Performances on Hebron's stage integrate life, literacy, learning, and community, and celebrate the strong character development that is a hallmark of Hebron's educational experience. Young actors and actresses learn public speaking skills they will draw on throughout their lives; they explore different roles and personalities, and often find within themselves something that can only be discovered through a dramatic performance. Students working backstage develop knowledge of construction, design, and artistic techniques, or learn stage management and production skills.

Student dramatic performances are one of the highlights of the year, both in the Middle and Upper Schools. Three out of four Hebron students have played a role in at least one Hebron production. The all-school musical takes place near the end of winter term. The production is supported by faculty directors, student and professional musicians, and a group of committed Upper School thespians. It is open to the entire school community, including students and faculty who are also involved in an after school sport.

Recent shows, which have boasted casts of over fifty students, include Working, Grease, Joseph & the Amazing Technicolor Dreamcoat, and The Wiz. Middle Schoolers take the stage in March. In the spring, during the Arts Festival, Upper School students cast, direct, and produce one-act plays.

For the past two years, Hebron Academy has also been fortunate to welcome The Theater at Monmouth to campus. The Theater of Monmouth is one of just 22 professional theaters across the nation to take part in the National Endowment for the Arts' Shakespeare in American Communities program. They have performed Henry V and the Merry Wives of Windsor, and the directors and actors have brought master classes to Hebron students.