Bringing community together since 1938!

Since 1938 friends, families and visitors to our community have been gathering at 22 Pleasant Street in Chester to experience movies, music, theatre and community events. A supportive and generous community has kept this jewel alive and thriving as an important arts venue on the south shore of Nova Scotia.


Land Acknowledgment

We are in Mi’kma’ki, the ancestral and unceded land of the Mi’kmaq People. The area where the Chester Playhouse is situated is known as Meneskwe’k, which roughly translates to “the marshy place”. We honour the Treaties of Peace and Friendship, and we would like to pay our respects to the Elders, past and present, as we continue to work in our community toward reconciliation on a daily basis. We are all treaty people.  This practice, of acknowledging the original inhabitants of this land, is itself an Indigenous practice.  We offer it to affirm our commitment to learning and working towards a more equitable world, and to invite you to join us on this journey.


The History of 22 Pleasant Street

The building that is now known as the Chester Playhouse was built in 1938 and operated as the Kenerik movie house for many years. Starting in 1963, it was used as a venue for annual summer theatre productions by the Chester Jesters, but then sat unused until 1975 when it was purchased by Leo and Dora Velleman and Canadian Puppet Festivals. They used the building until merging with Mermaid Theatre in 1983.

Then after a brief dormant period, the Chester Theatre Council brought the Playhouse to life again with the first Chester Summer Festival in 1987, a series of touring shows over an eight-week period. That fall the building was purchased by Sir Christopher Ondaatje and renamed the Chester Playhouse. In 1992, he donated the Playhouse to the Chester Theatre Council, a registered charity with a volunteer Board of Directors that continues to operate the Playhouse today.

The Chester Playhouse now showcases established and emerging musicians, professional theatre, Hollywood, and independent films, and welcomes community talent to the stage.

Chester Playhouse old facade



1938 – Kenerik Movie House

The Playhouse was originally built by Ken Corkum and Erik Redden as a movie theatre named Kenerik.


1963 – Chester Jesters

The beginning of a true theatre and entertainment centre in the village of Chester, both for the people and of the people. Dick and Teka Burwell directed the Chester Jesters in the first of five annual summer productions. Dick, known fondly as “The Broom”, created, wrote, directed and produced a play every summer. Teka was the “behind the curtains worker” as she knew the community and could recruit people to support such a venture. Chester Jesters was designed as a project in which the entire village could play a part, and they did!

After the Chester Jesters retired, the building lay dormant for several years…


1975 – Leading Wind Theatre

Leo and Dora Velleman purchased the building in 1975, renovated it and renamed it the “Leading Wind Theatre” after a clipper ship that counted Chester among its ports of call.

The Velleman’s company, Canadian Puppet Festivals, operated from the theatre until merging with Mermaid Theatre in 1983.


1984 – The Chester Theatre Council

The Chester Theatre Council (CTC) was founded in 1984 to preserve the Leading Wind Theatre as a performing arts centre for the municipality of Chester.

The mission of the Chester Theatre Council in 1984 was to “foster, promote, encourage and develop the performing arts and to maintain a community arts facility within the Municipality of Chester”.


1987 – Renamed Chester Playhouse

The building lay idle until 1987 when the Chester Theatre Council presented its first Chester Summer Festival production in July of that year, “Side By Side By Sondheim”. Thus began the tradition of presenting quality musicals and drama to our residents and summer visitors. In the fall of 1987, the building was purchased by Sir Christopher Ondaatje, renamed the Chester Playhouse.


1988 – More Permanent Seats

To increase the seating in the Playhouse permanent seats were added to the balcony bringing the capacity of the house to 176 seats.


1992 – Donated to the Council

The Ondaatje family donated the Playhouse to the Chester Theatre Council in 1992 and the following year the entire building was renovated.


1999 – Raising the Roof

Additional renovations were done to make the Chester Playhouse a modern and comfortable facility for performers and patrons. Work done included a two-story addition to the back of the building which incorporates dressing rooms and a Green Room for performers, a workshop in which to create props and sets, and an updated electrical system. Additional donations allowed work to begin at the front of the building including a new upper lobby and re-established office space under a new (raised) roof.


2005 – Completion

The renovation project was completed in 2005 with the replacement of the original Box Office, an upgraded entry lobby, new washrooms, carpeting and a small art gallery.


2019 – Ruby Jubilee

The Chester Playhouse celebrated its Ruby Jubilee with its 80th anniversary of entertainment featuring Music, Theatre and Film in the Playhouse. Through the continued support of ticket patrons, donors, sponsors, advertisers, volunteers, and government funders, we promised to build upon the rich history of the Playhouse and attract the finest musicians and actors from our region and beyond, entertain our patrons and provide learning and performing opportunities for youth.


2020/2021 – Restoration Project

By 2020, the Playhouse needed critical structural work to meet the expectations and needs of audience members, performing artists and the community.

We are pleased to share that the three levels of government – the Municipality of Chester, The Province of Nova Scotia, and the Government of Canada – agree The Chester Playhouse is vital to the cultural, social, and economic health of the community and collectively invested $803,000 in the restoration of the Playhouse!

Equally important, the Restoration Project included donations from over 150 private donors from across our community, who contributed over $450,000 to this project.  The restored Playhouse will be more accessible, will be comfortable year-round and will be equipped with the technical equipment required to proudly showcase music, theatre, film and community programs.


2021 Fire

On June 10, 2021, weeks away from the completion of the Restoration Project, fire struck this beloved building, causing extensive damage to the roof and performance space.  Thankfully, no one was hurt, and we remain grateful to the 18 fire departments from across the province that came together and worked so bravely to extinguish the fire with minimal damage to neighbouring buildings.

Suddenly without a venue, our team quickly reimagined our summer programming, to present incredible live performances outside and in venues around the Village of Chester.  We are committed to seizing the opportunity afforded by our “Playhouse Without Walls” to bring incredible live performances to people across our municipality, as we work to rebuild our beloved venue.


2022 Rebuild Project

The Rebuild Project officially started in Spring of 2022 and we really started to see progress as the summer began. Your new Playhouse will be better than ever, with our team working hard to seize opportunities to make the building greener, more accessible, and better equipped than ever to meet the needs of today’s artists and audiences. You can follow the progress of the Rebuild Project on our NEWS page!



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