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there were sawmills and tanneries in operation as well as cloth dressing mills, and in the early 19th century these superseded farming and brought in a small immigrant population that was mostly Irish.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.

Chesterfield Massachusetts is located in 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.

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