Charlemont is a highland town with peaks like Pocumtuck Mountain as high as 1872 feet. The town is on the Mohawk Trail, the primary Indian route between the Hudson River Valley and the Connecticut River Valley, and was the site of forts built in 1744 as part of the line of defense to protect settlers further south from Indian attack during the French and Indian wars. In fact, sections of the town were abandoned by their residents in 1746 after the attack and destruction of Fort Massachusetts by French and Indian forces.

Exposure to this kind of attack slowed the community's development. When the ending of the wars stabilized the area, the town grew as an agricultural and industrial site with grist and saw mills, brick yards, potash production, furs, hides and palm leaf hats. 

Charlemont was agricultural through the mid-20th century. Bisected by the Deerfield River, the town is now a rural recreation center and because of its location on the Mohawk Trail, was the site of a very early flow of tourists. The town hosts a number of recreational and second homes and there is some ski resort development.