Guilford’s close-knit community in Southern Vermont
Just south of Brattleboro, Guilford is a rural Vermont town that hugs the Massachusetts border. “Guilford is the first stop in Vermont for people coming up from Massachusetts,” says Trent Stephens, a Realtor with Wohler Realty Group. As the gateway to Vermont, travelers cruising along Interstate 91 are greeted with lush rolling hills, quiet rural roads and local farms that source everything from lumber to maple syrup. “Guilford used to be one of the smaller towns in Vermont, but its proximity to Brattleboro has made it a more popular bedroom community,” Stephens says.
Founded in the 18th century, Guilford was once the stage of a mini-revolution dubbed the “Guilford War,” when New York refused to give up its territorial rights to Vermont post-Revolutionary War. Today, Guilford is a close-knit community with around 1,600 residents. The Guilford Gazette, an all-volunteer quarterly magazine mailed to every household, helps keep everyone connected. “It’s the kind of place where houses are spread out, but everyone still knows their neighbors,” Stephens says. Town meetings are still central to local life, and newcomers are quickly welcomed into the community. Its proximity to Brattleboro offers convenience, but the town itself remains rural with a low CAP Index Crime Score of 1 out of 10.
Local green spaces, state parks and country retreats
The Guilford Community Park sits in the heart of the village center, which sits at the intersection of U.S. Route 5 and Guilford Center Road. This popular green space is home to a playground, fire pit and a labyrinth, an intricate design made from natural elements for walking meditations. The park also boasts a wooden pavilion that’s often used by the neighboring Guilford Community Church for family game nights and Sunday morning worship services. Up the road, Fort Dummer State Park’s 217 acres of dense woodlands feature hiking trails and campsites.
About 7 miles southwest, another small town center along Guilford Center Road is home to the local historical society, a library and a recreation center. The Broad Brook Community Center offers a jam-packed event calendar with activities like ukulele lessons, art workshops, yoga classes and tai chi.
The community center is about 3 miles from Green River Village, a historic settlement in western Guilford. Bucolic country landscapes give way to a wooden, red covered bridge that sits adjacent to the Green River Timber Crib Dam, creating a small waterfall and swimming hole. The dam and local establishments like the Green River Church and Green River Village Center are overseen by the Green River Preservation Trust.
Secluded homes in the countryside
Guilford’s housing market reflects its rural charm. Historic 18th- and 19th-century farmhouses are scattered between mid-century ramblers, rustic log cabins, colonial-style homes and the occasional contemporary custom-built home. Most properties range between the low-$200,000s to the upper-$500,000s. A handful of properties with acreage can sell in the $800,000s, while small off-the-grid hideaways with no running water or electricity can sell for under $150,000. “In Vermont, we have first-home year-round communities and second-home resort communities,” Stephens says. “Guilford is a first-home community, but even our most rural towns offer a healthy mix of homegrown residents and transplants,” Stephens says.
Education interwoven with Guilford’s agricultural roots
The Windham Southeast Supervisory Union school district enrolls around 2,500 students across several school districts and five towns, including Guilford, Brattleboro, Dummerston, Putney and Vernon. Pre-kindergarteners through sixth graders may attend Guilford Central School, which earns a B-minus from Niche. Education here is deeply rooted in local values. The GCS Farm-to-School program aims to connect students with their agricultural roots while supporting the local economy. Activities range from gardening and farm field trips to cooking lessons and a school-wide composting program. The B-minus-rated Brattleboro Area Middle School serves grades seven and eight, and Brattleboro Union High School, which serves ninth through twelfth grades, earns a B-minus.
Small-town and city amenities
Local establishments line U.S. Route 5, including a small auto shop, a church and the Guilford Country Store. This community staple serves breakfast, lunch and fresh pastries made in-house, along with locally sourced jams, flowers and honey. Frequent events like wine tastings and open mic nights make it a popular gathering place for Guilford residents. Surrounding farms sell local products, such as homemade ice cream at Blueberry Haus, and fresh eggs, meats and authentic Vermont maple syrup at Franklin Farm.
Brattleboro offers access to larger supermarkets, restaurants, breweries and additional entertainment options. The city is about a 3-mile drive from the village center, or 15 miles from the farthest corner of town. “Brattleboro is the largest city in our area,” Stephens says. “So, you’re close to city entertainment, close to art, close to all the things, but can still enjoy rural living.”
Events and attractions in Guilford
The Guilford Fair, held every Labor Day Weekend, honors the region’s agricultural traditions with horse pulls, cattle shows, sheep shearing, homegrown exhibits and live music. Ten miles south, Gaines Farm, a family-owned operation for over 200 years, features a 7-acre corn maze in the fall along with a haunted hayride event called Vengeance in the Valley. Seven miles away, wedding parties and weekend warriors flock to Weatherhead Hollow, a private farmstead-turned-event venue and private artist residency that invites select creatives from around the country every year.
Getting around Guilford
Guilford is a car-dependent community, with most residents clustered along Guilford Center Road and Weatherhead Hollow Road. Brattleboro Memorial Hospital is about 3 miles north of Guilford’s main village center, which is situated at the intersection of Guilford Center Road and U.S. Route 5 on the northeast corner of town. Connecticut’s Bradley International Airport is the nearest international airport, about 80 miles south via Interstate 91.
