Begun in 1946, with just three plays, the Festival now has approximately 350 entries annually. It began as an idea generated by founder Ken Watts and has flowered into the remarkable annual event we now call the Ontario Drama Festival. For thirty years, until her death in 1981, Ken's wife Ann worked tirelessly with her husband organizing and maintaining the Festival. After his wife's death Wayne Fairhead and Ian Waldron were co-opted by Watts to be his Executive Assistants. Both had served on the Toronto and Districts' Festival Committee for a decade. Watts appointed Fairhead Executive Coordinator of the Festival in 1986, and when he retired in 1991, Fairhead became Executive Director.

The strength of the Festival is rooted in its many dedicated teachers and community members across the Province, who work to ensure that each District Festival is truly a celebration of theatre in their local community. More than 12,000 students and their dedicated teachers are involved annually in the celebrations, garnering some 500 Awards. These include four(4) $3000 Ken & Ann Watts Memorial Foundation Scholarships and four(4)$500 Bursaries awarded to graduating students pursuing a career in the performing arts. As well two (2)$500 Bursaries donated by John Bennie in honour of his late wife Marjory are given for Technical Achievement.

The Festival encourages the writing and development of original scripts and upon his appointment as Executive Director in 1991, Fairhead introduced a Playwriting Award for the 1992 season. The recipient of this Award receives a Bursary of $500. As well, to honour student and teacher writers, he and the late Mira Friedlander edited an anthology of five original scripts entitled CONCRETE DAISY AND OTHER PLAYS for the 45th Anniversary of the Festival. They created Volume 2 for the 50th Anniversary. In 2010 FESTIVAL VOICES: Plays by Students and Teachers for the Sears Ontario Drama Festival was published by Playwrights Canada Press, edited by Fairhead and Jane Gardner of the Carousel Players.

Each year students and teachers from across the Province work diligently to create new and exciting theatre to share with their peers, families, friends and communities through the three levels of the Festival – District, Regional and Ontario Showcase. Learning takes place through professional adjudication, workshops, observation and animated discussions with peers.