Along the western border, Berkshire County, M.A. has a population count of 129,026 and spans across 946 miles of the state. This county is home to larger cities like Pittsfield, which is the county seat, North Adams, and Great Barrington. This area also encompasses plenty of parks and reservations like October Mountain State Forest and Mt. Washington State Forest.

Cheshire is located within the valley of the Hoosic River, and is the site of a dammed reservoir on the river. To the west, parts of Mount Greylock State Reservation take up sections of town, and includes a section of the auto road. To the southeast, North Mountain peaks just outside town limits before descending to the valley. The Appalachian Trail crosses through the center of town, heading from North Mountain to Mount Greylock. The spectacular Berkshire countryside provides numerous trails and back roads for hiking, cycling, bird watching, cross country skiing and snowshoeing. Read more about the area and the nearby town of Lee and the town of Great Barrington in our town guides.