Located in Southern Vermont on the bank of the Connecticut River, Brattleboro is a popular four-season tourist destination, with excellent skiing, snowshoeing and skating in the winter, and swimming, tennis, golf, hiking and biking in the summer. Brattleboro, VT is home to the Brattleboro Museum & Art Center, the Tasha Tudor Museum, the Estey Organ Museum and other cultural institutions. Here are the best things to do in Brattleboro, Vermont.

1. Creamery Covered Bridge

Creamery Covered Bridge
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The Creamery Covered Bridge, also known as the West Hill Covered Bridge, or the Crystal Springs Covered Bridge, is a beautiful covered wooden bridge within the town of Brattleboro and is the only surviving example of such a bridge in the region. Constructed in 1879 of spruce lumber, the Creamery Covered Bridge is named after a creamery that was located adjacent to the bridge site, and consists of a single span bridge 80 feet long and 19 feet wide supported by two flanking timber lattice trusses, with a covered sidewalk attached to the eastern side of the span.

The bridge is listed on the National Register of Historic Places and a popular tourist attraction that attracts visitors from all over to take in the beautiful scenery.

Guilford Street off Route 9 west, over Whetstone Brook, Brattleboro, VT 05301

2. Brattleboro Museum & Art Center

Brattleboro Museum & Art Center
© Brattleboro Museum and Art Center

Founded in 1972, the Brattleboro Museum and Art Center is a non-collecting museum that showcases works by regional and international artists to inspire, educate, and engage visitors of all ages. Located in the former Union Station in downtown Brattleboro, the Museum and Art Center’s collection includes works by Wolf Kahn, Andy Warhol, Chuck Close, and Janet Fish, as well as special exhibitions from local school groups and other community organizations.

The Museum also offers educational and school programs for lifelong learning, guided tours and gallery walks through the museum, and can be rented for special events.

10 Vernon St, Brattleboro, VT 05301, Phone: (802) 257-0124

3. Retreat Trails

Retreat Trails
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Located south of Green Mountain National Forest, the Retreat Trails are accessible networks of trails that wind through the forested and hilly area north of the Massachusetts border. The trail system is over nine miles long, covering more than 400 acres of forest and agricultural land and include some unusual sites, such as the old Cemetery and the Retreat Tower.

Ranging from old jeep roads to winding single tracks, the Retreat Trails cater for all levels, from easy trails for beginners and families to challenging single tracks, with some trails leading up to the top of the town’s ski jump, which boasts spectacular views of the surrounding countryside. Several of the trails still have the names they were given 175 years ago when they were created for the use of the patients and staff of the “Vermont Asylum”, which is in operation today as the Brattleboro Retreat.

4. Brattleboro Area Farmers' Market

Brattleboro Area Farmers' Market
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The Brattleboro Area Farmers' Market is a premier farmers market that features over 50 vendors selling a range of agricultural products, arts and crafts, live music and animals and ethnic foods from around the world. The market is Southern Vermont's main farmers' gathering, and offers both locals and visitors a crash course in Vermont food with a range of free-range beef and lamb, cheeses, fruit and veggies, honey, maple syrup, and freshly baked pastries.

The Brattleboro Area Farmers' Market is held every Wednesday and Saturday between 9 am – 2 pm (please confirm the hours before you go). Saturday's market is located just west of town by the Creamery Bridge and Wednesday's is held on the Whetstone Pathway off Main Street.

Western Ave, West Brattleboro, VT 05301, Phone: (802) 254-8885

5. The Retreat Farm

The Retreat Farm
© The Retreat Farm

The Retreat Farm is a historic farm and nonprofit center that focuses on conservation, education, recreation, and sustainable enterprise for the community. The Farm is an authentic reflection of the rural way of life in Vermont, and offers hands-on farming experiences for the whole family, including petting goats, playing with chicks, feeding sheep and playing in the corn.

The petting farm allows children to interact with a variety of animals and learn more about life on a farm while a gift shop offers an array of souvenirs to take away. The Retreat Farm is also home to one of the five trailheads that make up the nine-mile Retreat Trails recreation network, which is open year-round for hikers, bikers, horseback riders and skiers.

45 Farmhouse Square, Brattleboro, VT 05301, Phone: (802) 490-2270

6. Fort Dummer State Park

Fort Dummer State Park
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Nestled in the Connecticut River Valley, the Fort Dummer State Park is home to 217 acres of scenic forest land and is named after Vermont’s first permanent European settlement. It is characterized by its unique forest which is unlike that of the usual Vermont forest, and more akin to fauna one might find in New England’s southern regions. At the end of the day, the best way to enjoy and maximize this state park is to explore its many trails, one of which ends at a refreshing swimming hole, and another which leads to an overlook that features breathtaking views of the original Fort Dummer site. At the end of the day, pitch a tent and spend the night under the stars as you enjoy the warmth of a campfire and great company.

517 Old Guilford Road, Brattleboro, Vermont 05301, Phone: 802-254-2610

7. Estey Organ Museum

Estey Organ Museum
© Estey Organ Museum

The Estey Organ Museum was established in 2002 to celebrate the heritage of Estey Organ Company of Brattleboro. Named after Jacob Estey, who founded the largest Estey reed, pipe, and electronic organ manufacturing establishment of its kind, the Museum is dedicated to preserving and sharing historical information about the company, its products, and practices through excellent collections and exhibits of Estey and other organs.

Celebrating the craft business of the Estey Organ Company’s organ production, which was a familiar name from the late 1800s through the 1950s, the museum encourages visitors to explore and learn about music, craft industries, social history and more through the permanent collection of artifacts, housed in the old Engine House of Estey Organ Company. The museum also sponsors special events, traveling exhibits and a variety of activities, including organ restoration workshops, musical concerts, and historical re-enactments.

108 Birge Street, Brattleboro, VT 05301, Phone: (802) 246-8366

8. KidsPLAYce: Southern Vermont Children's Discovery Center

KidsPLAYce: Southern Vermont Children's Discovery Center
© KidsPLAYce

KidsPLAYce is a family-friendly and fun-filled indoor play-space for children from ages 0-8, that offers an interactive and immersive environment in which children can learn through play. Imaginative and creative displays and exhibits are designed to engage, inspire, and encourage exploration and discovery, such as a musical marimba bench, a pirate ship, zoom tubes and a life-size castle. If you are wondering what to do in Brattleboro with kids, this is a great place to visit.

A dedicated space is also available for infants and toddlers, which features a unique puppet stage, colorful murals by local artists and soft play areas. A casual and comfortable lunch time area offers a safe and inviting space in which to enjoy healthy snacks and drinks. A variety of programs and events throughout the year can be enjoyed by all, including ‘Visit with Santa’ and ‘Fine Dining Raffle’.

20 Elliot St, Brattleboro, VT 05301, Phone: (802) 254-5212

9. Twice Upon a Time

Twice Upon a Time
© Twice Upon a Time

Twice Upon a Time is a family-owned and operated business that sells a broad range of vintage and collectible items from the 18th Century to the present. The shop is based in a beautifully restored historic turn-of-the-century department store, and covers 10,000 square feet of space with the original mezzanine level.

The store offers a wide selection of collectibles, furniture, home décor, glass, china, and vintage clothing sourced from over 100 dealers and 4,000 consignors. Twice Upon a Time offers consignments and rental spaces, as well as local deliveries and pickups.

63 Main St. Brattleboro VT, 05301, Phone: (802) 254-2261

10. Top of the Hill Grill

Top of the Hill Grill
© Top of the Hill Grill

Top of the Hill Grill is a family-friendly restaurant that serves authentic pit barbecue food, including hickory smoked pulled pork, beef brisket and ribs, grilled chicken and smoked turkey, and freshly ground, pure beef burgers. Delicious prime cut meats are accompanied by a range of freshly made salads and sides such as baked beans, coleslaw, roasted potatoes, root vegetables, and cornbread. Vegetarians are also catered for, with a variety of pasta and non-meat dishes available. For an added bite, try the Mexican and Cajun specialties of fajitas, quesadillas, gumbo, chili and jambalaya.

An exclusive Kid’s Menu offers favorites such as hot dogs, burgers, chicken fingers, mac and cheese and sloppy joes. A beautiful wooden deck with picnic tables offers spectacular outdoor dining in the summer, while an indoor heated deckhouse provides warmth and coziness in the winter without losing the magnificent views.

Williamsville, VT 05362, Phone: (802) 258-9178

11. Whetstone Station Restaurant and Brewery

Whetstone Station Restaurant and Brewery
© Whetstone Station Restaurant and Brewery

Whetstone Station Restaurant and Brewery is a waterfront restaurant that serves creative cuisine food, local craft beers, and refreshing signature drinks in a picturesque riverside setting. Just a short stroll from downtown Brattleboro, Whetstone Station boasts year-round indoor and outdoor dining against a backdrop of breathtaking views.

The menu offers traditional pub grub-style fare from starters of grilled sirloin tips, crab cakes, and pub pretzels, to mains of spiced cider ribs, basil encrusted salmon, pub meatloaf and classic fish and chips. Lighters meals such as burgers and sandwiches are available from the ‘Brew Bar’ menu while a range of handcrafted beers from the brewery can be enjoyed with every meal. The intimate brewery can be explored with guided tours and tastings on the first Sunday of each month at noon, or by appointment.

36 Bridge Street, Brattleboro, VT 05301, Phone: (802) 490-2354

12. Brattleboro History Center

Brattleboro History Center
© Brattleboro History Center

The Brattleboro History Center is dedicated to showcasing items and artifacts collected by the Brattleboro Historical Society, that focus on the history and heritage of the Brattleboro area.

Located on the first floor of the Masonic building on Main Street, the History Center features a range of exhibits that explore the agricultural history and farm life of the former Valley Fair, including model railroads and bridges, vintage toys, important business signs and newspapers, a miniature replica of Fort Drummer and various paintings.

230 Main Street, 3rd Floor, Phone: 802-258-4957

13. Hermit Thrush Brewery

Hermit Thrush Brewery
© Hermit Thrush Brewery

Hermit Thrush Brewery is a local brewery that creates Belgian-inspired and barrel-soured ales and fruit beers. Founded by Christophe Gangné and Avery Schwenk in 2014, the brewery has quickly gained a reputation for noteworthy sour and wild ale recipes, which are made using sustainable processes and renewable energy.

The beautiful little brewery exudes old-world style with exposed brick, elegant archways and a quaint tasting room made out of reused wood where visitors can enjoy tasting flights of a variety of beers, including Brattlebeer, Silly Friar, Dizzy Vicar, Party Guy and Brooks Brown. In addition to fantastic tours and tastings, Hermit Thrush also showcases works of art by local artists. This stop is for visitors over 21.

29 High Street Suite 101C, Brattleboro, VT 05301, Phone: (802) 257-BEER

14. Dosa Kitchen

Dosa Kitchen
© Dosa Kitchen

Dosa Kitchen is a food truck owned by cookbook author, Leda Scheintaub which serves a creative menu of South Indian cuisine. Located at the Grafton Cheese Village in the heart of Brattleboro, Dosa Kitchen boasts a farm-to-table ethos that forms the background of this delicious ethnic cuisine, in particular, the dosa- a crispy, tangy fermented rice and lentil crepe, that is created and served from the truck’s tiny kitchen.

Made-from-scratch dosas range from the traditional masala dosa and the non-traditional kimchi bacon dosa pancake to the signature dosa dog – a large pork and beef hot dog wrapped in a thick dosa and stacked with tangy homemade mustard, masala sauerkraut, and Grafton cheddar cheese. Dosa Kitchen is available for private parties and events, and caters for all types of dietary requirements from gluten- and diary-free to vegetarian.

Grafton Cheese Village, 400 Linden Street (on Route 30) in Brattleboro, Vermont, Phone: (646) 388-2221

15. Saxtons Distillery

Saxtons Distillery
© Saxtons Distillery

Old-world heritage and the unique flavors of Vermont come together in perfect harmony at the Saxtons Distillery. Owned by Christian Stromberg, the distillery was born out of his family’s desire to keep their Lithuanian traditions alive – particularly when it comes to making fantastic and flavorful liqueurs. The distilling techniques used by the Saxtons Distillery have stood the test of time, having passed down from generation to generation, and making the distillery what it is today – one of the most popular places to try and purchase spirits in Brattleboro. The distillery’s spirits have been featured in the press several times including Esquire, LA Weekly, and the Portland Press Herald, so guests to the taproom can be sure that they’re in for a treat. Try favorites like their Sapling Maple Liqueur, the Snowdrop American Dry Gin, and the Perc Coffee Liqueur.

155 Chickering Drive, Brattleboro, Vermont 05301, Phone: 802-246-1128

16. T.J. Buckley's Uptown Dining

T.J. Buckley's Uptown Dining
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Located in a beautifully restored Worcester Dining Car from 1925, T.J. Buckley’s is a family-friendly restaurant, which serves seasonal organic cuisine created with ingredients sourced from local farmers and producers. Headed up by Chef-Owner Michael Fuller, T.J. Buckley’s menu offers a range of ever-evolving New American cuisine with a European touch taken from Chef Fuller’s classic French training across a variety of foods, including meat, fish, poultry, vegetables and gluten-free foods.

Delicious, freshly prepared salads precede every signature meal, which include Rabbit Loin wrapped in Serrano ham and Maine heirloom beans, winter vegetables, and poached Bosc pear and Crispy Pork Belly with Diver Scallops served with gritty polenta cake, steamed winter greens, and black trumpet mushrooms in carrot oil and aged balsamic syrup. The restaurant’s open kitchen and vintage décor evoke a quintessential Vermont dining experience with soft lighting and a casual, laid-back ambiance. T.J. Buckley’s is open for dinner Thursday through Sunday year-round, and seasonally on Wednesdays.

132 Elliot Street, Brattleboro, VT 05301, Phone: (802) 257-4922

17. Peter Havens

Peter Havens
© Peter Havens

Peter Havens has been one of Brattleboro’s most popular dining establishments for over 20 years. Started by Thomas Dahlin and Gregg Van Iderstine, the restaurant presents a warm and welcoming atmosphere, an inspiring menu of excellent cuisine and wine, and outstanding service. The modest eatery only holds ten tables where diners can enjoy romantic dinners in a casual, cozy ambiance and has a bar where signature cocktails can be enjoyed before or after dinner.

The menu presents an array of comfort food, including starters of Sesame Crusted Ahi Tuna, Wild Maine Mussels steamed in white wine, and brandy and vermouth marinated escargots sautéed with garlic, entrées of pan-roasted duck breast with French greens, salmon steak with ginger soy vinaigrette, and grilled lamb chops in a rosemary marinade. End with something sweet from the dessert menu, such as chocolate mousse, warm apple tart or Nantucket oatmeal spice cake and sip fine wines from around the world from the impressive wine list.

32 Elliot Street, Brattleboro, VT 05301, Phone: (802) 257-3333

18. Superfresh! Organic Cafe

Superfresh! Organic Cafe
© Superfresh

Located at the base of Mount Wantastiquet on the banks of the Connecticut River, the cafe serves 100% vegetarian/vegan cuisine and is the only restaurant in southern Vermont to do so. Boasting a commitment to a delicious, healthy and affordable menu, this family-friendly eatery presents a menu of homemade soups and freshly prepared salads, delicious sandwiches, wraps, burritos and quesadillas, pizzas and other healthy hearty entrées, and raw desserts.

Add a beverage from the variety of freshly squeezed fruit and vegetable juices, smoothies, coffee and tea and enjoy your meal in the comfy, casual restaurant against a backdrop of live music and local artworks. In addition to using locally sourced ingredients and supporting regional farmers and producers, the Superfresh! Kitchen is also committed to supporting sustainable models of production, distribution, waste and recycling and has a small retail space which sells artisanal shelf-stable food products and herbal apothecary goods.

30 Main St. Brattleboro, VT, Phone: (802) 579-1751

19. The Robb Family Farm Sugar House

The Robb Family Farm Sugar House
© The Robb Family Farm Sugar House

Vermont has always been known for its spectacular maple syrup, but when if you want to experience and purchase the best maple products that the state has to offer, then a trip to The Robb Family Farm Sugar House is in order. The farm was established by Thomas and Christine Betterly in 1907 and interestingly was originally a dairy farm. It wasn’t until 2011 that the farm said goodbye to their dairy operations to focus entirely on their maple syrup products. Visitors to the farm can learn about the traditional process of collecting maple sap and the subsequent work that takes place to transform the sap into maple syrup. Guests can also learn about the differences in maple syrup’s three grades and try samples of it to boot. Of course, no trip to the Robb Family Farm Sugar House isn’t complete without a trip to the gift shop where jugs of maple syrup, maple candy, maple coated nuts, and even maple ice cream, can be purchased.

822 Ames Hill Road, Brattleboro, Vermont 05301, Phone: 802-257-0163

20. Brattleboro Outing Club

Brattleboro Outing Club
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In 1922, a local sports enthusiast by the name of Fred Harris founded the Brattleboro Outing Club with one mission in mind: to encourage and promote greater community participation in outdoor sports and activities. Today, the Brattleboro Outing Club is one of the country’s oldest outdoor sports civic associations and hosts regular events and activities throughout the year. The club focuses on four distinct outdoor activities in particular: tennis, rowing, cross-country skiing, and paddling. Guests to the club can enjoy the use of six exceptionally maintained red clay tennis courts or try their hand at rowing down the West and Connecticut Rivers on club-owned rowing boats or participate in group kayaking or canoeing trips. In the winter, the club also offers skiing and snowshoeing activities along many miles of breathtaking trails. Each program is situated at different locations throughout the city while their activities can be booked ahead of time. Phone: 802-246-7843

21. The Marina

The Marina
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What could be better than feasting on fresh seafood and juicy burgers at the waterfront after an exciting day out on the water? At the Marina Restaurant, hungry diners can do exactly that with the bonus of a stunning panoramic view and even more gorgeous sunsets. The restaurant can be found at the foot of the West River Trail and dishes up fantastic American fare in a casual dining atmosphere from Wednesday to Sunday. The Marina’s menu landed it a feature on the Food Network with crowd-pleasers like the Grilled Mahi, the Cioppino, and the Fried Mahi Tacos. Make sure to try offerings from The Marina’s appetizer and dessert menu as well for an epic start and sweet finish to your meal.

28 Spring Tree Road, Brattleboro, Vermont 05301, Phone: 802-257-7563

22. 118 Elliot

118 Elliot
© 118 Elliot

Capable of accommodating 220 guests within its 2000-square foot space, 118 Elliot is a landmark institution of education and arts appreciation that is situated in the center of Brattleboro’s downtown area. Visitors to 118 Elliot can enjoy a variety of events related to creative arts, musical arts, and educational talks, in addition to perusing lovely works of art that can be found displaced on its walls. Outside of the event space, there is a great forest garden to be enjoyed, and has been host to many outdoor events. Be sure to check ahead of time for events being held at 118 Elliot to avoid disappointment.

118 Elliot Street, Brattleboro, Vermont 05301, Phone: 917-239-8743

23. Harris Hill Ski Jump

Harris Hill Ski Jump
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The Harris Hill Ski Jump is more than just a winter sporting event, it’s practically an institution. After all, world-class ski jumpers and fans of the sport have descended upon Harris Hill annually to see fantastic sportsmanship and athleticism since 1922. Harris Hill’s jump is 90 meters long and gives skiers the boost they need to soar as high as 300 feet into the air and awesome speeds, some as fast as 60 miles per hour. Because of this, Harris Hill has hosted a number of international competitions including 9 national championships and Olympic qualifying events. Truly, for fans of the sport, this historic event is certainly an item to add to the bucket list.

Cedar Street, Battleboro, Vermont 05301, Phone: 802-254-2565

24. Boys and Girls Club of Brattleboro

Boys and Girls Club of Brattleboro
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The aim of the Boys and Girls Club of Brattleboro is simple – to enable the youth to blast past their limitations and reach their full potential. They do this by providing recreational activities and companionship to young boys and girls who would otherwise often be left at home with no care or supervision. There are a great number of club programs and services that the club’s members can enjoy such as skateboarding, camps, cycling programs, and after-school programs like the Kid’s Club. The Boys and Girls Club of Brattleboro is open Monday through Friday and is open to first-time visitors who would like to know more about what the club has to offer.

17 Flat Street, Brattleboro, Vermont 05301, Phone: 802-254-5990

25. Wheelhouse Clay Center

Wheelhouse Clay Center
© Wheelhouse Clay Center

Unleash your creativity and craftiness at the Wheelhouse Clay Center, a popular center for clay arts in the beautiful city of Brattleboro. Wheelhouse Clay Center is co-owned by Teta Hilsdon and Shari Zabriskie, both of whom have decades of experience when it comes to teaching clay arts and managing a top clay studio. Though the studio is often rented by potter hobbyists or professionals who need a space to produce their products, visitors who are new to the clay arts can participate in fun hands-on classes that are taught by knowledgeable artists. Participants can opt to sign up for one-of classes, or a series of workshops, depending on what they want to accomplish. Classes to try include the Wheel Throwing for Beginners, Outdoor Barrel Firing workshops, and Hand Building workshops.

48 Harmony Place, Brattleboro, Vermont 05301, Phone: 802-490-2693

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