This weekend in Collingwood is packed with exciting events, perfect for a variety of interests. Join us from Friday, February 13th, through Sunday, February 15th, for comedy shows, musical performances, and heartwarming plays. Whether you’re looking for a night of laughter or a romantic outing, there’s something for everyone to enjoy!
Events In Collingwood This Weekend Friday Feb 13th – Sunday Feb 15th
First Date: A Musical Comedy – Friday, Feb 13th
- Date: February 13th, 2026
- Time: 8:00 PM – 10:30 PM
- Venue: The Historic Gayety Theatre
- Address: 161 Hurontario St, Collingwood, ON L9Y 2M1
FIRST DATE is a laugh-out-loud musical comedy about modern dating and one very awkward night out. When a nervous first-timer meets a confident serial dater, a simple drink quickly turns into a spiral of overthinking, bad instincts, and inner voices saying exactly the wrong thing. If you have ever survived dating apps, mixed signals, or a first date you could not escape fast enough, this show is for you.
Collingwood Blues vs. Georgetown Raiders – Friday, Feb 13th
- Date: February 13th, 2026
- Time: 7:00 PM – 9:00 PM
- Venue: Eddie Bush Memorial Arena
- Address: 97 Hurontario St, Collingwood, ON L9Y 4V2
Go Blues Go! Watch your Mike Jackson Collingwood Blues take on the Georgetown Raiders in an exciting hockey match. Come out and support the team while enjoying the thrill of live sports.
Love Letters – Dean Hollin & Tara Kivlichan – Friday, Feb 13th
- Date: February 13th, 2026
- Time: 7:30 PM – 9:00 PM
- Venue: Simcoe Street Theatre
- Address: 65 Simcoe St Studio 7, Collingwood, ON L9Y 1H7
A.R. Gurney’s Love Letters is a tender and quietly powerful play told through decades of correspondence between two lifelong friends. This performance features Dean Hollin and Tara Kivlichan, bringing warmth, humour, and emotional depth to this timeless story of connection and love.
Grey Road 1 – Friday, Feb 13th
- Date: February 13th, 2026
- Time: 8:00 PM – 11:00 PM
- Venue: Harbour Street Fish Bar
- Address: 10 Keith Avenue, Unit 403, Collingwood, ON, Canada
Grey Road 1 delivers a powerful mix of classic rock, funk, and blues. Named after frontman Fred Dawson’s childhood home, the band has been igniting Ontario stages for over a decade with raw energy and groove. Don’t miss this electrifying performance!
The Ava Val-entines Comedy Special – Saturday, Feb 14th
- Date: February 14th, 2026
- Time: 7:00 PM – 9:30 PM
- Venue: Taps and Tunes Bar and Grill
- Address: 18 Huron Street, Collingwood, ON L9Y 1C4
Get ready to laugh your heart out with Ava Val’s hilarious Valentine’s comedy bash, featuring opening act Dan Galea, at Taps and Tunes Bar and Grill. This event promises a night filled with laughter and fun—perfect for celebrating love and friendship!
Saturday Morning Sound Bath in Downtown Collingwood with Jay Robinson – Saturday, Feb 14th
- Date: February 14th, 2026
- Time: 10:00 AM – 11:00 AM
- Venue: Lotus Sound
- Address: 87B Hurontario Street, Collingwood, ON L9Y 2L9
Join Jay Robinson for a 60-minute immersive sound bath featuring gongs, handpan, singing bowls, and more at Lotus Sound. This relaxing experience is perfect for those looking to unwind and rejuvenate on Valentine’s Day.
First Date: A Musical Comedy – Saturday, Feb 14th
- Date: February 14th, 2026
- Time: 3:00 PM – 5:30 PM
- Venue: The Historic Gayety Theatre
- Address: 161 Hurontario St, Collingwood, ON L9Y 2M1
Join us for the second showing of FIRST DATE—a laugh-out-loud musical comedy about modern dating. This lively performance will take you through the ups and downs of a first date with all its awkward moments. It’s the perfect prelude to a romantic evening!
Love Letters – Chelsea Coulter & John Knox – Saturday, Feb 14th
- Date: February 14th, 2026
- Time: 2:00 PM – 3:30 PM
- Venue: Simcoe Street Theatre
- Address: 65 Simcoe St Studio 7, Collingwood, ON L9Y 1H7
A.R. Gurney’s Love Letters explores love, distance, and memory through a lifetime of written correspondence. This matinee performance stars Chelsea Coulter and John Knox, offering an intimate and heartfelt interpretation of this beloved play.
Love Letters – Jake McArthur & Shirley Joost – Saturday, Feb 14th
- Date: February 14th, 2026
- Time: 7:30 PM – 9:00 PM
- Venue: Simcoe Street Theatre
- Address: 65 Simcoe St Studio 7, Collingwood, ON L9Y 1H7
Experience another performance of A.R. Gurney’s Love Letters, this time featuring Jake McArthur and Shirley Joost. The simplicity of the play beautifully reveals how love can endure through words shared over a lifetime. A must-see for theatre lovers!
First Date: A Musical Comedy – Sunday, Feb 15th
- Date: February 15th, 2026
- Time: 3:00 PM – 5:30 PM
- Venue: The Historic Gayety Theatre
- Address: 161 Hurontario St, Collingwood, ON L9Y 2M1
Catch the final showing of FIRST DATE on Sunday afternoon. This hilarious musical comedy explores the awkwardness of modern dating and is the perfect way to wrap up your weekend. Don’t miss this chance to laugh and relate to the characters’ experiences!