$381,853Average Value$197Average Price per Sq Ft12Homes For Sale
Small-town living in mountainous Massachusetts
Cheshire is a small town near Pittsfield in the mountainous Berkshires region of northwestern Massachusetts. Settled in the 1700s as a dairy farming community, its claim to fame is a “Mammoth Cheese” weighing 1,235 pounds, made by Baptist minister John Leland to celebrate his friend Thomas Jefferson’s victory in the 1800 presidential election. An almost life-sized replica stands in the center of town today. Cheshire’s big cheese may be iconic, but it’s not why people move here. “It’s very small, very quaint. This area is known for outdoor recreation, specifically hiking. If you live here, you really are one with nature, and the cell phone service is questionable at best,” says Nathan Girard, a Royal Properties Group Realtor with over a decade of experience working with clients in the area.
Kayakers can enjoy endless views of nature at the Cheshire Reservoir.
The Berkshire mountains are a mere stones throw away from the scenic and quaint town of Cheshire.
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Northern Berkshires hiking and camping
The nearly 13-mile Ashuwillticook Rail Trail loosely follows the Hoosic River and Cheshire Reservoir, connecting the neighboring towns of Lanesborough and Adams. The 10-foot-wide paved path is open year-round for walking, biking, cross-country skiing and snowshoeing. A section of the Appalachian Trail also runs through town. Mount Greylock, the highest point in Massachusetts, is about an 8-mile hike north. The Cobbles is a shorter, southbound A.T. hike with views of the Taconic Mountains and the reservoir. Father Tom Campsite, named after an avid local hiker and former pastor of St. Mary’s Church, is a popular stop for thru-hikers. The small campground also hosts the Cheshire Community Association’s annual Appalachian Trail Community Celebration Day, with live music, food and guided hikes. Cheshire Town Hall houses the local library and youth center. A public playground and baseball field are right outside, and the Cheshire Senior Center is less than a mile down the road. Regular town events include summer block parties, community clean-ups and the annual Memorial Day parade.
The Ashuwillticook Rail Trail runs throughout the Cheshire area and is a great way to get around town.
The Appalachian Trail is easily accessible and has several markers throughout the Cheshire area.
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Competitive prices for classic New England homes
Farmhouses and Colonial Revivals built between the late 1800s and early 1900s are common, as are midcentury brick ranch-style homes, split-levels and Cape Cods. Prices start close to $210,000 and climb to about $600,000, still lower than the state median. “People want to live here because the taxes are very low and because you can get a lakefront, 3,000-square-foot home with a dock for $500,000 or a standard 1,500-square-foot Cape or ranch for $350,000,” Girard says.
Ranch style homes sit on spacious lots within the scenic Cheshire neighborhood.
Cape Cod style homes will catch your eye as you drive around the beautiful Cheshire area.
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Hoosac Valley Regional Schools serve Cheshire
The Hoosac Valley Regional School District serves the Cheshire and Adams communities. The small system comprises three schools: Hoosac Valley Elementary, Hoosac Valley Middle and Hoosac Valley High. Each gets a C-plus grade from Niche. The high school, which shares a campus with the middle school, offers Innovations Pathway programs in sports medicine, education and environmental studies, among others.
Hoosac Valley Middle & High School has an overall grade of C+ on Niche.
Hoosac Valley Middle School has an overall grade of C+ on Niche.
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Limited shopping/dining in Cheshire
Dollar General, which opened in 2017, is Cheshire’s only chain retailer. It’s close to Harry’s Auto, a small used car dealership and servicing shop. The Shell station down the road has a Dunkin’, the only chain restaurant. Other shopping options include Cheshire Liquor Center and B&W Firearms, a family-owned gunsmith, accessories and supplies shop. Cheshire Glassworks is an art studio and gallery near Common Table, an American eatery opened in 2024. “It’s a popular little gathering spot. They’re busy every night. So busy that I’ve tried to go a couple times and they couldn’t accommodate a reservation,” Girard says. For a wider variety of shopping and dining, residents head into Pittsfield. Whitney’s Farm Market & Garden Center, between Cheshire and the neighboring city, sells seasonal, locally sourced produce and plants.
Residents of Cheshire don't have to travel far to get pantry staples at the local Dollar General.
Common Table in Cheshire is a great spot to have a meal on the patio or in their intimate dining room.
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Massachusetts Route 8 runs to Pittsfield and Adams
Massachusetts Route 8 heads north through Adams and North Adams on its way toward Vermont, only 15 miles away. The two-lane highway also heads about 10 miles south into Pittsfield. Berkshire Medical Center, in north Pittsfield, is within a 20-minute drive of Cheshire. The closest international airport is in Albany, New York, about 50 miles northwest. Without traffic, it’s about an hour-long drive.
Written By
Megan Quintin
Photography Contributed By
Noel Poage
Video By
Adam Lapallo
Interested in learning more about homes in this area?
Reach out to
Kolleen Schmitt,
an experienced agent in this area.
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On average, homes in Cheshire, MA sell after 44 days on the market compared to the national average of 52 days. The median sale price for homes in Cheshire, MA over the last 12 months is $367,050, up 11% from the median home sale price over the previous 12 months.
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