Cheshire was incorporated in 1793, and its residents were strongly partisan in the election battles of the country's early days. The election campaign which put Thomas Jefferson into the presidency was hard fought and Cheshire was the only Berkshire town which 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, but one using curds from every farmer in town. The resulting huge cheese was four feet in diameter, 18 inches 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 field stone 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.
The town had early forges and saw mills, grist mills and tanneries, and in 1812, the Cheshire Crown Glass factory opened as did a triphammer operation. The town also boasted the first factory in western Massachusetts to manufacture cotton making machinery. Daniel Brown put 14 water looms into his cotton factory in 1827 and the making of shoes, cotton fabric and cheese were the mainstays of the town's 19th century economy.
The town's reputation for religious diversity continued, and in 1885 there were only 1,537 people in Cheshire but there were four different churches.
The rural town has been taking on recreational and residential overtones in modern times, with 225 acres (911,000 m²) of open slopes and wooded trails for skiers on Farnhams. There was in the 1940s a three-quarter of a mile (1.2 km) straight run at the Cheshire skiing area. In addition, there has been good fishing in the South Branch of the Hoosic, which originates in Hoosac Lake in the town. [cc]