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The theater program at Canterbury is open to all students, whether a novice or a veteran to the stage or to stagecraft.

Students work primarily in two spaces: the recently renovated Maguire Auditorium, one of the central gathering spaces for school meetings, concerts, guest speakers, and theater presentations, and the L. Michael Sheehy '56 Choral Classroom, a flexible classroom, rehearsal, and performance space for several performing ensembles and individual recitals. All students are encouraged to participate, either as actors, or as members of the technical crew, building the sets, costumes, and props for the fall and spring productions.

Each fall students typically perform in a non-musical play on the Maguire stage. Rehearsals for the fall production are held in the evenings prior to study hall in order to maximize the number of students who can participate. In the winter, students are involved in a smaller production held in the L. Michael Sheehy '56 Choral Classroom. This production is rehearsed during the afternoons and is considered a winter sports alternative. In the spring, a major musical is presented, with a professional pit band or orchestra. Just as in the fall, the cast and crew work on this production in Maguire in the evenings.

Faculty also love getting involved in the program. In addition to two directors that are full-time faculty members, Canterbury has a part-time technical director and many faculty members who volunteer their time and talents on and off the stage. Creative students are nurtured here at Canterbury, and many have performed in or worked on every production during their years as students here. Many have gone on to be involved in theater as professionals, or as members of community theaters; all involved students develop a love and respect for theater that lasts long after they leave the hilltop.