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. Cheshire's town center is located northeast of Pittsfield, northwest of Springfield, and west-northwest of Boston (although the town is closer to Hartford and Albany than its own state capital).
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. Cheshire's town center is located northeast of Pittsfield, northwest of Springfield, and west-northwest of Boston (although the town is closer to Hartford and A.lbany than its own state capital).