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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.

According to the United States Census Bureau, the town has a total area of 27.5 square miles (71.4 km²), of which, 26.9 square miles (69.8 km²) of it is land and 0.6 square miles (1.6 km²) of it (2.21%) is water.

Cheshire is bound by New Ashford to the northwest, Adams to the north, Savoy to the northeast, Windsor to the east, Dalton to the southeast, and Lanesborough to the south and west. Cheshire's town center is located 10.5 miles northeast of Pittsfield, 53 miles northwest of Springfield, and 135 miles west-northwest of Boston (although the town is closer to Hartford and Albany than its own state capital).

Massachusetts Route 8 is the main route through town, crossing from south to north. It was once part of New England Interstate Route 8, which led from North Adams to Bridgeport, Connecticut. Route 116 also cuts through the northeast corner of town, and several sections provide panoramic views of Mount Greylock to the west.

The town lies along one of the routes of the Berkshire Regional Transit Authority bus line. Regional service can be found in both North Adams and Pittsfield, as can regional air service. The nearest airport with national service is Albany International Airport.

The town is the site of an abandoned rail line. The Ashuwillticook Rail Trail is a scenic, paved, 11 mile (18 km) path connecting the Berkshire towns of Lanesboro, Cheshire, and Adams. The trail runs parallel to Route 8 and passes through woods and marshlands, and alongside a lake and a river, with wooded hills and Mt. Greylock, as a backdrop. The Trail is a former railroad corridor converted into a 10 foot (3 m) wide paved universally accessible path and has become a popular resource for biking, walking, roller-blading, jogging, etc. The southern end of the Trail begins at the entrance to the Berkshire Mall off Route 8 in Lanesborough and travels 11 miles north to the center of Adams. The Trial passes through the Hoosac River Valley, between Mount Greylock and the Hoosac Range. Cheshire Reservoir, the Hoosac River and associated wetland communities flank much of the trail offering outstanding views and abundant wildlife. The word Ashuwillticook is from the Native American name for the south branch of the Hoosic River and literally means “at the in-between pleasant river,” or in common tongue, “the pleasant river in between the hills.” The name was adopted for the trail as a way to reconnect people to local history and the natural environment. [cc]