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Chester Playhouse - Summer 2026

June-August 2026

Located in the village of Chester, Nova Scotia, join us for world-class performances including theatre, music, comedy, movies, community events, and more!

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Overview of events at the Chester Playhouse

 

Calendar Events

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12 Results

The Baby Tyler Show (Theatre/Puppetry)

This event is not organized by the Municipality of Chester.
Our information may have errors and/or be out of date.
Please confirm details with the host.
Calling it a puppet show doesn’t quite capture the magic of The Baby Tyler Show. What we can call it is – surprising, hilarious, and unlike anything you’ve seen before! Join us for this uniquely joyful performance, where laughter and high stakes drama are conjured from the smallest of objects, live...

In Conversation: Gillian Deacon

This event is not organized by the Municipality of Chester.
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Please confirm details with the host.
Join host Liz Crocker in conversation with veteran journalist, television and radio host, and bestselling author, Gillian Deacon. Award-winning broadcaster and bestselling author Gillian Deacon spent over 10 years as host of Here & Now, Toronto’s afternoon drive show on CBC Radio One. She is a...

Ron Sexsmith

This event is not organized by the Municipality of Chester.
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Please confirm details with the host.
Summer 2026 at the Chester Playhouse kicks off with one of Canada’s most accomplished singer-songwriters, Ron Sexsmith. Ron Sexsmith is a three-time Juno award-winning songwriter from Ontario, Canada. He has written and recorded an extensive and acclaimed catalog of studio albums and original songs...

Gypsy - The Premiere Fleetwood Mac Tribute

This event is not organized by the Municipality of Chester.
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Please confirm details with the host.
A smash hit at their sold out concert in 2023, Nova Scotia’s #1 Fleetwood Mac Tribute – Gypsy, takes the stage with all your favourite songs “Gypsy” The Premiere “Fleetwood Mac” Tribute features accomplished musicians, who deliver a world-class show! The songs of this iconic band transcend across...

The Family Crow: A Murder Mystery

This event is not organized by the Municipality of Chester.
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Please confirm details with the host.
Puppets! Puns! Murder! The Family Crow: A Murder Mystery is a laugh-out-loud puppet comedy crafted by internationally acclaimed Off-Broadway puppeteer Adam Francis Proulx. Synopsis: When a shocking murder rocks the Family Crow, it’s up to Horatio P. Corvus – Sorter Outer of Murders – to uncover the...

Emilio's A Million Chameleons

This event is not organized by the Municipality of Chester.
Our information may have errors and/or be out of date.
Please confirm details with the host.
Emilio’s A Million Chameleons is a dazzling, heartwarming musical about embracing who you truly are, supporting one another, and letting your inner sparkle shine. Appropriate for ages 4 to 104, the whole family will delight in this puppet-filled romp! Synopsis: Emilio Jr. is determined to carry on...

Hot Flash Comedy with Syd Bosel

This event is not organized by the Municipality of Chester.
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Canadian Comedian Syd Bosel brings her Hot Flash Comedy tour to Chester this July! After years lighting up stages in Vancouver and across BC, Syd Bosel is an award-winning, touring comic. Her signature style blends raw honesty with hilarious insight, making her a crowd-favourite. With unfiltered...

Aquakultre : 1783 Live

This event is not organized by the Municipality of Chester.
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Join us for a very special Pay-What-You-Can concert as Lance Sampson, aka Aquakultre celebrates the release of his groundbreaking album, 1783, which seamlessly blends a range of historically Black music, with hints of gospel, blues, jazz, and soul, mixed in with vintage R&B overtones. An uncommonly...

Ventastic: Reimagining the Art of Ventriloquism

This event is not organized by the Municipality of Chester.
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Award-winning ventriloquist Michael Harrison takes the “long-lost art” of ventriloquism and turns it upside down with his hit show, Ventastic . With 30+ years of experience—including a standout run on America’s Got Talent—Michael Harrison tours the globe with his hit show, Ventastic. Whether he’s...

Fiddles & Feet

This event is not organized by the Municipality of Chester.
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Please confirm details with the host.
After an incredible run of sold out shows in 2024, we are thrilled to welcome Fiddles & Feet back to the Chester Playhouse this August! Fiddles & Feet is a high-energy, seven-piece ensemble bringing the heart and soul of the East Coast to stages across Nova Scotia and beyond. Following a standout...