Charlemont was first colonized by Moses Rice (1694–1755) who purchased 2,200 acres (8.9 km2) on April 23, 1743, that been previously set off as Boston Township Number 1 in 1735 by the Great and General Court.

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.

In the years preceding the Revolutionary War, as Charlemont's citizens grew increasingly dissatisfied with British rule, Rev.

[5] 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.

[6] 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,[7] sheltering many escaped slaves on their journeys northward.

[8] Revolutionary War soldier and historian Lemuel Roberts helped his father establish a farm in Charlemont before leaving to fight in the Siege of Boston.

The town is bordered by Rowe to the northwest, Heath to the northeast, Colrain and Shelburne to the east, Buckland to the southeast, Hawley to the southwest, and Savoy and Florida to the west.

Near the center of town, the road also junctions with, and shares a short, 0.6-mile (0.97 km) concurrency with Route 8A.

Along the southern bank of the river, a stretch of the Guilford Rail System leads freight trains from Greenfield towards the Hoosac Tunnel in neighboring Florida, towards New York.

The town lies at the westernmost point of the Charlemont-Greenfield line (Route 41) of the Franklin Regional Transit Authority (FRTA), with a scheduled stop at the Federated Church.

Charlemont employs the open town meeting form of government, and is led by a Select board.

[23] The town is patrolled by the Second (Shelburne Falls) Station of Troop "B" of the Massachusetts State Police.

Charlemont is a member of the Mohawk Trail Regional School District, along with Ashfield, Buckland, Colrain, Hawley, Heath, Plainfield, Rowe, and Shelburne.