The Town of Chesterfield is a rural recreational hill town between Northampton and Pittsfield.  The town was laid out in 1739 and sites were granted to King Philip's and King William's war veterans in 1740, but initial settlement of the town did not take place until around 1755.

The town center was established after the Revolution with well preserved Federal Period houses along Main Road and landmarks of civic buildings in a later Greek Revival style. In its early days, the town supported a largely agricultural economy, with wool from Merino sheep as a major product.  However, there were sawmills and tanneries in operation as well as cloth dressing mills, and in the early 19th century these superseded farming and brought in a small immigrant population that was mostly Irish.

Progress wiped out most of the industry in Chesterfield and by the turn of the century a re-emerging agricultural economy developed alongside the growing trade from summer residents.