The valley town was founded by Baptists from Rhode Island, the first settlers in the region who were not of the established Puritan Church.

When their candidate won the election, the town searched for a way to show their support and pay a tribute to their new president.

The resulting cheese was 4 feet (1.2 m) in diameter, 18 inches (460 mm) thick and weighed 1,235 pounds (560 kg).

It was moved on a sled drawn by six horses when it was shipped off to Washington, D.C. by water, where it drew a personal letter of thanks from President Jefferson.

The Pioneer Monument is on Stafford Hill and is a fieldstone replica of Benedict Arnold's Norse Mill in Newport, Rhode Island.

His son, Thomas J. Curtin, Jr., owned and operated a silica sand quarry and mill located on the East side of Hoosac Lake (formerly known as the Cheshire Reservoir).

The rural town has been taking on recreational and residential overtones in modern times, with 225 acres (91 ha) of open slopes and wooded trails for skiers on Farnhams.

In addition, there has been good fishing in the South Branch of the Hoosic River, which originates in Hoosac Lake in the town.

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.

Cheshire is bounded 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.

Route 116 also cuts through the northeast corner of town, and several sections provide panoramic views of Mount Greylock to the west.

Most of the line was converted into the Ashuwillticook Rail Trail /ˌæʃuːˈwɪltɪkʊk/, an 11-mile (18 km)-long, 10-foot-wide (3.0 m), universally accessible, paved path connecting the Berkshire towns of Lanesborough, Cheshire, and Adams.

Cheshire Reservoir, the Hoosic River and associated wetland communities flank much of the trail, offering outstanding views and abundant wildlife.

Cheshire employs the open town meeting form of government, and is led by a board of selectmen.

The town is roughly located equidistantly between the North Adams Regional Hospital and Berkshire Medical Center in Pittsfield.