The valley town was founded by Baptists from Rhode Island, the first settlers in the region who were not of the established Puritan Church. The early colonists were mostly descendants of those who had followed Roger Williams to Rhode Island to practice freely. One of the emigration's leaders was Colonel Joab Stafford, who built his house on Stafford Hill and led the men of Cheshire into war during the Revolution. The troops from Cheshire distinguished themselves at the Battle of Bennington in 1777.

Cheshire was incorporated in 1793, and its residents were strongly partisan in the election battles of the country's early days. The Adams–Jefferson election of 1800 was hard fought, and Cheshire was the only Berkshire town that favored Jefferson. When their candidate won the election, the town searched for a way to show their support and pay a tribute to their new president. Because Cheshire, like their namesake, specialized in dairying and making cheese, they decided to send a gift to the president of a Cheshire cheese that used curds from every farmer in town. The resulting cheese was 4 feet (1.2 m) in diameter, 18 inches (460 mm) thick and weighed 1,235 pounds (560 kg). It was moved on a sled drawn by six horses when it was shipped off to Washington, D.C. by water, where it drew a personal letter of thanks from President Jefferson. One of the two monuments in Cheshire commemorates the cheese; the other memorializes the founders of the town. The Pioneer Monument is on Stafford Hill and is a fieldstone replica of Benedict Arnold's Norse Mill in Newport, Rhode Island. The view from the monument is arguably one of the most beautiful views in the Berkshires.

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