18 Best Things To Do In Brattleboro, Vermont

“Brattleboro VT. – Creamery Covered Bridge 02” by Daniel Mennerich is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd-nc/2.0/
“Brattleboro VT. – Creamery Covered Bridge 02” by Daniel Mennerich is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd-nc/2.0/

Table of Contents

Welcome to Brattleboro, Vermont, a charming town nestled in the heart of the Green Mountains. Whether you’re a nature enthusiast seeking breathtaking hikes, an art lover in search of creative inspiration, or a foodie eager to indulge in farm-to-table cuisine, this guide will take you on a journey through the best things to do in Brattleboro. From exploring picturesque trails and immersing yourself in the vibrant local arts scene to savoring delectable flavors and discovering the town’s rich history, Brattleboro offers a myriad of experiences that will leave you captivated by its unique charm and natural beauty. Get ready to embark on an unforgettable adventure in this hidden gem of Vermont.

Below are the 18 best things to do in Brattleboro, Vermont:

1. Shop Downtown Brattleboro

“Main Street storefronts in Brattleboro” by randomduck is licensed under CC BY-SA 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-sa/2.0/

Brattleboro, Vermont, is a vibrant hub of activity where you can indulge in a delightful blend of shopping, dining, and craft beer appreciation. Take a leisurely stroll along Main Street, lined with charming boutiques, art galleries, and specialty shops offering a wide array of unique treasures and local crafts. From handmade jewelry to vintage clothing, there’s something for every taste. When hunger strikes, downtown Brattleboro boasts an impressive culinary scene with an abundance of inviting cafes, cozy bistros, and farm-to-table restaurants. Treat your taste buds to locally sourced ingredients, artisanal cheeses, and mouthwatering dishes that showcase the region’s culinary prowess. And let’s not forget the craft beer enthusiasts – downtown Brattleboro is home to several exceptional breweries.

2. Enjoy local food, drinks, and entertainment at Retreat Farm

Retreat Farm is a favorite spot among locals and tourists. The farm is on a mission to connect people to the land in a variety of ways. It consists of nine historic farmstead structures dating back over 180 years. The farm sits on 500 acres of conserved forests, farmland, trails, and waterways. 

There are a number of different activities to enjoy at the farm. Farm tours are always popular and they run every Saturday. The farm tours allow visitors to interact with the animals and learn more about the Farm’s history. Visitors walk through the historic tunnel, walk the meditative labyrinth path of the Hope Garden, admire the farmland, and lastly meet the friendly goats and an ox named Carlos. Another popular activity is the Craft Beer and Cheese Tasting. These occur on Saturdays and visitors get to enjoy a variety of Vermont artisan cheeses expertly paired with a choice of beer, wine, and/or cider. It is a great way to sample a lot of the flavors of Vermont at once! 

A number of events are also held throughout the year at the farm. Throughout the summer the farm runs the Food Truck Roundup event every Thursday in the summer. The event consists of live music, lawn games, a local food truck farm, and craft brews. The event is one of Vermont’s top 10 events and it often does sell out! Another popular event is Music Under the Stars which is a three-part free concert series held at night. Lastly, the Outdoor Art Studio is a wonderful low-cost event that is taught by artist Kate Milliken who focuses on family-focused art-making using foraged and local materials. 

Visitors are also encouraged to walk around the farm and enjoy the interpretive trail system which is essentially an outdoor museum. There are also food trucks at the farm nearly every day throughout the summer and occasionally during the cooler months. Visiting the farm is completely free, but the events and activities do have fees, and often online booking is recommended. 

Address: 45 Farmhouse Sq, Brattleboro, VT 05301

Learn more: retreatfarm.org/ 

3. Go for a nice and easy hike at Fort Dummer State Park

“IMG_3006” by Reggie Martell is licensed under CC BY-NC-SA 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-sa/2.0/

Fort Dummer is a wonderful state park located in the southern part of town. The park has some interesting history as it was the site of the first permanent European settlement in Vermont. Today, the state park spans 217 acres and features a wonderful trail system. There are 3 different hiking trails at the park which range from easy to moderately difficult. These include the Sunrise Trail, Sunset Trail, and the Broad Brook Trail. 

The Sunrise Trail is a nearly one-mile loop trail that traverses even and some gently sloping ground on the eastern edge of the park. The lovely Old Fort Vista is located midway on the trail. The trail is wooded the entire way. The second trail is the Sunset Trail which is a half mile loop route that starts close to the park’s entrance and circles through the play area. It is located on the western side of the property. The Guilford town of Algiers may be seen from the trail’s western perspective. The route traverses on a section of a historic town road that was cut off when the interstate was built, over gently sloping terrain. Along this walk, visitors may observe the remains of the Boyden Farm, which dates to the 1880s. These consist of a farmhouse, a small shed, and stone walls. Lastly, the Broad Brook Trail is a 0.5 mile trail which brings visitors down the brook and to a wonderful swimming hole.

The forest is made of mainly white, red, and chestnut oak trees, but it also contains some beech, maple, white birch, and yellow birch. Since there are so many oak trees, gray squirrels, turkeys, and deer are fond of the area because of the food from the trees. Ruffed grouse have also been known to enjoy the area.

Address: 517 Old Guilford Rd, Brattleboro, VT

Learn morevtstateparks.com/fortdummer.html  

4. Learn something new at the Brattleboro Museum & Art Center

“Brattleboro Museum & Art Center” by MattBritt00 is licensed under CC BY-NC-SA 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-sa/2.0/

A non-collecting museum, the Brattleboro Museum and Art Center was established in 1972. Each season, fresh exhibitions by local and foreign artists are displayed. The museum seeks to inspire, inform, and engage people of all ages via the presentation of art and ideas. Jennifer Bartlett, Chuck Close, Janet Fish, Emily Mason, Wolf Kahn, Chris Van Allsburg, and Andy Warhol are just a few of the renowned artists the museum has shown. The area doubles as a community hub. 

The museum is open Wednesday through Sunday from 10am to 4pm. It is closed on some major holidays, but open on others. Throughout the years, there are usually 15-20 different exhibitions. About 60-70 public programs are launched each year. 

Fun Fact! The museum is actually housed in the old Central Vermont & Boston & Maine Union Station. This railroad station is registered on the National Register of Historic Places because it is representative of the last generation of major railroad passenger station architecture to be constructed in Vermont. Construction on the building began in 1915 and it was finished in 1916. For years, the station served as a major transportation hub in the area. By the 1960s, rail traffic had fallen and in 1966 there were plans for demolishing the station to create a parking lot. Fortunately, a cooperative effort between concerned residents and the Town of Brattleboro saved the building and turned it into a museum and art center. Interestingly, Amtrak established a station at the basement level of the station in  1973 and it remains operational today.

Address: 10 Vernon St, Brattleboro, VT

Learn morebrattleboromuseum.org

5. Walk across the iconic Creamery Covered Bridge

“Brattleboro VT. – Creamery Covered Bridge 02” by Daniel Mennerich is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd-nc/2.0/

There are a lot of great covered bridges in Vermont. Fortunately, the town of Brattleboro is home to the Creamery Covered Bridge which is often considered one of the most beautiful in the state. The historic bridge was first opened in 1879 to carry Guilford Road across Whetstone Brook. It features a stunning Town lattice truss design and has a wonderful bright red paint job. 

The bridge was closed to traffic in 2010 and the town has focused on preserving it ever since. Today, visitors are welcome to walk over the bridge and admire its build quality. There are also some wonderful views of the brook from the walkway. This covered bridge is also known for its seasonal decorations. During the summer and spring, flowers are often planted at the bridge. During the fall, there is stunning foliage surrounding the bridge. When winter comes, the town dresses up the bridge with holiday lights and a lit Christmas Tree inside.

6. Enjoy freshly roasted coffee at Mocha Joe’s Cafe

If you are looking to explore all of Brattleboro, Vermont, you are going to need some energy. There is a lot to cover in this town and when it comes to supplying caffeine, Mocha Joe’s Cafe is the go-to place. Mocha Joe’s is the only specialty coffee roaster and cafe in downtown Brattleboro. Their roasting shop sources specialty, fair-trade, and single-origin beans from all over the world and roasts them right in Brattleboro. Its coffee is renowned throughout the state and many coffee shops in Vermont actually use Mocha Joe’s beans.  

For over 30 years, the Mocha Joe’s Cafe has been serving up cups of freshly roasted coffee. Their roasting shop is located at 35 Frost Street, just a few steps from their cafe at 82 Main Street. It truly doesn’t get any fresher than this! The shop offers coffee, espresso drinks, and freshly baked goods. There is plenty of comfortable seating and also some table games to play with and books to read. This is a great place to quickly drop in quickly for a pick-me-up or spend a few hours. Either way, you can’t go wrong with a stop at Mocha Joe’s! 

Address: 82 Main St, Brattleboro, VT

Learn moremochajoes.com

7. Admire the amazing instruments at the Estey Organ Museum

“Estey Pump Organ (HDR)” by Sensual Shadows Photography is licensed under CC BY-NC 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc/2.0/

When you enter the Estey Organ Museum in Brattleboro, Vermont, an assortment of booming, buzzing, wheezing, and whining will surround you. The town’s organ factory, which produced tens of thousands of them, is honored in the museum. They range in size vastly with some being the size of a briefcase and others being larger than an automobile.. Some are plain, while others are decorated with doilies, pipes, and mirrors. This is not a traditional museum which has strict guidelines around touching. All of the organs on display are there for visitors to play and enjoy. This is truly a one-of-a-kind museum!

Nearly all of the organs on exhibit were constructed less than 200 feet away. At its peak, the Estey Organ Company was one of the most productive organ manufacturers in the world, producing more than 520,000 organs that were sent to practically all parts of the globe. Some of the organs ended up in iconic locations such as New York City’s Capitol Theatre, the Sacramento, CA Municipal Auditorium, and Henry Ford’s home in Dearborn, Michigan. It was by far the best-known manufacturer of reed organs in the world at the time. Manufacturing officially stopped in 1960.

Today, the actual museum is housed in the space that once served as the engine room for an extensive network of assembly lines. The majority of the former plant’s campus is still standing, and it may be recognized by the blue-gray slate tiles that were added to avoid factory fires. There are about 20 buildings in total. 

Visitors are invited to sit down on the vintage benches and play with any of the exhibit models. There are organs for individuals of all sizes and shapes, including miniature ones for young children, and a pipe organ that has been disassembled and is accessible to the public. Historical images and relics are displayed in the museum’s back room to offer visitors an understanding of the different sorts of employees and equipment that operated the factory between 1846 and 1960.

Address: 108 Birge St, Brattleboro, VT

Learn moreesteyorganmuseum.org

8. Pick up provisions at the award-winning Vermont Country Deli 

Country stores are relied upon by locals in Vermont for offering great food and goods. The town of Brattleboro is extremely fortunate to have the Vermont Country Deli. This quaint market offers amazing sandwiches, homemade pastries, snacks, craft beer, gifts, and much more. The store can be found along Western Avenue, just steps from Creamery Covered Bridge. It has been operating since 1986 and has thousands of 5-star reviews online. Although locals are known as being, well, locals at the market, tourists often put the store at the top of their list. 

The bakery is truly world-class at the Vermont Country Deli. One of the most popular items at the store are the fresh cookies. Each cookie is the size of a person’s head and they come in several flavors including chocolate chip, molasses, oatmeal raisin, and peanut butter. Considering their size, they are the perfect fuel for a day of adventuring. The bakery also makes some outstanding rich fudge brownies, tarts, pies, cakes, and giant eclairs with homemade custard. Although you can surely eat cookies for breakfast, the bakery does bake some more traditional breakfast pastries such as giant muffins, scones, flaky croissants, and rich Danish pastries. Calories do not count here!

If you couldn’t guess from the name of the market, the deli is pretty incredible too. For breakfast, the deli produces spectacular breakfast sandwiches with freshly scrambled eggs and a number of great toppings. The lunch sandwiches are truly unforgettable. The team behind the counter has created a number of different signature sandwiches which are all served on freshly baked bread which is made all through the day. Some of the highlights include the Pulled Pork Sandwich with house-made maple barbecue pulled pork along with the Vermont Veggie which features fresh vegetables and an addictive honey mustard sauce. There is also a large to-go counter next to the deli which offers a large assortment of prepared foods including sesame chicken, macaroni and cheese, salads, samosas, and more.

Lastly, the shelves at the Vermont Country Deli are stocked to the brim with amazing local products. There is maple syrup from Highland Sugarworks, Ben & Jerry’s novelty bars and ice cream pints, jams and jellies from Brattleboro’s own Sidehill Farm, candies from Tom & Sally’s Chocolate based in Brattleboro, award-winning cheddars from The Grafton Cheese Company, and much more. Fill up your cart with some of these local goodies to help fuel your travels and truly taste what Vermont has to offer.

Oh, wait! We almost forgot to mention that the fridges at the Vermont Country Deli are stocked up with all of the greatest Vermont craft beers. Produces from all the best Vermont breweries can be found at the store including brews from The Alchemist Brewery, Von Trapp Brewing, Zero Gravity Craft Brewing, and dozens of others. Heady Topper, the iconic beer made by The Alchemist, is often considered the greatest beer in the world and it can often be found in the fridges of the deli.

Address: 436 Western Avenue Brattleboro, VT

Learn morevermontcountrydeli.com 

9. Play a round of disc golf at the Living Memorial Park Course

If you’re looking to spend some quality time outdoors and have some great fun, disc golf is a wonderful activity. Fortunately, the town of Brattleboro has a great course located at the Living Memorial Park. This park is just steps away from the iconic Creamy Covered Bridge. At the park, visitors can enjoy a well-designed 18-hole course. A detailed map can be found at the park’s Course Info Kiosk and also online at brattleborodiscgolf.com

For those unfamiliar with disc golf, it is played like traditional “ball” golf, but with flying discs instead of balls and clubs. One point (stroke) is counted each time the disc is thrown. The goal is to play each hole in the fewest strokes possible. The player with the lowest total strokes for the entire course wins. Play safe by never throwing when players or park users are within range, always give the park users the right away, and be aware of your surroundings and environment. 

Address: 61 Guilford St, Brattleboro, VT

Learn more: brattleborodiscgolf.com

10. Crush local brews at Hermit Thrush Brewery and Whetstone Beer Co.

Breweries and brewpubs can be found all over the state of Vermont, in fact, there are over 70 in the state. The craft brewery movement was sparked in the state during the 1990s by notable breweries such as Magic Hat and Otter Creek. Demand increased for local breweries and others began popping up including innovators like Hill Farmstead and the Alchemist which is the producer of the world-renowned Heady Topper. The town of Brattleboro is fortunate to have two of its own breweries – Hermit Thrush Brewery and Whetstone Beer Co.

Hermit Thrush Brewery is located at 29 High Street and it has been fermenting with only wild Brattleboro mixed culture yeast since 2014. The brewery capitalizes on the availability of world-class hops and fruits in the region to create truly incredible products. All of the beers produced at Hermit Thrush are New American Sours and utilize 100% wild yeast. The taproom is open several days a week for pours, flights, and beer to-go. Well-behaved dogs are welcome in the taproom but must be leashed. There is also a limited food menu offered, but visitors are welcome to bring food too! It should be noted that the company does put a lot of effort into making beer sustainably. Some of these efforts include packing beer in light cans and packages, using a high efficiency biomass wood pellet boiler system, lighting facilities with LEDs and motion sensors, and having a Sustainability Coordinator consistently pursue new sustainability initiatives. Not a huge beer fan? They have a great selection of hard seltzers too!

Hermit Thrush Brewery Address: 29 High St #101c, Brattleboro, VT 05301  

Hermit Thrush Brewery Websitehermitthrushbrewery.com/

Whetstone Beer Co. is another great brewery located in Brattleboro at 36 Bridge Street. This riverside brewery and eatery offers wonderful craft drafts, creative pub grub, and year-round deck seating. The brewery began as a small taproom in Brattleboro in 2006. After several years of great beers being produced, the Whetstone team decided to expand in a big way. In 2011, Whetstone Beer Co. began building out a world-class brewery and restaurant on the banks of the Connecticut River. Since 2012, the Whetstone Station Restaurant and Brewery has been serving amazing food along with handcrafted beers. At Whetstone Station, visitors can enjoy great brews along with awesome comfort food including pulled pork mac and cheese, a dozen different handcrafted burgers, artisan hot dogs, and plenty more. The brewery at the restaurant pumps out over 1,000 kegs of beer each year and almost every drop of it is sold on-site. Due to a rise in demand for the beer, the company opened up a dedicated production brewery on 39 Frost Street in Brattleboro in the summer of 2019. This allows the company to produce cans and kegs for the best bars, restaurants, and retail shops in the state. 

Whetstone Beer Co. Address: 36 Bridge St, Brattleboro, VT

Whetstone Beer Co. Websitewhetstonebeer.com

11. See some amazing sights from the water with the help of the Vermont Canoe Touring Center

While in Brattleboro, visitors often spend a lot of time near the waterways, especially the Connecticut River which runs parallel to Brattleboro’s Main Street. The best way to truly enjoy the river is to get out on it and go for a paddle. That is where the Vermont Canoe Touring Center comes in. The center is conveniently located at the confluence of the West River and the Connecticut River. 

The Connecticut River is a wonderful place to paddle and the Vermont Canoe Touring Center offers visitors the opportunity to rent canoes, kayaks, and paddle boards. Although the Connecticut River is a large river, it is very safe to paddle around because of the Vernon Dam which is seven miles south of the center. This dam controls the water level and current, so on most days it is just like paddling on a calm lake. Although some days after heavy rain can have a little current, the West River is always protected and calm. 

All of the watercraft can be rented by the hour or for a full day. No prior experience is needed considering the water is typically super calm and easy to navigate. The center takes care of putting the boats in the water along with taking them out. All you have to do is show up and paddle! It’s an unforgettable experience getting to enjoy the lovely waterways of Brattleboro.

Address: 451 Putney Rd, Brattleboro, VT

Learn morevermontcanoetouringcenter.com

12. Spend a night camping at the Fort Dummer State Park

Vermont is a beautiful state full of many amazing campgrounds. Luckily, Fort Dummer State Park offers a great campground and it is located just down the road from Brattleboro’s Main Street. The campground features 50 tent/RV sites along with 10 lean-to sites. All of the campsites are located in a circular formation with amenities located in the middle. In regards to amenities, there are two toilet buildings, coin-operated hot showers, a sanitary dump station, and a picnic table. Additionally, there are fire pits, charcoal grills, and picnic tables at each campsite. Spend the day exploring and wind down at the campground with smores at the firepit. Nothing better! 

Address: 517 Old Guilford Rd, Brattleboro, VT

Learn morevtstateparks.com/fortdummer.html 

13. Hike the beautiful Woodlands Interpretive Trail at the Retreat Trails

The Retreat Trails of Brattleboro are well-liked among locals and tourists alike. There are several different parking options and a few different trails. Many hikers park at Retreat Farm which has direct access to the miles of trails. All of the trails are well-marked and well-maintained. There is a donation box at all of the information kiosks and donations help hugely with the maintenance of the trail system. 

One of the most popular trails is the Woodlands Interpretive Trail. This is a 1.2-mile loop trail that takes hikers to all of the best spots within the expansive trail system. It is rated as easy and typically takes 30-40 minutes to complete. Parking is available right off Western Avenue adjacent to The Neighborhood Schoolhouse. Two of the highlights of this trail are the stops at the Harris Hill Ski Jump and the Brattleboro Retreat Tower. Both of these sites have fascinating histories. 

The Harris Hill Ski Jump is a fascinating structure found along the Retreat Trails and visitors are welcome to walk around the jump during the non-winter months. The original jump was built in 1922 at a cost of $2,200 and that year a skier broke the New England ski jump distance record. The jump went on to host many ski jump events including many invitational meets, Vermont State Championships, New England Championships, and National Ski Jump Championship. In 1934, a special train route was created to bring ski jump spectators from New London, CT all the way to Brattleboro. During several winters, a bus would run from Main Street Brattleboro to the jump in order to make commuting easier for skiers and onlookers. Over the years, many different additions were made to the jump to keep it functional. The 90-meter Harris Hill Ski Jump was eventually completely rebuilt in 2008 to International Ski Federation specs. The jump renovations cost $600,000 but were well worth it to honor its rich history and support its future events.

The other unique structure along the Retreat Trails is the Retreat Tower. Although the tower is beautiful, it has a very dark past. The tower was constructed in 1887 by patients of the former VEermont Asylum for the Insane which was located along Linden Street. (Much of the former asylum was renovated to create the Brattleboro Retreat mental health hospital which is still running today). The doctors at the insane asylum believed that fresh air and physical activity were key in helping patients dealing with mental issues. To help stimulate their minds and provide exercise, the doctors instructed many of the male patients to construct the Retreat Tower. It was built to be an observation tower that would offer sweeping views of the surrounding area. Upon completion, the tower did offer great views, but it also led to an unintended result. Several patients of the Vermont Asylum for the Inane jumped off the top of the tower and plumped to their deaths. It was quickly closed and abandoned. Today, the tower remains standing and remains locked up. It is in pretty rough condition, so no climbers are allowed inside. 

Address: 231 Western Ave, Brattleboro, VT

Learn morealltrails.com/trail/us/vermont/woodlands-interpretive-trail 

14. Shop all of the greatest local products at the Brattleboro Farmers Market

“Farmer’s Market, Brattleboro, VT – IMGP5947” by catchesthelight is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd-nc/2.0/

Every Saturday from 9am to 2pm from May to October, the famous Brattleboro Area Farmers’ Market takes place. This is no regular farmers market. It is a well-loved and organized community event that brings together all the best locally grown produce, prepared food, handmade crafts, and more from Windham and Cheshire counties.

Each year there are some new vendors, but most have been showcasing at the market for many years. The full list of vendors can be found on the official Brattleboro Farmers Market website. Some of the highlights of the 2023 farmers market are Vermont Gelato, 

True North Granola, High Meadows Farm, and Hidden Bean Bakeshop. There are over 50+ full-season vendors in total that offer everything from organically grown vegetables and crepes to wood-laminate earrings and handcrafted body care products. Some additional vendors also visit throughout the summer. This is a wonderful market to shop at to see all that southern Vermont has to offer and to load up on outstanding products!

Visiting during the winter? Check out the Brattleboro Winter Farmers Market!

Address: 570 Western Ave, Brattleboro, VT

Learn morebrattleboroareafarmersmarket.com

15. Take a dip at the Broad Brook Swimming Hole 

“First dip o’ summer at Fort Dummer State Park.” by okaygallagher is licensed under CC BY 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by/2.0

If you visit Brattleboro during the summer, the odds are you will break a sweat. There’s a lot to do in this charming Vermont town from hiking, eating, drinking, and shopping. If you’re looking to cool down for a few minutes, then you must visit one of the local swimming holes. The Broad Brook Swimming Hole is one of the greatest options in town.  

This swimming hole can conveniently be found along a trail in Fort Dummer State Park. To reach the swimming area, take Broad Brook Trail. This half-mile trail descends from the campground to the popular swimming hole. The trail is steep in sections but should be manageable for most abilities. It takes about 10 minutes to reach the swimming hole from the trailhead. 

Address: 517 Old Guilford Rd, Brattleboro, VT

Learn morevtstateparks.com/fortdummer.html  

16. Enjoy a concert at The Stone Church

For many years, both native-born and immigrant musicians and artists of international renown have called Brattleboro, Vermont, home. However, there has also long been a need for a suitable location that would enable these musicians to perform locally and receive support. That’s where The Stone Church comes in. The Stone Church is Brattleboro’s premier music venue and it is located in… well, a stone church. 

The beautiful Victorian Gothic church was formerly the All Souls Unitarian church. After church operations ended in the 1960s, it was used for a variety of uses until it was transformed into a music venue. The team behind The Stone Church completely restored and renovated the church. All of the patina and soul of the 150-year-old building was retained while adding new features to make it a modern music venue. Since opening, The Stone Church has become Southern Vermont’s premier live music and event venue. 

The Stone Church hosts hundreds of events every year. Their full schedule can be viewed on their website. Musicians of all types are welcome to perform at the venue. One night there can be 100 people in chairs listening to folk music. Then next night there can be a hardcore rock band complete with an open moshpit. It is truly one of the greatest venues in the state and any visitor to Brattleboro should check who’s performing during their visit.

Address: 210 Main St, Brattleboro, VT 

Learn morestonechurchvt.com

17. Learn about everything related to maple syrup at the Vermont Maple Museum

“Giant Maple Syrup Bottle” by jimmywayne is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

The New England Maple Museum and Gift Shop is a wonderfully unique experience that is both entertaining and educational.  Over 100 feet of murals, which were hand-painted by a local artist, portray the development of maple sugaring from Native American times to the present.  Along with models and a short film, the museum’s exhibitions also feature the largest collection of maple sugaring artifacts known to exist. Enjoy a taste of Vermont’s official flavor, maple syrup, afterward too!

A variety of maple-flavored treats, including syrup, cream, candies, cookies, caramels, popcorn, and even jelly beans, are available in the specialty Vermont gift shop at the museum. The shop also sells locally created food, Vermont-made trinkets, and hand-made artisan gifts that are all manufactured here in Vermont. Cap off a trip to the Vermont Maple Museum by taking a group photo with the largest jug of maple syrup in the world, which can be found on the front lawn of the museum. This is a perfect place to load up on goodies and learn a lot!

Address: 1991 Marlboro Rd, Brattleboro, VT  

Learn moremaplemuseum.com

18. Enjoy some amazing jazz at the Vermont Jazz Center

“Antonio Hart” by Professor Bop is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd-nc/2.0/

The premier jazz venue in New England is the Vermont Jazz Center.  Three things are prioritized by the organization: 1) world-class jazz concerts; 2) a wealth of educational programs; and 3) community involvement. The goals of all three of these initiatives are to improve rural Vermont’s standard of living and culture.

The Jazz Center is proud of the outstanding level of talent present in its concert calendar. The VJC’s schedule also features musicians who frequently appear at the Kennedy Center, Dizzy’s at Jazz at Lincoln Center, and the Village Vanguard. The Chamber Music America Acclaim Award, given in 2014 to the VJC, honors “extraordinary cultural contributions in a locality or region.” NEA award winners Sheila Jordan, Kenny Barron, Dave Liebman, Dr. Lonnie Smith, and Jimmy Heath are just a few of the musicians and ensembles that have played here. Jazzmeia Horn, Snarky Puppy, Helen Sung, Pedrito Martinez & Alredo Rodriguez, Fred Hersch, and many others are additional notable artists.

For visitors looking to enjoy the center, there are many workshops and concerts that occur throughout the year. Schedules of events can be found on the Vermont Jazz Center’s website. All concerts are held in the center’s state-of-the-art 250-seat performance hall.

Address: 72 Cotton Mill Hill, Brattleboro, VT

Learn morevtjazz.org

Best Hotels and Lodging Options in Brattleboro

There are several different ways to stay in Brattleboro including campgrounds, hotels, inns, and Airbnbs. Below are some of the best options to choose from.


Fort Dummer State Park – This great state park that offers many camping sites. There are 50 tent/rv sites along with 10 lean-to locations. Each campsite has a firepit, picnic table, and grill. Communal amenities include two bathrooms, coin-operated showers, and a dumping station.

Brattleboro North KOA Journey – One of KOA’s three locations in Vermont. The Brattleboro North KOA Journey offers several different lodging options. There are simple tent camping sites, full hookup RV sites, and deluxe cabins. Many great amenities can be found at the campground including Wi-Fi, a pool, 24/7 laundry, propane, a pavilion, a dog park, and a camp store. 


Inn on Putney Road Bed and Breakfast – This inn is often rated as the greatest place to stay in Brattleboro and this can be seen by the hundreds of 5-star reviews on Google, Tripadvisor, and Booking.com. The Inn on Putney Road is located just a short walk from downtown Brattleboro and it offers 6 elegant waterside rooms. There are great common areas including a game room, garden, and a kitchen. Speaking of the kitchen, all guests can enjoy a complimentary 2 or 3-course gourmet breakfast each morning.

Hampton Inn Brattleboro – The Hampton Inn is another solid lodging option in Brattleboro. This is just a stranded chain hotel, but it is known for its good prices, nice rooms, and great amenities. Some of the key amenities include a free hot breakfast, free wifi, a fitness center, an indoor pool, and pet-friendly rooms. The Hampton Inn is conveniently located just off Route 91 and guests are just a short walk away from popular stores and attractions. 

Latchis Hotel – For travelers looking to stay right in the heart of Brattleboro, Latchis Hotel is the go-to option. This Art Deco treasure is located right at the corner of Main Street and Flat Streets in the center of town. Steps from the hotel, visitors have easy access to breweries, shops, coffee roasteries, and more. The hotel offers comfortable rooms that blend vintage and modern. Amenities include free Wi-Fi, a 24-hour coffee bar, a conference room, and a pub.


Cozy Cabin Retreat on the River – A great option for a group who is looking for a comfortable, spacious, and updated rental home. The Cozy Cabin Retreat offers 3 bedrooms and is capable of accommodating 8 guests. The renovated open and cozy home is situated within walking distance of the heart of Brattleboro. High ceilings, memory foam beds, and brand-new appliances can be found throughout the house. There is also a  private and peaceful fire pit setup located right on the banks of the river. This is one of the best places to unwind after a day exploring Brattleboro!


Quiet Street Apartment – This is a wonderful option for any couple or solo traveler visiting Brattleboro. Quiet Street Apartment is one of the highest-rated Airbnbs in the area and it offers everything needed for a wonderful stay. There is a private entry, up wide covered stairs to open and enclosed porches, into a newly renovated spacious open-concept living and kitchen area. A separate large bedroom with a queen-size bed has French doors that open onto the enclosed porch. A short walk to downtown restaurants, food coop, and shops, walking distance to trails.



“Greetings from Brattleboro, Vermont – Large Letter Postcard” by Shook Photos is licensed under CC BY 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by/2.0/

As you conclude your journey through this guide to the best things to do in Brattleboro, Vermont, you’ve likely discovered the town’s captivating charm and diverse offerings. From immersing yourself in the natural beauty of the Green Mountains to exploring the vibrant arts scene and savoring the delectable farm-to-table cuisine, Brattleboro has undoubtedly left a lasting impression. Whether you’re seeking outdoor adventures, cultural experiences, or culinary delights, this hidden gem of Vermont has it all. With its picturesque landscapes, welcoming community, and rich history, Brattleboro offers an escape from the ordinary and invites you to embrace the extraordinary. So pack your bags, follow this guide, and embark on an unforgettable journey to discover the best of Brattleboro, Vermont.

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Tom Riley

Hi! I'm Tom. I am the creator of GoXplr. I started this website with a focus on helping people explore better and explore more. I am based in New England and obsessed with traveling. Here at GoXplr, you will find expert blog posts and also maps containing all of the best places to explore. These blogs and maps have taken thousands of hours to complete. I hope you enjoy this resource and it inspires you to get out and explore!

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