Dummerston offers a quiet, rural lifestyle with a natural landscape
In the rural outskirts of southern Vermont, Dummerston offers a small-town atmosphere and an outdoorsy lifestyle. “The city folk have found us, so we’ve become more desirable,” says Christine Lewis, a local broker at Brattleboro Area Realty. “We have hills and valleys, which give us nice views and waterways. The town is laid out with nature preserves all around us, so we attract an active crowd.” The quiet Windham County area is home to less than 2,000 residents, but what it lacks in population it makes up for in historical landmarks and nature trails. The Connecticut River runs along the area’s east side, and the West River flows through the center of town, both waterways providing additional summertime recreation. Residents often hop over to the neighboring Brattleboro for fine dining and entertainment, and Interstate 91 helps to connect commuters to the rest of New England.
Nature lovers can visit historic bridges, trails and campgrounds
Outdoors enthusiasts can choose from several hiking trails throughout town, some marked with small parking lots near the trail’s entrances and some hidden but locally known. At Old Jelly Mill Falls, visitors can hike a short distance to the cascading waterfall or to the calmer part of the river for floating and toe-dipping. On-site, Rice Farm Road Bridge is one of the state’s oldest iron truss bridges, built in 1892. It was listed on the National Register of Historic Places in 1995. About a mile north along the river, the Historic Dummerston Covered Bridge is the longest in the state at 280 feet. Part of Vermont’s covered bridge tour, the landmark was listed on the National Register of Historic Places in 1973.
On the east side of town, Dutton Pines State Park provides protected land with a short hiking loop. Nearby, Kampfires is an RV park and campground with an outdoor pool, ice cream stand, mini golf and a lineup of events. The park hosts a free Friday night concert series from May through the end of August, as well as Baconfest and The New England Street Food Festival in the fall.
Dummerston features vintage cottages and contemporaries
The primarily residential and rural town has a low housing inventory, and it’s common for only one or two homes to be on the market at any given time. Buyers can find 700- to 2,000-square-foot cottage-style bungalows and Colonial Revivals tucked in the woods, many with detached garages. While some properties, typically those built between the 1950s and 1980s, may need updates, others have seen recent renovations. Price tags range from $290,000 for a home on a half-acre to $325,000 for a house on about three acres. Larger homes with contemporary architecture that plays on rambling ranch-styles or farmhouse styles might have eclectic touches like colorful facades. These 2,000- to 7,000-square-foot contemporaries usually sit on 10 to 39 acres, with private ponds and shielded by forested landscapes. Many of these homes boast vintage pieces from their original build date, as early as 1776 in some instances, while newer 2000s builds feature multi-level wrap-around balconies. Prices for these larger homes typically range from $635,000 to $965,000, although there are custom-built farmhouse outliers for upwards of $3 million.
Brattleboro offers niche country markets and local eateries
While shopping and dining is limited in Dummerston, the neighboring town of Brattleboro is teeming with local eateries and boutiques. The Vermont Country Deli is a popular roadside market with woodsy, old-timey decor that prepares made-to-order sandwiches and fresh baked goods alongside niche gifts like maple syrup, books and kitchenware. “Brattleboro has a lot of quality restaurants, a few 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.” T.J. Buckley’s offers an upscale seasonal menu in a refurbished train car, and Kipling’s Tavern, named after the famous author who was a former resident, is an Irish pub. For groceries, there’s Hannaford.
Dummerston’s apple pie fest and Brattleboro's art walk
Crowds flock to Dummerston each October for the Dummerston Apple Pie Festival, when the leaves turn red and orange and apples are at their ripest. The event, which is celebrating its 55th year in 2025, features pies, cider donuts, cheeses and ice cream. “The Vermont Theater Company also performs at the Evening Star Grange, which is in Dummerston,” Lewis says. The company and its players are popular for their one-act plays.
Residents can head to Brattleboro to listen to live music or peruse the town’s many art galleries. “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."
Guests can stay at author Kipling’s historic Naulakha house
Rudyard Kipling wrote “The Jungle Book” while living at the southern end of Dummerston. Kipling and his wife, a Brattleboro native, built and settled in a shingle-style home they called Naulakha in 1892. About a century later, the house became a National Historic Landmark and has been restored as a tourist retreat, where visitors can spend the night or host an event.
Students are served by the Windham Southeast Supervisory Union
The Windham Southeast Supervisory Union, which receives a C-plus rating from Niche, serves students living in Dummerston. Learners can begin at Dummerston School, a kindergarten through eighth-grade school with a B rating. They can then advance to Brattleboro Union High School, which receives a B-minus and partners with the Windham Regional Career Center to offer students three academies: STEM, Visual Performing Arts and International Studies.
Commuters can access Springfield and Hartford via Interstate 91
Interstate 91 and U.S. Route 5 run parallel along Dummerston's east side, connecting residents to surrounding Windham County towns. Springfield, Massachusetts, is about a 65-mile commute south on the interstate, and Hartford, Connecticut, is 25 more miles past there. Residents typically fly out of Bradley International Airport, located about 85 miles south. “Most people use Bradley in Connecticut because it’s easier to get to,” Lewis says. “But some choose Boston or New York if they’re flying internationally.” There is no public bus service in Dummerston, but residents can catch the MOOver shuttle at the southernmost end of town off Route 5. The free Southern Vermont bus services the rest of Windham County.
Written By
Mary Beth Greene
