What's Happening: Windsor

Windsor International Film Festival Screenings

Date: Wednesday, May 27 – Thursday, May 28
Time: See Schedule
Location: Capitol Theatre Windsor
Summary: Discover some great dramas and comedies at WIFF this month!

Windsor Police Women'Session Information Session & Prep Practice

Date: Thursday, May 28
Time: 5:00 pm – 7:00 pm
Location: St. Clair College Windsor Campus
Tickets: Free
Summary: Gain an insight into the recruitment process for a career at Windsor Police Service.

Innovation Blueprint: Windsor

Date: Thursday, May 28
Time: 5:30 pm – 7:00 pm
Location: Windsor Hall
Tickets: Free
Summary: Join us for an informative hour of entrepreneurial insights and inspiration!

Country Line Dance At Walkerville Brewery

Date: Thursday, May 28 – Friday, May 29
Time: 6:00 pm – 9:00 pm
Location: Walkerville Brewery
Tickets: $10.00
Summary: Join us for a high-energy Country Line Dancing Night filled with great music, easy-to-follow steps, and one heck of a good time!

Cat Clyde with Joe Abbott at Meteor

Date: Thursday, May 28
Time: 8:00 pm
Location: Meteor
Summary: Catch Cat Clyde live at Meteor on May 28 with special guest Joe Abbott for a soulful night of folk, blues, and country-infused storytelling.

Essex Glow Ride

Date: Friday, May 29
Time: 6:00 pm
Location: Town of Essex
Summary: Join us for Bike Windsor Essex’s bike rodeo, fire truck tours, bike decorating, crafts, prize draws, a free BBQ presented by Rotary Club of Essex and more!

Comedy Night for Parents with Mom Said Duck

Date: Friday, May 29
Time: 7:00 pm
Location: Capitol Theatre Windsor
Summary: Moms—this is your night out.

Lake St. Clair King of The Lake Walleye Tournament

Date: Saturday, May 30
Time: 6:00 am
Location: Stoney Point Sportsmen’s Club
Summary: Come on out to what should be a great day of fishing on Lake St. Clair! Contact for details and start times.

Downtown Windsor Farmers’ Market

Date: Saturday, May 30
Time: 9:00 am
Location: Pelissier Street (between Wyandotte & Park)
Summary: Discover fresh local produce, artisan foods, family fun, and community events at the Downtown Windsor Farmers’ Market.

Mr. Surprise Windsor Grand Opening (Pre-Registration)

Date: Saturday, May 30 – Sunday, May 31
Time: 10:00 am – 5:00 pm
Location: Devonshire Mall
Tickets: Free
Summary: Join us for the Mr. Surprise Windsor Grand Opening! Plan your visit and receive a special freebie gift (limit 1 per person).

Pelee Island Winery Half Marathon

Date: Saturday, May 30
Time: 10:00 am
Location: Pelee Island Winery
Summary: Welcome to the 12th running of the Pelee Island Winery Half Marathon. See website for details.

A Decade of Distilling | Complimentary Guided Tours at Wolfhead

Date: Saturday, May 30
Time: 11:00 am
Location: Wolfhead Distillery
Summary: Join us this May as we celebrate 10 years of distilling in Amherstburg with a special thank you to our guests.

Black Boys Code Windsor - Robo-Race Challenge: Optimize & Compete

Date: Saturday, May 30
Time: 11:00 am – 3:00 pm
Location: University of Windsor
Tickets: Free
Summary: Join us for an exciting Robotics workshop designed just for boys aged 8-17! Whether they’re brand new to coding or eager to level up.

Black Kids Code(Girls) Windsor - Designing For Real Users

Date: Saturday, May 30
Time: 11:00 am – 3:00 pm
Location: University of Windsor
Tickets: Free
Summary: Join us for an exciting workshop designed just for girls aged 8-17. Whether they’re brand new to coding or eager to level up their skills.

Duff-Bâby House – Open Days

Date: Saturday, May 30
Time: 12:00 pm
Location: Duff-Baby House
Summary: Following extensive restoration work by the Ontario Heritage Trust and the installation of new exhibits the Duff-Bâby House is ready to welcome visitors back

WSO Guild Concerto Scholarship Competition

Date: Saturday, May 30
Time: 1:00 pm
Location: School of Creative Arts
Summary: Experience an inspiring afternoon of live classical music as talented young performers from the Windsor Symphony Youth Orchestra compete in the WSO Guild Concerto Scholarship Competition.

Sonata Music Adventures in Concert

Date: Saturday, May 30
Time: 2:00 pm – 3:00 pm
Location: Capitol Theatre Windsor
Tickets: Free
Summary: Join your favorite YouTube teachers—Miss Brianna, Miss Alyssa, Miss Ruby, and Miss Sam—for a fun-filled, family-friendly musical adventure! Follow Sunny as they play games, solve clues, and explore all things music

Funny to be HERE: An afternoon comedy showcase at WindsorEats

Date: Saturday, May 30
Time: 3:30 pm
Location: WindsorEats
Tickets: $15
Summary: For the first time in over a year, Jen Richardson is back at WindsorEats producing some of the most fun comedy shows in town. Oh how much has changed!

Wolfhead Birthday Bash Parking Lot Party

Date: Saturday, May 30
Time: 5:00 pm
Location: Wolfhead Distillery
Summary: Celebrate a decade of Wolfhead Distillery!

Five Course Plated Seafood Dinner

Date: Saturday, May 30
Time: 6:00 pm
Location: Chrysler Theatre
Tickets: $89+taxes & fees Call the box office at 519-252-6579 to purchase tickets! Reserved tables for groups of 6 or more.
Summary: St. Clair College Centre for the Arts Presents: Seafood Dinner and Music by Pianist Ian Smith.

IRL Season 3 Finals Night

Date: Saturday, May 30
Time: 7:00 pm
Location: Glenwood United Church
Tickets: $20
Summary: After four-weeks of fun, friendly, intense, and hilarious competition, FIVE TEAMS of improvisors from Windsor’s IRL – Improv Recreation League are ready for the final face-off!

Frank and Cos: Live in your Neighbourhood

Date: Saturday, May 30
Time: 8:00 pm
Location: Chrysler Theatre
Tickets: $60.00+taxes & fees
Summary: Blue Shirt Entertainment Presents: Frank and Cos in your “neighbourhood” for an unforgettable night of laughter as Frank Spadone and Cosimo Tucci bring their hilarious sketches to life, live and in-person.

Frozenbrick Productions Presents: The Big And Tall Comedy Tour

Date: Saturday, May 30
Time: 8:00 pm
Location: Walkerville Brewery
Summary: Big & Tall Comedy Tour is a high-energy stand-up showcase featuring CJ Erwin, Billy Squires, Jonny P, Tim Reaburn, and Curtis Coleman!

Electro on Erie

Date: Saturday, May 30
Time: 9:00 pm
Location: Erie St GastroPub
Summary: Electro lounge beats all night long with resident DJ, Greg Gnyp + new DJs every week.

Heimat Sunday Brunch Buffets

Date: Sunday, May 31
Time: 10:30 am – 2:30 pm
Location: Heimat
Summary: A whole spread of all the breakfast and lunch foods you could imagine with some of Heimat’s speciality food items!

Allison Brown & Mike Houston Uncorked Weekends at Pelee Island Winery

Date: Sunday, May 31
Time: 12:30 pm
Location: Pelee Island Winery
Tickets: Free
Summary: Join us for some local wine and pizza on the pavilion patio to kick off the summer with some fun music!

Essex County Sourdough Championship

Date: Sunday, May 31
Time: 12:30 pm – 3:00 pm
Location: WindsorEats Food Hall
Tickets: $5.00 – $30.00
Summary: Submit your best sourdough loaf and take part in the Essex County Sourdough Championship celebrating the craft of naturally leavened bread.

Airmails for Autism: Charity Cornhole Tournament

Date: Sunday, May 31
Time: 1:00 pm
Location: GL Heritage Brewing Company
Summary: Get ready to toss some bags for a great cause!

Sunday Sounds At Oxley Estate Winery

Date: Sunday, May 31
Time: 1:00 pm
Location: Oxley Estate Winery
Summary: Join us every Sunday all summer long for live music, great food and wine, and good company right here on the estate.

Windsor Jewish Film Festival

Date: Sunday, May 31 – Thursday, June 04
Time: 1:00 pm
Location: Capitol Theatre
Summary: Celebrate powerful Jewish voices and storytelling at the Windsor Jewish Film Festival—a multi-day spring event hosted at the beautiful Capitol Theatre in downtown Windsor. See website for movie list and showtimes.

LaSalle Night Markets

Date: Sunday, May 31
Time: 4:00 pm
Location: LaSalle Civic Centre
Summary: The LaSalle Night Markets are lively and feature talented local artisans and crafters, farm-to-table local produce, delicious food vendors, amazing merchant consultants and local businesses, exhibiting their handmade and handcrafted products.

Howl at The Moon Dinner Series

Date: Sunday, May 31
Time: 5:00 pm
Location: Oxley Estate Winery
Summary: Experience the magic of a full moon night in the heart of Essex County wine country.

Tour Di Via Italia

Date: Sunday, May 31
Time: 5:45 pm
Location: Via Italia
Summary: Watch racers from all over North America compete for the largest prize purse in Ontario. Race Categories and Start Times: C 5:45pm (30-40 mins) B: 6:30pm (40-60mins) A: 7:15pm (60-80mins) Race times increase as daylight does and slight decrease last two races Please see the website for race rules and registration costs.

Jazz Night Brewery

Date: Sunday, May 31
Time: 6:00 pm
Location: Walkerville Brewery
Summary: Join us on the last Sunday of the month from 6-9PM to enjoy some silky-smooth live jazz by The Coffee House Combo!

Big & Tall Comedy Tour - At Walkerville Brewery

Date: Sunday, May 31
Time: 8:00 pm – 10:30 pm
Location: Walkerville Brewery
Tickets: $20.00 – $25.00
Summary: Featuring Comics Seen on Apple TV, CBC, and Prime Video

Le-Pore, The Merrier! A Birthday Drag Show

Date: Sunday, May 31
Time: 8:00 pm – 11:00 pm
Location: Chapter Two Brewing Company
Tickets: $10.00
Summary: Join us as we celebrate Angelina LePore’s birthday with a night of fun and fabulous drag!

Mark Debonis Live Comedy At Tipsy Toucan (May 30Th)

Date: Sunday, May 31
Time: 8:00 pm – 9:30 pm
Location: The Tipsy Toucan
Tickets: $22.00
Summary: Windsor! Nonstop laughs every Saturday—pro stand-up with nationwide touring headliners!

Canada Day Guide

Date: Monday, June 01 – Wednesday, July 01
Summary: The 2026 Canada Day Guide has been released! Check the website and make plans for the festivities on July 1st!

• Amherstburg Canada Day 5k
• Canada Day At The Park House Museum
• Windsor Canada Day Parade
• Canada Day Celebration – Tecumseh’s Backyard Party
• Canada Day in Kingsville!

Lakeshore Friday and Saturday Classes + Lakeshore Crew

Date: Tuesday, June 02
Time: 6:30 pm
Location: Chrysler Theatre
Tickets: Boxes - $40.00 Section A - $38.00 Section B & Balcony AA-DD - $33.00 Section C & Balcony EE-KK - $30.00
Summary: Pure Academy Presents:

Open Mic at The Grovedale

Date: Tuesday, June 02
Time: 7:00 pm
Location: The Grovedale
Summary: Put your talents up to the mic at Open Mic at The Grovedale!

Phogheads Comedy Showcase

Date: Tuesday, June 02
Time: 8:30 pm
Location: Phog Lounge
Tickets: Free
Summary: Looking for something to do Tuesday night? Skip the scrolling and come laugh.