Charlemont was first settled by Moses Rice (1694-1755) who purchased 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.
By 1777 the situation came to a stand-off: Leavitt refused to accept his salary in rapidly depreciating colonial currency. So the town voted to simply close the church, and it stationed a constable at the door to bar the offending reverend. But Leavitt would not be deterred: He moved his sermons to the schoolhouse, where he held forth until 1785, when he was finally dismissed. He sued for his salary, as well as his loss on the depreciated colonial currency, and was awarded £700.
Leavitt's descendants continued to remain in Charlemont and the surrounding region, and several—including Col. Roger Hooker Leavitt, who represented Charlemont in the Massachusetts House of Representatives, and his brother Hart Leavitt—became notable operators of stations on the Underground Railroad, sheltering many escaped slaves on their journeys northward.