Regional Spotlight | Brattleboro and Surrounding Windham County
Situated in the southeastern corner of the state, Brattleboro is the largest town in Windham County and serves as an artistic and economic anchor for the region. The Round and Black mountains bring texture to Brattleboro’s skyline while the Connecticut River rushes through the town’s heart, lending a lively atmosphere to a historic downtown lined with storied architecture and brick buildings.
The town has the dynamic feeling of a story still in progress. In 2023, Brattleboro was named Strongest Town in the U.S. by StrongTowns.org, noting places “doing the hard but rewarding work of making their communities stronger and more resilient.” Brattleboro’s small-town vibe combines with easy access to greater New England; Windham County is a multi-state area, with both Massachusetts and New Hampshire within a 15-mile drive of Brattleboro. Three covered bridges lend historic significance to Brattleboro, and nearby, the Green Mountain Forest adds nearly 400,000 protected acres of natural beauty and outdoor recreation to the surrounding region.
Life in Brattleboro means being part of a tight-knit community dedicated to continuous reinvestment. “There is something about Brattleboro that you can just feel. Everything about Brattleboro is intersectional, from its location at the confluence of two rivers to its history as a working mill town and now the arts and culture hub of southern Vermont. Brattleboro buzzes with a feeling of possibility. It’s the kind of place where ideas are celebrated and community comes together to support each other,” said Kate Trzaskos, executive director of Downtown Brattleboro Alliance. Brattleboro’s annual calendar is lively with art and cultural events like Gallery Walk, a monthly art celebration with food trucks, live music, and pop-up art stations that brings the whole downtown together.
The original Harris Hill Ski Jump was built in 1922, and every winter, crowds come together to watch jumpers compete there. Brattleboro Museum and Arts Center curates and exhibits contemporary art from regional and internationally known artists, and nonprofits like Epsilon Spires work to advance performing and visual arts within Brattleboro and throughout the region. The premiere circus training school in the U.S., New England Center for Circus Arts is built into the region’s culture with adult workshops, youth classes, and community performances.
Prior to European settlement, Brattleboro and its surrounding area was known to the Abenaki as Wantastegok, meaning “At the river where something is lost.” The Atowi Project works to create a place-based center to engage with the broader community, starting with a land acknowledgement at Retreat Farm, 140 acres of original Indigenous land.
Chartered in 1753, Brattleboro developed quickly after war ceased with British and French troops. In the early 1800s, it was among Vermont’s most thriving towns for business, a legacy that continues today. Now the largest Vermont town on the New Hampshire border, Brattleboro is home to about 12,000 people, and Windham County is home to about 47,000. Brattleboro residents have access to a wide variety of employment opportunities, including in the arts, health care, hospitality, and manufacturing sectors. Within a commutable distance, there are as many job opportunities in the Brattleboro area as there are in Burlington, and comparatively low traffic makes a commute more accessible.
Nearby, Community College of Vermont and Vermont State University both have satellite campuses in Brattleboro, offering accessible education in fields like health care, animal studies, hospitality, working lands, engineering, and more, as well as the opportunity to work in education. Businesses like Mocha Joe’s Coffee Roasters, which brought home a 2023 Vermont Business Magazine Best in Business Award, Hermit Thrush Brewery, Whetstone Beer Company, and Against the Grain Gourmet, a gluten-free manufacturer, illuminate the town’s innovative and culture-conscious food and beverage industry. Work in tourism and hospitality can be found at Mount Snow, nearby Stratton Mountain Resort, or a plethora of lodging properties and guest experiences in southeastern Vermont. Find manufacturing work at GS Precision, Inc., Chroma Technologies, or ROV Technologies. Brattleboro Memorial Hospital provides compassionate and cutting-edge health care to southeastern Vermont residents. Coworking spaces like Vermont Innovation Box and several new spaces in development make it easier for professionals to share office space and infrastructure. Woodworkers can share space and equipment at HatchSpace.
Brattleboro is a nexus for both Vermont life and access to greater New England, with the state lines of Massachusetts and New Hampshire, within 15 miles of the town. Amtrak’s Vermonter line, with a stop in Brattleboro, offers daily service to New York City and Washington, D.C. Connecticut’s Bradley Airport is a little more than an hour away, offering easy access to direct national and international flights. The Moover bus offers fare-free service, connecting Brattleboro to the rest of the region.
Printing was among Brattleboro’s chief economic drivers in the 1800s, with one of the largest printing establishments in New England moving to its downtown in 1890, even printing for Yale University Press. The Brattleboro Words Trail is a great way to immerse yourself in the town’s literary history, including stops significant to Rudyard Kipling, who wrote The Jungle Book at his Brattleboro home. A former church has been newly renovated into a live music venue, hosting everything from rambunctious metal shows to intimate folk gatherings at the Stone Church. Recently, Epsilon Spires, with help from a Better Places grant from the Vermont Department of Housing and Community Development, worked to facilitate the painting of a mural on the High Street wall to beautify the downtown. Nearby, another Better Places grant funded the construction of a brand-new community park in Guilford featuring a timber-frame pavilion, a labyrinth, a fire pit, a playground, and a basketball court.
Local residents enjoy life-work balance, including access to healthy local food and nearby outdoor recreation. The Brattleboro Area Farmers Market brings the regional community together to enjoy live music, explore and purchase locally grown produce, prepared foods, and handcrafted goods from Windham County and the surrounding area. Downtown, the River Garden Marketplace brings together craft food and beverages, live music, and a market to create a community meeting space under a dramatic glass ceiling. Five hundred acres of forests, farmlands, and conserved trails await at Retreat Farm, free and open to the public every day from dawn to dusk, where you’ll find a weekly food truck roundup in the summer, outdoor art studio, and natural and agricultural education for all ages. Those looking for diversity in dining will find it at Yalla Vermont, serving vegetarian and Mediterranean food, or on Blue Moose’s Italian menu.
Nearby, Fort Dummer State Park offers 217 acres of public land for recreation including hiking, biking, camping, and swimming, as well as views of a historic Revolutionary War fort that was the site of the first permanent European settlement in Vermont. The 16-mile West River Trail appeals to a wide variety of users, including equestrians, cyclists, and walkers. Find community with rowing, tennis, cross-country skiing, and paddling at the Brattleboro Outing Club, and at Bonnyvale Environmental Education Center, two miles of public trails are just the beginning. Kids of all ages can participate in nature education camps, clubs, and after school activities, programs and events invite the public to learn about the southeastern Vermont ecosystem, and volunteers can take part in conservation planning and rehabilitation efforts. In the winter, Brattleboro Ski Hill is a community mainstay. Entirely volunteer-run, including snowmaking and grooming, the town ski area has a T-bar that’s perfect for kids to learn and trails for the whole family. In nearby West Dover, Mount Snow offers 1,700 feet of vertical drop served by 19 lifts, as well as 10 terrain parks. About an hour from Brattleboro, Stratton Mountain Resort has 99 trails, glades, and fast lifts.
The Brattleboro community stands ready to welcome newcomers. Brattleboro has adopted the Declaration of Inclusion, reinforcing its status as a safe and welcoming place for all. Downtown nonprofit Out in the Open works to connect rural LGBTQ+ people with community and a broader network of support. The Southern Vermont Young Professionals meet monthly for social, recreational, networking, and volunteer opportunities. In Brattleboro, organizations like Windham and Windsor Housing Trust, Brattleboro Housing Partnerships, and Brattleboro Area Affordable Housing are always working to add more housing stock to the market, like a planned 300-unit housing development announced in January 2023. “We have a wide range of desirable neighborhoods and homes suiting various lifestyles from footloose empty nesters in the Brattleboro Brooks House to rural homes within moments of downtown, trails, or ski slopes,” said Jennifer Stromsten, director of programs at Brattleboro Development Credit Corporation.
Considering relocating to Brattleboro? Get in touch with a local real estate agent to see what’s available and keep up with the local newspaper, the Brattleboro Reformer. New residents and those considering making a move can also browse SoVermont.com for professional and relocation resources, and start your job search on the Brattleboro Area Chamber of Commerce’s local board. The Southern Vermont Economy Summit offers networking opportunities and educational sessions annually in Brattleboro. Help with relocating or starting up a business, from real estate solutions to technical assistance and lending, is available at BrattleboroDevelopment.com. Programs both statewide and region-specific can help potential new Vermonters find information, answers to their questions, and planning resources for a move. Kick off a job search by browsing positions currently open in Vermont. Economic development tools, incentives, and special programs can also help those looking to expand or relocate their businesses to Vermont. Connect with a Vermonter to ask questions about relocating.
