Chesterfield, Massachusetts is located West central Massachusetts, bordered by Worthington on the west, Huntington and Westhampton on the south and southeast, Williamsburg on the east, Goshen on the northeast, and Cummington on the north. Chesterfield is 28 miles east of Pittsfield and 108 miles west of Boston. The principal highway is State Route 143, which connects up with the cross-state Worcester Turnpike (State Route 9) in the neighboring town of Williamsburg. There is no passenger or freight rail service in Chestefield, but the network of intermodal facilities serving Massachusetts is easily accessible.

Some information gathered on Chesterfield, MA is courtesy of Commonwealth Communities at Mass.gov