An artsy, outdoorsy Massachusetts Hilltown
Cummington is one of 28 rural Hilltowns in Western Massachusetts. “Part of the appeal is that it’s a small, very close-knit town, but very accepting of others. And we’re the smallest town in Massachusetts to have our own Cultural District, so a lot of artists and writers live here,” says Carla Ness, a co-owner of Delap Real Estate with three decades of experience working with clients in the area. As the birthplace of 19th-century poet William Cullen Bryant and home of The Cummington Press, which published special editions of works by 20th-century poets, Cummington has long been a haven for artists. “You get to live in this beautiful, peaceful environment, surrounded by nature, but you’re not in nowhere land culturally, so that’s quite nice,” Ness says.
Classic New England Colonials, farmhouses and cottages
Colonials, farmhouses and Cape Cod cottages are common, and most sit on spacious properties. “A lot of people who move here are interested in farming activities or homesteading, sometimes commercially, but more often not. It’s a lot of people who are just interested in being outside,” Ness says. Land prices start close to $40,000 and rise to about $70,000. Home prices range between $150,000 and $625,000, though historic farmhouses with barns and dozens of acres can go for over $1 million.
Central Berkshire Regional School District and J.S. Bryant School
Cummington is zoned to the Central Berkshire Regional School District. The small system serves just over 1,500 students across three elementary schools, one middle and one high school. School choice is available, but most Cummington students attend Kittredge Elementary, which receives an A from Niche. Older students continue to Nessacus Regional Middle, which gets a B-minus, and Wahconah Regional High, which gets a B. The current campus opened in 2021 following a $72 million building project. J.S. Bryant School is a private, not-for-profit LGBTQIA+ therapeutic high school. Opening in the fall of 2025, J.S. Bryant School doesn’t yet have a Niche grade.
Hilltown history museums and winter outdoor recreation
The Kingman Tavern Museum, in the middle of town, displays over 5,000 artifacts showing 200 years of farming, industrial and domestic life in Cummington. “It’s a world-class history museum, really super fabulous," Ness says. The William Cullen Bryant Homestead, a 195-acre property with a three-story Victorian cottage, is nearby, not far from Bryant Mountain State Forest. While the house is currently closed for tours, the grounds are open to the public. The woods beyond are popular for backcountry skiing and snowboarding. The Windsor, Chesterfield Gorge and Gilbert A. Bliss state forests feature miles of hiking trails, all within a 10-mile radius.
Regular events at the Cummington Fairgrounds and the Village Church
The fairgrounds to the south host the annual Cummington Fair in August, with livestock shows, truck pulls, a lumberjack competition and kids’ games. “Other things happen there, too, like the Sheep & Woolcraft Fair on Memorial Day weekend, the Renaissance Fair in August, typical 4-H events, tractor fairs, that kind of thing,” Ness says. The Cummington Cultural Council’s biweekly Friday Night Café brings the town together for poetry readings, live music and more between September and June. They’re held in the Village Church, on Main Street, an interfaith congregational church established in the 1830s.
Limited shopping/dining in Cummington, more options in Williamsburg
The shopping and dining scene in Cummington is limited to the small collection of businesses on Main Street. Cummington Supply, the local hardware store, is across from the post office. Project Art, down the way, is a contemporary ceramics studio. The renovated 19th-century mill building hosts artist residencies, private classes and workshops. Ferrin Contemporary is the adjacent gallery, open by appointment. “Cummington Creamery is the real heart of the town,” Ness says, referring to Old Creamery Co-Op. The shop has conventional groceries, as well as locally grown produce and locally sourced meat, seafood and dairy products. “There are also a ton of great farms with farm stands in the area,” Ness says. Historic downtown Williamsburg, about 13 miles away, has more shopping and dining options.
Car-dependent rural Massachusetts
Massachusetts Route 9 runs diagonally through Cummington, connecting northwest to Windsor and southeast toward Northampton. Parts of Massachusetts Route 112, a north-south highway, are concurrent with Route 9. The Franklin Regional Transit Authority provides paratransit service to the area, but no fixed-route bus service is available. The closest Amtrak train stations are in Pittsfield and Northampton, over 20 miles away.
