The area named New Providence was settled in the late 1760s.  Most of the original inhabitants were Baptists who had moved from Rhode Island and southeastern Massachusetts.  They were farmers and the land was similar to its namesake, Cheshire in England.  Successful dairy farming developed and cheese was one of the area’s greatest products.  After seventeen years  and several requests to state government, a township was formed on March 14, 1793.  New Providence  along with parts of New Ashford, Lanesborough, and Windsor were incorporated as Cheshire.

Joab Stafford was one of New Providence’s settlers and his exploits along with those of the other patriots helped to win the Battle of Bennington during the War of Independence.  A monument in town erected on Stafford Hill (formerly New Providence Hill) serves as Stafford’s burial site and commemorates their contributions during the war.  The monument, a stone tower, is a replica of one in New Port, RI. and the site affords a beautiful scenic view.

Elder John Leland was the town’s Baptist minister in 1800 during the election between Jefferson and John Adams of Massachusetts.  When Jefferson was elected president, Leland, who had lived in Virginia and knew Jefferson, influenced the farmers into contributing a full day’s worth of curds to make a ‘Mammoth Cheese’ weighing 1235 pounds. After an arduous journey of a month, it was presented to President  Jefferson at the White House on January 1, 1802.  A full size monument of the cheese press and a replica of the cheese itself has been placed in the center of town across from the post office.  Elder Leland is also famous for his friendship with James Madison and it was Leland who convinced Madison there needed to be greater guarantees of personal freedoms in our constitution.  This belief  led Madison to  propose the amendments known as the Bill of Rights.

Abundant streams for water power led to early forges and saw mills, grist mills and tanneries. The Cheshire Crown Glass factory was the first in the Berkshires but its operation along with other glass making was short lived.  However, one factory circa 1854 made the first piece of plate glass in America. 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.

When railroad service reached Cheshire in 1846, it fostered a transformation that saw the growth of a variety of new industries along with the continued production of cheese.  The tonnage shipped from town included raw lumber, lime, iron, and sand for making glass and fire bricks.  During the last half of the nineteenth century the pure quartz sand was considered the best available in the country and it was shipped to glass factories in the United States and elsewhere. The Farnam brothers, after returning from the civil war, started a lime factory in the southern section of Cheshire.  The lime company became very prosperous and after many expansions that part of town became known as Farnams. In the same area a small brook was dammed to produce a reliable water supply for companies downstream in Adams. The lime company is gone but the reservoir continues as a popular boating and fishing venue.

As with most industries in northern Berkshire, the local factories eventually closed or moved to other communities.  When rail traffic ended the rail bed was turned into a beautiful walking/bike trail called the Ashuwillticook.  The trail runs along the shore of the reservoir and through the center of town before following the Hoosic River into Adams.  America’s most famous hiking path, the Appalachian Trail, also winds its way through the center of town before heading up to the summit of Mt. Greylock.  The trails and the scenic beauty of the town continue to be valuable assets, attracting many visitors and new homeowners.

Cheshire continues to grow in community spirit and pride.  Events such as Cruz Night with fireworks, summer block parties, community clean-up events, memorial day parades, and church functions  bring people together.

Town historian Barry Emery has given annual slide presentations on a variety of topics and his talks have been recorded and uploaded to YouTube. If you are interested in discovering more about Cheshire’s past you can watch these historical videos at youtube.com/user/emery395

In 1792 Elder John Leland, a Baptist preacher, had moved to Cheshire after spending over a decade living and preaching in Virginia.  While there he became very involved with a crusade to guarantee religious freedom and the separation of religion from government.  Leland knew and became  friends with several major political figures living near his Orange County home, including James Madison and Thomas Jefferson.  Those men were intimately involved in the formation of our country and the documents defining our nation.

When Jefferson was elected president in 1801, Leland wanted to mark the occasion in a spectacular way, considering Cheshire had voted unanimously for Jefferson.  An idea was devised for a spectacular gift that would allow everyone in town to participate in its creation - the making of a giant cheese.

On the appointed day in July (1801), town's folk brought their production of curds to Capt. Daniel Brown's cider mill where they were pressed into an enormous cheese weighing over half a ton.  When the huge cheese had cured it was taken to Washington, DC by Elder John Leland and Darius Brown.  Brown was the son of Cheshire's most prominent citizen, Captain Daniel Brown.

On New Year's Day of 1802, the Mammoth Cheese, weighing 1235 pounds, was presented to President Jefferson in a formal ceremony at the president's mansion (now called the Whitehouse).  Speeches were given by Leland and Jefferson and members of Jefferson's cabinet where on hand to witness the event.

Former Masonic meeting place replete with an eight panel Christian door which forms the double cross as protection from witchcraft.

Beneath the wallpaper in one of the rooms was discovered the beehive, the Royal Arch, the Bible - balance, the square and the compass.

The bridge over Bassett Brook was built in 1830. The original bridge was added to in 1902 to accomodate a trolley line from Adams to Cheshire.