Lanesborough recreation attracts vacationers and new residents alike
It’s not uncommon for people to spend childhood vacations at Lanesborough’s ski slopes and apple farms, only to return to the small Massachusetts town as adults. For example, Lisa Wellspeak grew up visiting her cousins in Lanesborough, and she remembers summers of ponies, dirt bikes and blueberry picking at Mount Greylock. As an adult, she moved from Pittsfield to Lanesborough, where she’s now the town’s assessor clerk. The communities neighbor each other, but driving from Pittsfield to Lanesborough offers a stark change in landscape, as dense city streets give way to lakefront, trees and mountains. “When you leave Pittsfield and come into Lanesborough, it’s like you’re entering another world,” Wellspeak says. Other Lanesborough residents grew up much farther away, but similar fond memories of childhood vacations drew them back. The community is part of The Berkshires, a region of Western Massachusetts rich with outdoor activities. In addition, Lanesborough is in a well-regarded public school district that makes it desirable as a permanent home, not just a vacation spot.
Recreation from Mount Greylock in the north to Pontoosuc Lake to the south
Mount Greylock’s 3,500-foot summit rises on the north side of Lanesborough. Dozens of miles of trails, including a portion of the Appalachian Trail, wind around the mountain or lead to its peak, the highest point in the state. Many other hiking trails extend through Lanesborough, with several at Balance Rock State Park. Walking paths lead to the “Balance Rock,” a boulder that seems to defy physics by how it’s perched on a small stone. Boaters and paddlers are on the water at Pontoosuc Lake throughout the spring and summer, but fishers are also active in the winter, when ice fishing draws people from across Massachusetts. The 12-mile Ashuwillticook Rail Trail passes through the west end of Lanesborough, hugging the bank of the Cheshire Reservoir and connecting to nearby towns such as Adams. “You can see water, and you can see ducks and geese as you’re riding your bike,” Wellspeak says. Skiers head to Jiminy Peak Mountain Resort in the neighboring town of Hancock. Back in Lanesborough, Bill Laston Memorial Park hosts a playground and youth lacrosse, football and baseball games.
In the summer, the town holds Lanesborough Day at the park, bringing live music, free snacks and inflatables. In 2025, the community began putting on Winter Fun Fest, a mix of indoor and outdoor activities including live music, hot chocolate and a bonfire.
Homes among Western Massachusetts' lakefront and farmland
People from New York, North Carolina and even Florida have relocated to Lanesborough in recent years. Ranch homes and Cape Cods are concentrated around Pontoosuc Lake and in the middle of Lanesborough. These houses are typically lined up on lots of an acre or less. To the north, some farmhouses have been converted into country escapes with dozens of acres. Turnkey home prices typically vary from $200,000 to $500,000, while houses with four-plus bedrooms or a lakefront location can cost up to $1.1 million.
Well-rated schools in the Mount Greylock Regional School District
Before seventh grade, children can attend Lanesborough Elementary School. Mount Greylock Regional School is a combined middle and high school that teaches all other students in the district. Mount Greylock Regional School offers more than 15 Advanced Placement classes, allowing students to potentially earn college credits in physics, computer science and other topics. Niche gives both schools A-minus grades.
250 years of gathering at St. Luke’s
Founded in 1767, St. Luke’s Episcopal Church is the 11th-oldest Episcopal parish in the state. The congregation worships in a wooden church near the center of Lanesborough. From there, St. Luke’s collects and donates clothes and blankets, gathers in December for caroling and holds classes for the community, such as fraud prevention training for seniors.
Dining along Route 7, weekends in Williamstown
Lanesborough’s few stores and restaurants line U.S. Route 7. Coasters and awards cover the walls of Olde Forge Restaurant, known for its Buffalo wings and globe-spanning beer menu. People can make grocery runs to Target on the southeast side of town. People may go 15 miles north to visit Williamstown, home to Williams College and a collection of restaurants and shops. “It’s a cute little touristy town,” Wellspeak says. “They have football games, and those weekends are bustling with people.”
Cars, buses travel along Route 7
Locals generally rely on cars to get around, with Route 7 the primary highway through the community. Berkshire Regional Transit Authority buses stop along Route 7 on their way to and from Pittsfield. It’s 60 miles to Springfield, Western Massachusetts’ largest city.
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