The Shadowbox Theatre

06/07/2026

Attention lovers of improvisation!

Beginning Sunday, 14 June 2026, The Theatre Skills Education Program is offering three(3) unique courses focused on the art of improvisation, taught by two of the most experienced and highly regarded improv artists in our region.

Whether you’re a youth between the ages of 10-16 looking to learn the foundational elements and necessary skills of improv, a novice looking to break into the world of improv performance (or refine the skills you’ve already learned), or an experienced performer looking for the next steps in their improv journey – there’s a course for everyone seeking to learn!

All three courses begin Sunday, 14 June 2026 and continue every Sunday afternoon for four(4) weeks. Details can be found at the link below. REGISTRATION DEADLINE is 11:59 pm, Friday 12 June 2026. Spots are limited so register TODAY!

All courses and workshops are held at The Shadowbox Theatre (1501 Howard Ave. - corner of Howard & Shepherd - Windsor ONT). TO REGISTER click on links provided in course descriptions. Open to...

05/30/2026

“RYT feels that anything that teaches a new skill or allows the kids to improve upon existing skills is always a win.”

Thanks to Marc Rocheleau from windsoriteDOTca - windsor's hyper-local news & culture for this wonderful article about the 2nd Edele Winnie YOUTH Monologue Competition!

Facebook won't let us share the article, so check it out at the link below -- then join us tonight (30 May 2026) at The Shadowbox Theatre to cheer on the kids and help determine the winners!

WHEN: 30 May 2026 @ 7:00 pm (doors open 6:30)

WHERE: The Shadowbox Theatre (1501 Howard ave. - corner of Howard & Shepherd - Windsor, ON)

​HOW MUCH: $15 at the door (cash, debit, or credit card)

“RYT feels that anything that teaches a new skill or allows the kids to improve upon existing skills is always a win.” Thanks to Marc Rocheleau from WindsoriteDOTca for this wonderful article...

05/30/2026

Tonight is the final performance of the 2nd Edele Winnie YOUTH Monologue Competition! The show starts at 8:00 pm -- and you can get your tickets at the door for only $15. Check out this article by Marc Rocheleau of windsoriteDOTca - windsor's hyper-local news & culture then come on down to The Shadowbox Theatre to cheer the kids on and help determine the winners!

Continuing its popularity amongst youth, a familiar competition is back to showcase local talent. Taking place at the Shadowbox Theatre (located at 103b – 1501 Howard Avenue) on Friday May 29 and S...

05/25/2026

This Friday & Saturday night (May 29th & 30th, 2026) at 8:00 pm, the Edele Winnie YOUTH Monologue Competition returns to The Shadowbox Theatre!

This year fourteen(14) contestants will perform original monologues written by Edele Winnie in front of a panel of judges and an enthusiastic audience -- AND YOU CAN HELP DECIDE THE WINNERS! Cash prizes will be awarded to the top three performers in each age category following the second night of performances on May 30th.

WHEN: May 29 & 30, 2026 @ 8:00 PM (doors open 7:30)

WHERE: The Shadowbox Theatre (1501 Howard ave. – corner of Howard & Shepherd – Windsor, ON)

HOW MUCH: $15 at the door (cash, debit, or credit card)

The 2nd Edele Winnie YOUTH Monologue Competition is produced by Revolution Youth Theatre in association with Edele Winnie.

The age categories: Seniors - ages 16 to 18; Juniors - ages 12 to 15; and Minis - ages 8 to 11

05/18/2026

Treat yourself to an unforgettable evening of wonder and close-up magic at MagicBox: An Evening of Wonder, only at The Shadowbox Theatre -- featuring FOUR world-class magicians! This Saturday, 23 May 2026 at 8:00pm (doors open 7:30pm). Tickets are on sale now for $25 via postproductionswindsor.ca or take your chances at the door (cash, debit, or credit card) if seats are still available.

Click the link to learn more and get your tickets today!



https://bizxmagazine.com/events/magicbox-an-evening-of-wonder/

MagicBox: An Evening of Wonder. Renown magicians Chris Philpott, Eric Bedard, Dreygon, and Johnny New York return to the Shadowbox stage

05/15/2026

After a successful run at the Masonic Temple Ballroom earlier this year, writer and director Barry T. Brodie and Post Productions will remount his latest theatrical vision, An Echo of the Soul: Tchaikovsky and His Women, at The Shadowbox Theatre this June.

An Echo of the Soul tells the story of Russian composer Piotr Ilyich Tchaikovsky and the two women who changed the course of his life. Starring Heath Camlis, Cindy Pastorius, and Shayla Hudson. Learn more and buy your tickets today at https://www.postproductionswindsor.ca/

WHEN: June 19, 20, 25, 26 & 27, 2026 @ 7:30 PM (doors open 7:00). MATINEE Saturday 20 June 2026 @ 2:00 PM (doors open 1:30)

WHERE: The Shadowbox Theatre (1501 Howard ave. - corner of Howard & Shepherd - Windsor, ON)

HOW MUCH: $25 via https://www.postproductionswindsor.ca/

05/14/2026

IRL Presents: The Newcomers Stand-up Comedy Show at The Shadowbox Theatre!

Prepare yourselves for uproarious laughter as host and comedy legend Dave "Squeaky Wheelz" welcomes local newcomers to the stand-up comedy scene! You'll see some familiar improv performers get on stage and try something a little different -- and, as an extra special treat, the show will feature Toronto Headliner Cole Chauvin!

WHEN: Friday, 5 June 2026 @ 7:00 PM (doors open 6:30)

WHERE: The Shadowbox Theatre (1501 Howard ave. - corner of Howard & Shepherd -- Windsor, ON)

HOW MUCH: $20 via https://www.postproductionswindsor.ca/ or take your chances at the door (cash, debit, or credit card) if seats are still available.

FEATURED NEWCOMERS:
Kevin Doak, Nolan Mayrand, Akeel Blake, Cristian Picard, Ian Reuten, and Anthony Giacalone

IRL is teaming up with Windsor comedy legend Dave Squeaky Wheelz to welcome local newcomers to the stand-up comedy scene & that's not all!

05/13/2026

Kick off your summer with wonder on Saturday, 23 May 2026 at 8:00 PM with MagicBox: An Evening of Wonder!

Treat yourself to an unforgettable evening of astounding and awe inspiring close-up magic at The Shadowbox Theatre, featuring four world-class magicians!

Renown magicians Chris Philpott, Eric Bedard, Dreygon, and Johnny New York return to the Shadowbox stage for an outstanding display of close-up magic that will leave you wide-eyed and thirsty for more! Learn more about each of these fine and talented artists via https://www.postproductionswindsor.ca/magicbox.html

WHEN: Saturday, 23 May 2026 @ 8:00 pm (doors open 7:30)

WHERE: The Shadowbox Theatre (1501 Howard ave. -- corner of Howard & Shepherd -- Windsor, ON)

HOW MUCH: $25 via postproductionswindsor.ca or take your chances at the door (cash, debit, or credit card) if seats are still available.

Treat yourself to an unforgettable evening of wonder and close-up magic at The Shadowbox Theatre, featuring FOUR world-class magicians!

05/05/2026

Card Board Game Night returns on Monday, 18 May 2026 with EXTENDED HOURS for Victoria Day!

Join us at The Shadowbox Theatre, where you can play some games with old friends and new for just $5. The best part? You only have to pay ONCE for the day -- re-entry is FREE!

Doors open at 1:00 pm. Drop in any time before 9:00 pm to get in at least one game AND enter your name in the door prize draw for a chance to win a brand-new board or card game of your very own!

For more information click on the event link or visit https://www.postproductionswindsor.ca/card-board-game-night.html

WHEN: Monday, 18 May 2026. 1:00 pm - 10:00 pm. Drop in any time before 9:00 pm to play at least one game.

WHERE: The Shadowbox Theatre (1501 Howard ave. -- corner of Howard & Shepherd -- Windsor, ON)

HOW MUCH: $5 per person at the door (cash, debit, and credit accepted)

If you have any questions, would like to make requests for future game nights, or even get a complete list of available games, contact Ian Reuten at [email protected].

05/05/2026

Did you know IRL Season 3 League Nights are open to the public? Well, they are! For only $5 YOU can enjoy all the hijinks and shenanigans IRL - Improv Recreation League has to offer this season as the teams compete for laughs and votes and special recognition leading up to the Finals Night on May 30th.

WHEN: May 5, 12, 19 & 26 @ 6:30 PM (doors open 6:00)

WHERE: The Shadowbox Theatre (1501 Howard ave - corner of Howard & Shepherd - Windsor, Ontario)

HOW MUCH: only $5 at the door (cash, debit, or credit card)

Presented by IRL - Improv Recreation League and Post Productions.