The Theater program at Berkshire presents two plays and a musical on the main stage of Allen Theater each year, often performed to a packed house of faculty, students, family and friends, as well as members of the local community. While many students are eager for the opportunity to perform, the program also allows for other theater-related interests to be explored, including technical directing, stage management, set building, sound and lighting.

Recent theater productions include Hairspray, Spamalot, Romeo and Juliet, In The Heights, Grease, Into The Woods and The Crucible. The Theater Department also offers academic classes in Improvisation, which culminate in the BIMP (Berkshire Improv) showcase each semester.