AST has a long and unique history in the arts, and its roots in the international community of Tangier have linked the school to a long list of artists and luminaries. The hallways of AST are graced with original work by Claudio Bravo, Brian Gysin, and Christo among others, and artists such as Paul Bowles and Yves Saint-Laurent have collaborated with the productions of the Dramatic Society of AST, the most prominent artistic tradition of the school. Although subjects such as dance and fine art painting have perennially been a part of the AST curriculum, the arts are currently represented in the areas of Music and Drama. In the Lower School, these disciplines are combined in the annual Christmas Pageant which currently takes the form of an original piece of musical theater each season. Apart from the Christmas show, the Lower School arts program focuses on expression and creativity, whether the instrument be a drum or the human body through process-based exercises that incorporate music, drama, and dance. The annual presentation of the AST Dramatic Society is one of the cornerstones of the arts at the school.

Founded in 1967 by the late Headmaster Joseph A. McPhillips III, the Dramatic Society has produced a play every year since, often selecting challenging classical texts or modern dramas not commonly produced by high schools. Each June, the yearly performance takes center stage and students, faculty, and community members come together to present challenging work of high quality, marked by a powerful, minimalist aesthetic.

AST relies on non-traditional venues to house annual events. One performance of Tennessee Williams's Ten Blocks on the Camino Real, under the direction of Joseph A. McPhillips III, cordoned off a center square of Tangier's ancient medina to stage the play in the very location where Williams wrote it. Following the passing of Mr. McPhillips III in 2007, the school has endeavored to maintain a high standard in its theatre program, and as the school moves forward, this legacy will continue to be honored as a vital and unique part of the AST experience.