Wayside Theatre was founded in the early 1960s by Leo M. Bernstein following his purchase of a former movie theatre located on Main Street in Middletown, Virginia. The company staged their first performance in 1963. In 1968, Gerald (Gerry) Slavet took over as Artistic Director, bringing with him an interest in working with local teachers to bring theatre into the classroom, which led to the formation of Wayside Theatre on Tour (WTOT). One of the most successful outreach programs in Wayside Theatre's history, WTOT brought professional theatrical performances, completely separate from the mainstage productions, into the local community, particularly to elementary schools. To emphasize the educational aspect of the program, teachers were provided with study guides to be used in their classrooms to prepare students for the performances and post-performance question and answer sessions. These study guides were initially developed and produced largely by the newly hired Director of Public Relations and Publicity Barbara Swink. All WTOT productions were cast with professional actors, many who had appeared on Broadway or with other professional theatre groups throughout the country, including actress Kathy Bates (credited as Bobo Bates) who performed with WTOT during the 1973 season.

Slavet formally announced his intention to step down from his role as Artistic Director in early 1974, but agreed to stay on and assist with planning the upcoming season before handing over the role to his successor Lou Furman in 1975. Both WTOT and Wayside Theatre continued to operate for the next 40 years, with WTOT shifting focus from touring venues in the community to inviting school groups to attend performances at the physical theatre itself sometime in the early 2000s. In total, Wayside Theatre operated for 50 years, becoming the oldest professional theatre in Virigina, before financial troubles led to its sudden closing in 2013.