Ashfield was first settled in 1743 and was officially incorporated in 1765. The town was originally called "Huntstown" for Captain Ephraim Hunt, who died in King William's War, and who had inherited the land as payment for his services. The first permanent settlement was in 1745, by Richard Ellis, an Irish immigrant from the town of Easton. The town was renamed upon reincorporation, although there is debate over its namesake; it is either for the ash trees in the area, or because Governor Bernard had friends in Ashfield, England. The town had a small peppermint industry in the nineteenth century, but for the most part the town has had a mostly agrarian economy, with some tourism around Ashfield Pond.

Ashfield is the birthplace of prominent director Cecil B. DeMille (whose parents were vacationing in the town at the time), Alvan Clark, nineteenth century astronomer and telescope maker, and William S. Clark, member of the Massachusetts Senate and third president of Massachusetts Agricultural College (now UMass Amherst).

According to the United States Census Bureau, the town has a total area of 40.3 square miles (104.3 km²), of which 40.0 square miles (103.6 km²) is land and 0.27 square miles (0.7 km²), or 0.62%, is water. Ashfield is located in the southwest corner of Franklin County, along the Hampshire County line. Ashfield is bordered by Buckland to the north, Conway to the east, Goshen to the south, Cummington to the southwest, Plainfield to the west, and Hawley to the northwest. Ashfield is 15 miles (24 km) west-southwest of Greenfield, 35 miles (56 km) north-northwest of Springfield, and 105 miles (169 km) west-northwest of Boston.

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