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The Chester Playhouse has been a home to the performing arts since it was built in 1938 in Chester, Nova Scotia, by Ken Corkum and Eric Redden. While its first tenant, the Keneric Theatre, operated for over thirty years as a cinema the building wasn't used for live performances until 1963 when the Chester Jesters began five summer seasons of productions.
In the mid-seventies the building was purchased by Leo and Dora Velleman who had done previous puppetry work in Toronto. They renovated the theatre, renamed it the Leading Wind Theatre, and established their theatre group Canadian Puppet Festivals (CPF) at the site. Managed by a board of directors, CPF was a non-profit organization which hosted workshops and puppet productions that included The Pirates of Penzance, and The Mikado. In 1983 the Vellemans retired and CPF merged with Mermaid Theatre.
The Chester Theatre Council (CTC) was founded in 1984 to preserve the Leading Wind Theatre. CTC originally sponsored touring productions but began leasing the building in 1987 as a venue for the first Chester Theatre Festival. In the same year Christopher Ondaatje purchased the theatre and leased it to the council, the theatre's name was changed to the Chester Playhouse, and seating renovations were made. The Ondaatje family donated the playhouse to the CTC in 1992 and the following year the entire building was renovated. In 1999 fundraising for a second wave of improvements began to create a better space for live performances. The renovations were completed in two phases which eventually resulted in new dressing rooms and workshop space, a new green room and new lobby, and an updated electrical system.
The CTC's mission is to "foster, promote, encourage and develop the performing arts and to maintain a community arts facility within the municipality of Chester." To achieve this, the council has managed the Chester Playhouse; hosted both touring companies and other performers; provided a venue for local performing arts groups, including the Chester Drama Society, the Chester Ballet School, and the Chester Brass Band; hosted workshops for all ages; established the Chester Theatre School program and the Chester Theatre Festival; and allowed its space to be used for local meetings. The CTC has brought nationally known performers and musicians to the Playhouse and they have hosted touring productions from Neptune, Rising Tide, and Jest in Time among others.
The Chester Theatre Council is managed by a board of directors consisting of a chairman, vice chairman, secretary, and treasurer. The council is assisted by five committees and the managing director who is responsible for the day to day management and direction of the theatre and is ultimately responsible to the board. Past managing directors include Jane Pyke and Eileen Maxwell (?-1989); Giny Duzak and Jan Morrison (1990); Peter Smith (1991-1996); Chris Heide (ca. 2004); and Erick Bickerdike (ca. 2006). The CTC continues to manage the Playhouse, the Chester Theatre School, and the Chester Theatre Festival.