April 17, 2024

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Complete Guide To Discovering Brattleboro’s Vermont Charm

Complete Guide To Discovering Brattleboro’s Vermont Charm

Just an hour north of Springfield, another American history hot spot, lies Brattleboro, Vermont. The picturesque small town is a haven buried in the great outdoors of New England and one of the most beautiful towns in Vermont every traveler should visit.

On the border of New Hampshire along the banks of the Connecticut River, Brattleboro boasts lovely parks, a proud arts scene, and a lively downtown. Although small, it is the perfect weekend getaway from the bustling and Instagrammable Boston or a day stop on a road trip along the East Coast.

Brattleboro was originally Fort Dummer: the first European settlement in Vermont. While the former fort flooded and was buried by the river, Brattleboro emerged as a cultural gem in southern Vermont. The small town endeavors to highlight its past and integrate it into the present day. History buffs, outdoor enthusiasts, and cultural connoisseurs will all be enchanted by Brattleboro.

Find the complete guide here.

Top 9 Things To Do In Brattleboro

A storied past, a burgeoning art and culture scene, and a rural setting nestled in the forests of Vermont give tourists a lot to see and do in Brattleboro.

Among many other activities, visitors can wander through museums, attend concerts, or get out into the great outdoors. Brattleboro is one of the perfect small towns for a weekend trip in Vermont.

14 Cross The Creamery Covered Bridge

Creamery Covered Bridge

The bright red Creamery Covered Bridge at the Living Memorial Park in Brattleboro, Vermont

A significant and historical tourist attraction in Brattleboro is the Creamery Covered Bridge. The iconic, bright red bridge is just west of downtown and crosses the Whetstone Brooke near the Living Memorial Park.

Constructed in 1879, the bridge is a relic of America’s past and the last standing 19th-century covered bridge in Vermont. The bridge formerly served for traffic but now is a tourist attraction for photographers and selfies.

Travelers can taste a piece of the past by crossing the bridge. Later, visitors can bike or stroll along the nearby streets and parks.

Related This Vermont Town Has The Most Covered Bridges (Here’s How To See Them)

13 Browse Galleries At The Brattleboro Museum & Art Center

Contemporary Art Museum
Via: Tapio Haaja on Unsplash

A bright and colorful display at a contemporary art museum

Art enthusiasts will love the opportunity to wander through the Brattleboro Museum & Art Center. Located in the former Union Station in downtown Brattleboro, the vibrant contemporary art museum is free to visit.

Focused on modern art, the museum annually displays fifteen to twenty new exhibits, including paintings, sculptures, and photography. The museum attracts regional and international artists, uplifting and nurturing the cultural scene in southern Vermont.

Educating and inspiring guests aside, the museum is also available to rent for special events and offers lifelong learning programs for children.

  • Hours Of Operation:
    Wednesday – Sunday, 10 AM – 4 PM

    | Closed Mondays & Tuesdays

  • Cost Of Admission:

  • Note:
    Closed certain holidays

12 Breathe Fresh Air At Retreat Farm And Forest

Vermont Farmhouse
Via: Venti Views on Unsplash

A farmhouse buried in Vermont woods and fall foliage

Visitors don’t have to travel far to escape into nature near Brattleboro. Less than a mile northwest of downtown, the Retreat Farms and Forests connect guests with Vermont’s abundant outdoor scenery.

Hikers will appreciate the ten miles of winding trails through forests, meadows, and along the river. Journeyers looking for a challenge can hike to the top of Harris Hill Ski Jump. Families can instead explore the half-mile Nature Trail.

The spooky Stone Tower looms above the forest, a stone lookout constructed in 1887 by and for asylum patients. Its purpose was to bring patients into nature as part of their treatment, but the tower is enveloped in paranormal activity and local haunted folklore accounts.

Additionally, children will enjoy the pasture animals, storybook walk, and playground at the Retreat Farm.

  • Hours Of Operation:
    Daily, dusk – dawn

  • Cost Of Admission:

Related This Vermont Mountain Ghost Town Has A Chilling History

11 Brattleboro Area Farmers’ Market

Farmers' Market
Via: Erik Scheel: https://www.pexels.com/photo/person-giving-fruit-to-another-95425/

A vendor handing over fruit at a bright Farmers’ Market

Farmers’ Markets are often the best way to experience the spirit and culture of a town.

The Brattleboro Area Farmers’ Market is an animated outdoor market with over forty stalls. The market runs from May to October on Saturday mornings, and visitors can find it near the Creamery Covered Bridge.

Shoppers can browse fresh produce, flowers, and baked goods while enjoying live outdoor music. Also offering unique and global stalls, tourists can find French macaroons, authentic Indian spices, and hand-crafted pottery at the Brattleboro Area Farmers’ Market.

  • Hours Of Operation:
    Saturdays, May – October, 9 AM – 2 PM

  • Note:
    $2 fee for charges made at stalls accepting credit cards

    | Cards can be used at the manager’s booth to purchase tokens

10 Watch A Film At The Latchis Theater

Vintage Theater
Via: Donald Tong: https://www.pexels.com/photo/theater-interior-109669/

A vintage theater empty except for one person

The Latchis Theater is a cultural gem adorning Main Street in downtown Brattleboro. The Greco-Deco-style theater opened in 1938 and began by screening silent films and Vaudeville.

Inside, Greek paintings, red-velvet curtains, plush seats, and an intricate Zodiac on the ceiling marvel visitors. Part of the League of Historic American Theaters, The Latchis Theater showcases performances and modern cinema.

Travelers should admire the theater’s interior at a live event, a movie screening, or rent it out for a special occasion.

  • Movie Ticket Prices:
    $10 per adult | $8 for seniors and children 11 & under | $8 for all matinee tickets

  • Note:
    Accessible for people of varying abilities

9 Go Hiking At Fort Dummer State Park

Vermont outdoors
Via: John Holm on Unsplash

A scenic image of a river and trees dressed in fall foliage in the Vermont outdoors 

Travelers who wish to continue their adventure in Brattleboro outdoors should visit the Fort Dummer State Park.

The state park lies two miles south of Brattleboro and is the former site of the first European settlement in Vermont: Fort Dummer. While the fort was flooded and buried by the Connecticut River, outdoors enthusiasts can still enjoy many recreational activities at the park.

The expansive area has three short hiking trails (one to a swimming hole) and several camping areas fortents or RVs, including toilet facilities and hot showers.

The park is a peaceful place to enjoy the Vermont wilderness and hike, dog walk, or camp.

  • Hours Of Operation:
    Daily, 6 AM – 9 PM

  • Cost Of Admission:

8 Follow The Words Trail

Via: Pixabay: https://www.pexels.com/photo/aerial-view-architecture-autumn-cars-280221/

High angle of a rural village on a bright day 

Throughout the ages, the charm of Brattleboro and its bucolic surroundings have been a fountain of inspiration for great minds like politicians, writers, and poets.

History buffs can learn stories from this rich past while visiting their physical sites on the Brattleboro Words Trail.

The Words Trail is an interactive map on an app that users can follow throughout downtown Brattleboro and the encompassing countryside. The downtown section has over forty sites, each site including photos, links, and five to seven-minute audio entries.

These locations include petroglyphs from the Native American Abenaki community, Frederick Douglas’ first speech on the assassination of Lincoln, and Rudyard Kipling’s favorite watering hole.

A testament to Brattleboro’s pride in history and culture, the local community manages the Words Trail and produces the audio entries. Visitors can find physical ceramic maps of the Word Trail downtown.

British author Rudyard Kipling wrote his renowned novel The Jungle Book while living in Brattleboro.

Related Vermont’s Historic Landmarks: Tracing The State’s Rich Colonial & Revolutionary Past

7 Estey Organ Museum

Via: Eric Mok on Unsplash

An impressive and looming classic organ piano 

From the late 1800s until the 1950s, the Estey Organ Company was globally renowned for its masterful organs.

Operating out of Brattleboro, Estey organs could be found across six continents, and throughout its prime, the company hand-crafted over 3,000 pipe organs and over half a million reed organs.

Today, visitors can browse the memorabilia and instruments from the Estey legacy at the Estey Organ Museum downtown. The museum will fascinate everyone from organ aficionados to architectural and social historians.

A hands-on museum, the Estey team encourages guests to bring music and try out the historic organs.

  • Hours Of Operation:
    Saturdays, May – October, 2 PM – 4 PM

  • Cost Of Admission:
    $5 requested donation

  • Note:
    Most people spend about 30 minutes at the museum

6 Attend A Concert At The Stone Church

Stone Church
Via: Maryna Nikolaieva on Unsplash

Stone church in black and white on a rainy day 

Metal heads will rejoice at Brattleboro’s grooviest attraction: The Stone Church.

The 19th-century stone church rests innocently on Main Street in downtown Brattleboro. Gothic revival style with Scandinavian and Renaissance influences, the church belonged to All Souls Unitarian until it was recently converted into an auditorium.

Today, concert-goers pilgrimage to this sanctuary in the Vermont woods to hear their favorite bands and experience sensational acoustics. Preserved stained-glass windows, a remolded stone entryway, and a stage made from reconverted pews represent Brattleboro’s dedication to integrating the past into the cultural present.

The Stone Church has attracted metal, rock, and indie pop acts.

5 Best Time To Go To Brattleboro

Vermont scenery
Via: Kevin Davison on Unsplash

Rolling Vermont fields into mountains and undulating hills

Brattleboro experiences the highs and lows of each season. The small town caters to all travelers and offers something unique and enjoyable any time of the year.

Despite its adaptability, the best time to visit Brattleboro is in the summer when the temperatures are most pleasant, and warm-weather travelers can enjoy outdoor recreational activities.

  • Best Time To Visit Brattleboro:
    June – August

  • Temperatures:
    Highs from 79° – 82°

    | Lows from 54° – 57°

Traveling to Brattleboro during the summer means warm days and cool nights, excellent weather for hiking, camping, biking, or strolling downtown.

Tourism is at its highest from June to August, so travelers should book well in advance to avoid higher prices.

While the fall gets cool and rainy, with highs in the 50s and lows in the 30s, Brattleboro is an epic starting point for experiencing some of Vermont’s most scenic fall drives. November is the slowest month for tourism, meaning accommodation prices are generally more affordable.

Winter travelers should pack mittens, scarves, and coats because Brattleboro knows the cold. There is a high probability of snow, and temperatures can drop to 10° at night and waver in the 30s during the day.

Fortunately, Vermont is a winter paradise. Sparkling snow-capped mountains and forests define the state from December into February, perfect for scenic winter drives in Vermont. Recreational activities include snowshoeing, skiing, ice fishing, and ice skating.

Lastly, springtime travelers will be met with gradually warming temperatures and more rain. May is the rainiest month, and temperatures can vary from lows in the 20s to highs in the 70s.

4 Best Ways To Get Around In Brattleboro

Dirt Road in Vermont
Via: Aditya Vyas on Unsplash

A gravel road weaves through forests decked out in fall colors in Vermont 

The best way to get around in Brattleboro is a mix of walking and driving.

The downtown is small and highly walkable. Travelers can conveniently go on foot between museums, shops, restaurants, and accommodations.

Downtown attractions aside, the natural surroundings offer hiking and walking trails, like the Retreat Forest, Fort Drummer State Park, and the Living Memorial Park.

Brattleboro is inseparable from the encompassing New England wilderness, so visitors will want a car to easily explore the nearby state parks or venture further into Vermont’s abundant outdoor attractions.

Many hotels in Brattleboro offer free parking, but the town also has ample metered street parking spaces and lots.

While the city streets in Brattleboro are not exactly bike-friendly, the nearby city and state parks have excellent bike routes. The downtown also offers many bike racks.

Travelers can arrive in Brattleboro from the rest of the East Coast by Greyhound Bus Lines and Amtrak Trains.

3 Where To Eat In Brattleboro

Cozy Restaurant
Via: Nick Zheng on Unsplash

Cozy wooden restaurant looking out into the woods


Brattleboro may be small, but the town packs a big culinary punch. Chain restaurants and fast food joints aside, Brattleboro has everything from animated cafes, home-style barbecues, intimate fine dining, and quaint bars.

Breakfast Spots In Brattleboro

The Porch Cafe & Catering is a lively and bright breakfast place near downtown Brattleboro. Guests order from chalkboard menus at the counter and stay for great conversation and classic American hearty breakfast plates.

The cafe also serves baked goods and unique lunch items, such as Bahn mi sandwiches.

  • Hours:
    Monday – Thursday, 7 AM – 3 PM | Closed Friday – Sunday

  • Cost:

  • Address:
    648 Putney Rd, Brattleboro, VT

  • Recommended:
    Egg sandwich | Waffles | Omelets | Vegetarian

Lunch Locations In Brattleboro

Top of the Hill Grill is an excellent lunch restaurant in Brattleboro, with stunning views of the Connecticut River and the woods of New Hampshire.

The homey joint serves authentic pit barbecue meat with savory home-style sides. The restaurant offers a wooden deck for laid-back summer dining and a heated indoor deckhouse for cozy winter meals.

  • Hours:
    Thursdays, 3 PM – 8 PM | Friday – Sunday, 11 AM – 8 PM | Closed Monday – Wednesday

  • Cost:

  • Address:
    632 Putney Rd, Brattleboro, VT

  • Recommended:
    Cajun catfish | Rice & beans | Wraps | Vegetarian & vegan options

Dinner Restaurants In Brattleboro

T.J. Buckley’s offers guests a quiet and intimate dinner in Brattleboro. The restaurant is in a remodeled Worcester Train Dining Car, and its vintage decoration and open kitchen design emanate a classic yet casual atmosphere.

The menu changes seasonally and sources local and organic ingredients. Classically trained in France, the chef serves modern American cuisine with a timeless European touch.

  • Hours:
    Thursday – Sunday, 5:30 PM – 9 PM | Closed Monday – Wednesday

  • Cost:

  • Address:
    132 Elliot St, Brattleboro, VT

  • Recommended:
    Crab cakes | Scallops | Rabbit

Related Savor The Flavors Of Vermont: A Culinary Journey Through Farm-To-Table Cuisine

Drinks In Brattleboro

Hermit Thrust Brewery is a quaint bar and brewery in Brattleboro known for Belgian-style beers and barrel-aged sours. The brewery feels like home with its exposed brick walls and wooden archways.

Visitors can enjoy a beer tasting or buy cans of local beer to take home. Craft beer lovers may decide they’ve found one of the best breweries in Vermont.

  • Hours:
    Thursday – Saturday, 11 AM – 7 PM | Sundays, 11 AM – 8 PM | Mondays, 11 AM – 7 PM

  • Cost:

  • Address:
    29 High St #101c, Brattleboro, VT

  • Recommended:
    Sours | Craft beer tastings

2 Where To Stay In Brattleboro

Intersection in Brattleboro
Via: MoneyforCoffee in Pixabay

Intersection of High Street and Main Street in Brattleboro, Vermont

Tourists can find most hotels in Brattleboro downtown, lodging in quiet rooms along the Connecticut River. The small town doesn’t have several options, but that doesn’t mean guests sacrifice quality.

Due to a lack of competition, the prices don’t vary much from one hotel to the other.

Luxury Stays In Brattleboro

Holiday Inn Express Hotel & Suites

  • Prices Starting At:

  • Why You Should Book:
    Indoor pool | Fitness center | Free parking

Mid-tier Stays In Brattleboro

Riverside Hotel Ascend Hotel Collection

  • Prices Starting At:

  • Why You Should Book:
    Three-star hotel | Fitness center | Free parking

Related Bang For Your Buck: Book A Stay At These 10 Cool Vermont Backpacker Hostels

Budget-friendly Stays In Brattleboro

Econo Lodge

  • Prices Starting At:

  • Why You Should Book:
    Indoor pool

    | Free parking

Road trippers and campers can stay at the Fort Dummer State Park campsites for more rustic accommodation.

1 How To Spend The Perfect Day In Brattleboro

River in Brattleboro
Via: NT Franklin on Pixabay

The woods of New Hampshire and Vermont are divided by the Connecticut River in Brattleboro on an overcast day

Brattleboro should be on every traveler’s list of the smallest towns to visit in Vermont. Despite its small size, Brattleboro guarantees visitors a fulfilling day trip destination.

The perfect morning in Brattleboro begins downtown with a coffee and hearty breakfast at The Porch Cafe. Fueled for the day, visitors can spend the morning at one of Brattleboro’s cultural attractions, like the artsy Brattleboro Museum & Arts Center, the historical Words Trail, or the musically-inclined Estey Organ Museum.

Tourists should complete the morning with a stroll in the Living Memorial Park and cross the iconic Creamery Covered Bridge. If it happens to be a Saturday from May to October, explore the Brattleboro Farmers’ Market.

A day in Brattleboro wouldn’t be complete without venturing into the crisp Vermont wilderness. Fortunately, Brattleboro is surrounded by woods, and hikers can walk the trails at Retreat Forest or Fort Dummer State Park. Families can visit the kid-friendly attractions and pasture animals at Retreat Farms.

Finally, tourists should conclude their perfect day in Brattleboro by returning downtown. Lively bars and restaurants guarantee visitors a night well spent, followed by a concert at the Stone Church or a movie at Latchis Theater.


Q: Is Brattleboro, Vermont worth visiting?

Brattleboro is worth a visit for a day trip in Vermont or a stop along a road trip through New England. The quaint small town boasts a lot of charm.

Visitors can browse galleries at the Brattleboro Museum & Art Center or follow an interactive map of historical sites downtown along the Words Trail.

Hikers can visit one of the top state parks in Vermont just outside of Brattleboro: Fort Dummer State Park.

Q: Is Brattleboro walkable?

Downtown Brattleboro is compact and walkable. Tourists can reach several dining options, shops, entertainment venues, and accommodations on foot. Additionally, the downtown has convenient Amtrak and bus stations to get travelers around to surrounding state parks or cities.

Visitors can pair some of Vermont’s best breweries with hiking trails in Brattleboro. Hikers can explore the Retreat Trails just north of downtown and later walk to Hermit Thrust Brewery for craft beers.

Q: What is there to do in Brattleboro in the winter?

Brattleboro is a four-season southern Vermont travel destination. Winter travelers can enjoy ice skating, cross-country skiing, ice fishing, and snowshoeing in the state parks near Brattleboro.

In addition, Brattleboro is surrounded by some of Vermont’s best ski resorts.