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Chester Playhouse Summer Series

June 22-September 20, 2025

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. 

The Chester Playhouse's Summer Series does not disappoint. Music, movies, live theatre, and more.

Photo of an audience inside the Chester Playhouse overlooking the stage
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8 Results

A Tribute to Hank Williams featuring Ryan Cook

Part Of: Chester Playhouse Summer Series
A Chester favourite returns, in a concert paying tribute to the country legend behind Hey Good Lookin’, Your Cheatin’ Heart, and Lost Highway, Hank Williams. Friday, July 18th – 7:30 PM Saturday, July 19th – 2:00 PM Saturday, July 19th – 7:30 PM Sunday, July 20th – 2:00 PM Adults – $39.00 ($35.18 +...
Hosted By: Chester Playhouse Theatre
Photo of two people sitting outside the Chester Playhouse on a red bench, entrance in the background

Steph’s Summer Shindig!

Part Of: Chester Playhouse Summer Series
What better way to celebrate summer than with drag superstar Steph Peaks at Steph’s Summertime Shindig ! That’s right, Chester, the incredible Steph Peaks is coming back to Chester Playhouse for another iconic night of laughs and lip syncs! Gather all your 19+ friends and come on out for another...
Hosted By: Chester Playhouse Theatre
Photo of two people sitting outside the Chester Playhouse on a red bench, entrance in the background

Punch Up by Kat Sandler

Part Of: Chester Playhouse Summer Series
Strap in for Punch Up, a comic misadventure that will have you rolling in the aisles as “The Funniest Man Alive” tries to make the “Most Pathetic Man That Ever Existed” make the “Saddest Girl in the World” laugh. Synopsis: Duncan has always been a pretty boring guy, leading a simple life while...

The Sea Shanty Show

Part Of: Chester Playhouse Summer Series
Hoist the mainsail and set course for fun with The Sea Shanty Show, a charming musical review paying tribute to the wonder and majesty of the sea! What started as a TikTok trend has become a worldwide awakening and renewed appreciation for the haunting and harmonious melodies of the sea shanty...

Jenn Grant Trio

Part Of: Chester Playhouse Summer Series
Nova Scotia’s folk/pop princess Jenn Grant makes her Chester Playhouse return, with award-winning songs that will move, excite, and inspire! There is an undeniably ethereal quality to Grant’s voice and her music, described by Australia’s The Age as that of “dreamy, harp-and woodwinds folk, the work...

Terra Spencer & Ian Sherwood

Part Of: Chester Playhouse Summer Series
Two of Nova Scotia’s finest songwriters and storytellers, Terra Spencer & Ian Sherwood, bring their intoxicating blend of musical genius and whimsical storytelling to the Chester Playhouse. Raised on the mud banks of the Avon River, award-winning Nova Scotian funeral director-turned-songwriter Terra...