popular fixtures in fashionable parlors and smaller chapels.

The shop closed in 1960, and the museum preserves its heritage, capturing both the artistry and the musical significance of organs in the 19^th and early 20^th centuries.

If you've ever wondered how a pipe organ works, you can find out here. A 1915 pipe organ from a New Hampshire church has been modified so that visitors can walk inside and see the mechanisms hidden there.

Address: 108 Birge Street, Brattleboro, Vermont

Official site: https://www.esteyorganmuseum.org/

15. Paddle a Kayak on West River

From a launch opposite the Retreat Farm on Route 30, you can paddle in the broad expanses of the West River just before it joins the Connecticut River. The shores of this wide expanse, known as the Retreat Meadows, are prime places to go for bird-watching, and you can paddle upstream as the river narrows somewhat.

Except in the spring runoff, the current is gentle for easy paddling as you pass beneath the striking highway bridge and between the lightly wooded banks. You can rent kayaks, canoes, and paddleboards at the Vermont Canoe Touring Center, on Route 5.

Address: 451 Putney Road (Route 5), Brattleboro, Vermont

Official site: https://www.vermontcanoetouringcenter.com/

16. Go Skiing

The Brattleboro Outing Club, founded in 1922, is a volunteer organization that maintains more than 20 miles of cross-country trails through the forest and across fields overlooking the Connecticut River. You'll find groomed and ungroomed trails, and the club also holds evening ski tours using headlamps. There is a warming hut at the trailhead.

For a few downhill runs on an un-intimidating slope, you can't beat the $5 lift tickets at the Brattleboro Ski Hill in Living Memorial Park. A T-bar lift takes you to the top of an open slope for a half-mile gentle run. When the slope opened in 1937, it was one of only three ski areas east of the Mississippi with a lift.

To watch world champion ski jumpers, come to Brattleboro in February for the annual Harris Hill Ski Jumping Competition, when champions from across the world compete for world records. Wear warm clothes and watch as skiers soar above the 90-meter hill.

Official site: www.brattleborooutingclub.org

Read More:

• Best Places for Cross-Country Skiing in Vermont
• Top-Rated Ski Resorts in Vermont

Map of Things to Do in Brattleboro, VT

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