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 southern foothills of the Hoosac Range make up much of the eastern side of town, and much of the land is dotted with sections of the Chalet and Stafford Hill Wildlife Management Areas. Several other brooks feed into the river along the way.