The Pioneer Playhouse was built by Col. Eben C. Henson, who established the outdoor theater in 1950. Notable alumni actors include John Travolta, Lee Majors, then known as Harvey Yeary, and Jim Varney.

Since Henson's death in 2004, the theater had been run by Henson's widow, Charlotte, as producer, and her daughter, Holly, who served as artistic director until her death in 2012.

Robby Henson, Charlotte's son, directs at least one play at the theater every summer.

After Holly's death, her siblings, Robby and Heather, returned to the Playhouse full-time to help their mother run the business.

Charlotte, who always selected the plays for each season, died in February 2024, just a few months prior to the start of the Playhouse's 75th Anniversary season.