Charlemont was first settled by Moses Rice (1694-1755) who purchased 2,200 acres (8.9 km²) on 23 April 1743 that been previously set off as Boston Township Number 1 in 1735 by the Great and General Court. The town was along the distant frontier at the time, and was the subject of several raids by Native Americans. While plowing in the fields one day, Rice was shot and wounded by Indians lying in ambush. They also shot and killed another man, Phineas Arms, at the same time and captured Moses' eight-year-old grandson Asa, who had been riding the plow horse. Moses was taken to the adjoining woods, scalped, and left for dead, but Asa was carried off to Canada. The town was incorporated as Charlemont in 1765, most likely named for the town in Northern Ireland. The town was mostly rural, with farming being the main industry until the advent of the railroad, which traveled through town towards the Hoosac Tunnel. Today the town industry also includes tourism, with a ski area and other tourist areas along the Mohawk Trail.

In the years preceding the Revolutionary War, as Charlemont's citizens grew increasingly dissatisfied with British rule, Rev. Jonathan Leavitt was installed as the minister of Charlemont's Congregational Church. Born in Walpole, New Hampshire, and graduate of Yale College, Rev. Leavitt arrived in Charlemont in 1767, but his Loyalist sympathies grated on his congregation.

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