Pioneer Theatre is Heritage High School's award winning drama program. Heritage High School's Pioneer Theatre is a student run program with Theatre Director Larry Hart and Technical Director, Taylor Wisskirchen. In 2010, the Virginia Theatre Association named Director Larry Hart Theatre Educator of the Year.

In the fall of 2023 the Acting II class placed 2nd at the Virginia Theatre Association's annual conference. This allows Pioneer Theatre to attend and compete at the national level at Southeastern Theatre Conference in Mobile, Alabama. HHS is blessed with an amazing amount of talented students.