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Cheshire Colonel Joab Stafford, a man who distinguished himself in America's fight for independence, is also credited for having won Cheshire's independence, albeit in a much more peaceful way.
Before Stafford entered the picture, however, Cheshire's history was set forth by Nicholas Cook and Joseph Bennett, investors from Rhode island. In 1766, the two purchased a territory then known as North Berkshire Township Number 6. The territory was later divided into tracts that would ultimately make up parts of not only Cheshire, but also Savoy, Lanesborough, and the original township of Adams.
Cook and Bennett hired Stafford to survey their holdings and ultimately agreed to sell him 396 acres of rolling hills. An equally enterprising Stafford then convened a group of families (Low, Wells, Brown, Carpenter, Jenkes, Mason, Bliss, Tibbets, and Cowmans) to help him settle his new acquisition, a parcel of land they named New Providence. The residents of Cheshire later renamed the area Stafford Hill in deference to their founding father.
The Stafford Hill Monument, erected in 1927, also pays tribute to the colonel. Created by the Massachusetts Sons of the American Revolution, the graveside monument acknowledges Stafford's heroic role in the Battle of Bennington fought in 1777.
Nearly a generation later, in 1793, the territory in and around Stafford Hill incorporated into Cheshire. It was not until 1801, though, that Cheshire put itself on the map metaphorically. That's when Cheshire resident John LeLand, a preacher and national political pooh-bah, received nationwide attention for presenting President Thomas Jefferson a 1,450-pound cheese.
LeLand shipped the cheese to Washington after transporting it to the Hudson River via a team of oxen. A replica of the original cheese press presented to Jefferson as a "Token of Regard from the Citizens of Cheshire" now sits in Cheshire's Leland Park.
During the early 19th century, Cheshire's population gradually shifted toward the present-day town center to use available water power from the Hoosic River.
The Berkshire Iron Furnace, Dean Saw Mill, and the Cheshire Shoe Factory helped boost Cheshire's economic development, as did the Crown Glass Company, which is on record as having employed the most residents back then. In fact, some of the earliest plate glass in Massachusetts traces back to Cheshire, and after the town moved on to other industrial pursuits, it continued to import its high-quality sand to glass-makers throughout the state.
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