The Elder John LeLand, first and foremost a preacher and later a national political figure, made and presented President Thomas Jefferson with a 1,450 pound cheese in 1801. A replica of the original cheese press now sits in Leland Park. The cheese was drawn by oxen to the Hudson River and shipped to Washington from there. It was presented to Jefferson as a "Token of Regard from the Citizens of Cheshire".

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.