Cheshire, MA


Cheshire: The AT follows a number of streets in the center of Cheshire for 0.6 miles. From the south, the trail comes out on Furnace Hill Rd. which it follows until it turns onto East Main St. From there, East Main continues onto Main St. and Church St. before turning onto School St. At the Senior Center, the AT leaves School St. but crosses MA Rte. 8 and Overlook Ave. before entering Mt. Greylock State Reservation. A hardware store is located on Church St. (off the trail) and the post office is at the intersection of Church and School streets. A Berkshire Regional Transit Authority bus stops at the post office and can provide transit to both North Adams and Pittsfield. A discount store and a convenience store with fast food options are close to the AT’s crossing at MA Rte. 8. In 2018, Cheshire achieved its Appalachian Trail Community designation.

Cheshire is smaller than either Dalton to the south or Adams to the north; however, it still has a number of businesses along both MA Rte. 8 and Church St. These include an inn and a restaurant on MA Rte. 8. A prominent feature is Cheshire Lake, south of downtown on Rte. 8. Cheshire is more or less the mid-point of the 11-mile-long Ashuwillticook Rail Trail which ends in Adams to the north and at the Pittsfield city line to the south.

Did you know? When Thomas Jefferson was elected president, the residents of Cheshire sent him a cheese weighing 1,235 lbs. in honor of his election. A replica of the cheese press that was used is on the AT near the intersection of Church and School streets.

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