$395,745Average Value$255Average Price per Sq Ft7Homes For Sale
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 Western 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.
Lanesborough's history and town pride is on display with a unique quote from Josh Billings.
Outdoor recreation is a huge draw for Lanesborough with scenic views of the water and mountains.
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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.
The Cheshire Reservoir is a popular spot for kayaking and is a short drive from Lanesborough.
The Ashuwillticook Rail Trail stretches through the Eastern part of Lanesborough and is popular for casual strolls or more serious hikes.
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Homes among Western Massachusetts' lakefront and farmland
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.
People from New York, North Carolina and even Florida have relocated to Lanesborough in recent years. That trend picked up after the onset of the COVID-19 pandemic sent many people searching for homes in more remote areas, says Barb Hassan, owner of Barb Hassan Realty in Lanesborough. "During COVID, many people from the cities made this their second home," she says. "But after COVID, many people stayed." Tourists also frequent Lanesborough, but Hassan says it's not an influx of crowds that disrupts the community. "Our summer season is when we see the most people coming back to the lake communities."
Larger homes tucked off the street are popular with home buyers in the Lanesborough area.
Many homes within the Lanesborough area sit on the edge of heavily forested areas.
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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.
Lanesborough Elementary School has an overall grade of A- on Niche.
Greylock Regional High School is an academic springboard for students of Williamstown.
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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. Some people buy from local farms like Red Shirt Farm, where people can pay a fee to receive a cut of what the farms grows and raises. "There are plenty of them, where you can go and pick up fresh-grown food, get eggs and order turkeys," Hassan says. 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.”
Olde Forge Restaurant is a local favorite for pub food and it's iconic salad bar.
Residents of Lanesborough don't have to travel too far into Pittsfield to pick up staples from big box stores like Target.
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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.
Written By
Alex Soderstrom
Photography Contributed By
Noel Poage
Video By
Becky Gaskill
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GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Lanesborough, MA sell after 56 days on the market compared to the national average of 49 days. The median sale price for homes in Lanesborough, MA over the last 12 months is $280,000, down 13% from the median home sale price over the previous 12 months.
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