The first skiing trails on Wachusett Mountain were cut by the Civilian Conservation Corps in the late 1930’s, with the first lift being introduced in 1960.

Wachusett Mountain has a long history of tourism on the mountain. The first hotel was constructed on the summit in 1882. A new summit hotel was constructed in 1907 and continued operations until it was destroyed by fire in 1970. Over 600,000 people visit the mountain year round with at least half of that number visiting the Wachusett Mountain State Reservation in the summer and fall.

Ralph Crowley was awarded lease from the state to operate Wachusett Mountain in 1969. Located within the Wachusett Mountain State Reservation, Wachusett Mountain Ski Area operates in cooperation with the Massachusetts Department of Conservation and Recreation, providing skiing and snowboarding on 100 acres of terrain within a 450-acre leased area. A major expansion was completed in 1982 which included the construction of the current base lodge.