Cheshire, Massachusetts
A Short History of Cheshire
From a Baptist farming settlement in the northern Berkshires, to the town that made a 1,235 pound cheese for a president, Cheshire has spent more than two centuries deciding its own affairs in one room.
A Baptist Town in the Hills
Cheshire was first settled in the late 1760s and incorporated as a town in 1793, taking its name from Cheshire in England. Many of its first families were Baptists who had come from Rhode Island and southeastern Massachusetts, and their faith shaped the town’s character early. Joab Stafford, one of the first settlers, helped win the Battle of Bennington in the Revolution, and a stone tower on Stafford Hill marks his burial site. From the start this was a farming town, and its cows would soon make it briefly famous.
The Mammoth Cheese
When Thomas Jefferson won the presidency, Elder John Leland, the town’s Baptist minister, who had lived in Virginia and knew Jefferson, persuaded the farmers of Cheshire to pool a full day’s worth of curds into one enormous cheese. The Cheshire Mammoth Cheese weighed 1,235 pounds. After a hard journey of a month, it was presented to President Jefferson at the White House on New Year’s Day of 1802. It was a small hill town making itself heard at the very top of the new republic, and it is still the story Cheshire tells about itself.
Forges, Mills, and Glass
Through the nineteenth century Cheshire’s economy ran on water power and local resources. The town had early forges and saw mills, grist mills, and tanneries, and the Cheshire Crown Glass factory was the first glass works in the Berkshires. Farming, and especially dairy, remained the backbone of the town, and the lime and iron of the Berkshires gave it small industry alongside the fields.
Mountains, Water, and a Rail Trail
Cheshire sits in a dramatic corner of the state, near Mount Greylock, the highest point in Massachusetts, with the Hoosic River valley running through it. The Appalachian Trail winds through the center of town on its way to the summit of Greylock. Today the Ashuwillticook Rail Trail, built on the old rail bed, runs along the shore of the Cheshire Reservoir and through the center of town before following the Hoosic River into Adams, carrying walkers and cyclists past the same fields that once fed a president’s cheese.
MassCivics last checked this page on September 26, 2026.
Sources
- Town records: Town of Cheshire, About, History, written by Barry Emery, as of September 23, 2026.