Like several towns throughout New England, Chesterfield started as a land grant community created for the heirs of soldiers who fought in the Narragansett War of 1675, otherwise known as King Philip's War. Chesterfield came into being in 1762. However, its borders remained in flux until 1810. A disputed area of land -- once separate, then part of Chesterfield, then separate again -- was incorporated as the town of Goshen in 1781. In the aftermath of that split-up, statues again changed the borders of both Chesterfield and Goshen, then three lots of Goshen's land were set back to Chesterfield. The transfer of land from the town of Williamsburg to both Chesterfield and Goshen finalized today's strange, jagged border of Chesterfield.

This is home to the Burkeville Covered Bridge, commonly referred to as the Conway Covered Bridge. The bridge is one of only three or four surviving 19th-century bridges of its kind in Massachusetts.

Built in 1871, the bridge has been closed to both automobiles since the 1980's and to foot traffic not long after. Local preservationists are currently seeking funding to restore and re-fortify the bridge to the extent that pedestrians can once again traverse its wooden slats.