Brattleboro attracts both artists and outdoor enthusiasts
On the southeastern edge of Vermont, Brattleboro started as a trading gateway along the Connecticut River before developing into a bookbinding and pipe organ manufacturing town in the 1800s. Today, the small town of about 12,000 residents offers both an artsy and outdoorsy way of life. “We’re a service town for the more rural areas around our outskirts, and city folk have found us, so we’ve become more desirable,” says Christine Lewis, a local broker at Brattleboro Area Realty. “Our landscape is lumpy; we have hills and valleys that give us nice views and waterways. The town is well-laid out with nature preserves all around us, so we also attract outdoorsy and active people.” In addition to hiking trails and green spaces, this Windham County town offers ski slopes and boat ramps.
Brattleboro’s industry seamlessly transformed from industrial to creative, as more artists, musicians and authors moved to the area. Art galleries and music venues neighbor Main Street’s trendy boutiques and eateries. “We are considered kind of a hippie town. During the war draft years, a lot of young people with a conscience came to Windham College, which was a liberal arts college," Lewis says, referring to what is now Landmark College about 10 miles north of town. “We ended up with a rich base of artisans and intellectuals, and that formed Brattleboro up to this day. Now we have a lot of professionals who work from home and go to the city once a week.” Thanks to Interstate 91 zipping through town, these commutes are more manageable.
Downtown’s Main Street is lined with eateries and art galleries
Brattleboro’s town center is populated on the east side, where Vermont kisses the Connecticut River. This bustling downtown area is lined with retail and dining along Main Street, while art centers and galleries dot the surrounding streets. “We have a lot of quality restaurants. On one strip of Main Street, there are a couple of restaurants with outdoorsy river views, like Echo. It appeals to a wide variety of palates, has an outside deck and serves drinks,” Lewis says. “And at the foot of Main Street, there’s Superfresh Organic Cafe, which draws in people who are vegetarian or organic.” Mocha Joe’s is a popular coffee shop, and Peter Havens is an upscale American bistro. For post-dinner drinks, Kipling’s Tavern is an intimate Irish bar with a pub menu. And for groceries, locals can shop at the Brattleboro Food Co-Op. “People will go south to Massachusetts to shop because we don’t have a mall or a retail center,” Lewis notes.
Residents can also find entertainment around Battleboro proper’s east side, from music venues to art galleries. The Stone Church hosts live music in a refurbished Victorian Gothic church, and Brattleboro Museum and Art Center is a donation-based museum in a former train station. “Main Street does a gallery walk on the first Friday of every month, with not only galleries but art displayed in every downtown shop,” Lewis says. “It’s like a community party year-round, no matter the weather. You always run into somebody you know, and the restaurants are always open and willing to play.” Another way for creatives to gather is through the Brattleboro Literary Festival, which is held at various downtown locations. The annual event allows local authors to showcase their literature and connect with fellow writers. “Brattleboro is well known for its upper end musicians, artists and writers. They’re all tucked in the town, and you don’t necessarily know where they are. But they come out for events like these.”
Explore the town through Living Memorial Park and Retreat Farm
Brattleboro residents can enjoy a variety of outdoor activities at Living Memorial Park, the community’s main green space. The park has a playground, athletic fields, tennis and pickleball courts, a disc golf course, a dog park and an outdoor pool. Winter brings different recreation, as locals can use the park’s ski slope and ice-skate at the Nelson Withington Skating Facility. The Historic Creamery Bridge, built in 1879, is part of Vermont’s covered bridge tour. Brattleboro Country Club is the town’s public 18-hole golf course and driving range, and on the other side of the Connecticut River, Norm’s Marina offers boat ramps and dock slips. Also just across the river, Wantastiquet Mountain provides miles of hiking and biking trails.
For a family-friendly interactive nature experience, Retreat Farm offers 500 acres of preserved land. In addition to walking the 10 miles of forested and interpretive trails that pass historic barns, towers and other landmarks, residents can visit animals in pasture and explore the Forest Playground. The barn on-site hosts regular wine- and cheese-tasting events. As a celebration of the Indigenous Peoples who founded this land, originally called Wantastegok, Retreat Farm preaches that their space belongs to everyone and not just one sole entity.
Homebuyers can find historic Victorians and spacious farmhouses
Depending on their location in Brattleboro, housing styles vary from charming Victorians to sprawling farmhouses. “In Battleboro proper, there are glorious old Victorians with the woodwork and fancy colors, and there’s also eclectic bungalows that were built with unique pieces shipped to town on the railroad.” In addition to Victorian-styles in need of renovations, many have been fixed up and marketed as investment opportunities for multiple tenants. Buyers can find 1,000- to 5,000-square-foot properties with two to eight units from around $210,000 to $745,000. Single-family Victorians and Colonial-era homes with antique architecture and modern interiors, many with detached garage additions, range in price between $320,000 to $700,000. “You also have your farm-style houses, which we call New Englanders, built from the 1700s to the 1900s,” Lewis says. “Some have been restored and are just lovely, while others are still working farms and not as fancy.” These farmhouses on the outskirts of town can start around $780,000 for 12 acres and rise to almost $3 million for nearly 45 acres.
Students attend schools in Windham Southeast Supervisory Union
Students in Brattleboro are part of Windham Southeast Supervisory Union, which receives a C-plus rating from Niche. Learners can begin at Oak Grove School, which also receives a C-plus. They can progress to Brattleboro Area Middle School before advancing to Brattleboro Union High School, both of which receive a B-minus. The high school partners with the Windham Regional Career Center to offer students three academy pathways: STEM, Visual Performing Arts and International Studies. A local private school option, Saint Michael Catholic School serves kindergarten through twelfth-grade learners. The school is affiliated with Saint Michael’s Catholic Church across the street, which stands tall in a red brick Victorian-era building with a towering spire.
Interstate 91 connects commuters to nearby New England cities
Interstate 91 runs north-south through Brattleboro, connecting residents to the surrounding cities. As alternate thoroughfares, U.S. Route 5 runs parallel to the interstate, and State Route 9 cuts east-west through town. For cross-country and international destinations, Bradley International Airport is about 80 miles south and Boston Logan International Airport is about 110 miles southeast. “Most people head south to Bradley in Connecticut because it’s easier to get to,” Lewis says. “But some choose Boston or New York if they’re doing international flights.” The Brattleboro train station provides Amtrak Vermonter service to Washington D.C., with stops at Hartford, New York City and Philadelphia. MOOver is a free Southern Vermont bus shuttle that services Windham County, and the local Brattleboro Memorial Hospital is a full-service community hospital.
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