[3] The town center, established after the Revolution, has well-preserved Federal period houses along Main Road.

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there were sawmills and tanneries in operation as well as cloth dressing mills, and in the early 19th century these superseded farming and brought in a small immigrant population that was mostly Irish.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 start of the 20th century a re-emerging agricultural economy developed alongside the growing trade from summer residents.

[4] Chesterfield's location is nearly equidistant from the northern, southern and western state lines of Massachusetts.

Chesterfield is part of the Hampshire Regional School District along with Goshen, Southampton, Westhampton, and Williamsburg.