What's Happening: Windsor

Power Up In Real Estate – HST New Housing Rebate: What Agents Need To Know

Date: Wednesday, May 20
Time: 11:00 am – 12:30 pm
Location: 12105 Tecumseh Rd E
Tickets: Free
Summary: Join us in person for our Monthly Power Up in Real Estate—a session designed to keep you up to speed on what’s changing in the market.

See Cremation Differently: Lunch & Learn Seminar

Date: Wednesday, May 20
Time: 11:30 am – 1:30 pm
Location: 1700 Tecumseh Rd E
Tickets: Free
Summary: Options, Myths & Questions - Join us to learn from experienced professionals in a friendly and open forum

Plant Bingo!

Date: Wednesday, May 20
Time: 6:00 pm
Location: Loose Goose – Walkerville
Tickets: $40
Summary: On Wednesday May 20, The Loose Goose – Walkerville is teaming up with Mack Flash Entertainment and Bouchard Gardens to give Windsor – Plant Bingo!

519 Day Comedy Show At Windsor Eats

Date: Wednesday, May 20
Time: 8:00 pm – 10:00 pm
Location: WindsorEats Food Hall
Tickets: Free
Summary: Come celebrate the best Windsor has to offer at this FREE Comedy show

Amore & Applause

Date: Thursday, May 21
Time: 4:30 pm
Location: Mezzo Ristorante & Lounge
Summary: Step into your perfect night out at Mezzo. We’re proud to introduce Amore & Applause

Windsor - OPP Shuttle Run & Information Session

Date: Thursday, May 21 – Friday, May 22
Time: 6:00 pm – 9:00 pm
Location: St. Clair College Main (South ) Windsor Campus
Tickets: Free
Summary: The OPP is pleased to invite you to attend and try the 20m Leger Shuttle Run!

Kona Sushi Masterclass

Date: Thursday, May 21
Time: 6:30 pm
Location: Kona Lakeshore
Summary: Have you always wished to learn how to make your own sushi? Know is your chance with these professional classes that teach you everything you need to know!

D.B Presents Scale The System Tour With Locksmith & Goontown & Kahdyn

Date: Thursday, May 21 – Friday, May 22
Time: 7:00 pm – 12:00 am
Location: Phog Lounge
Tickets: $30.00
Summary: High energy night of real bars, live grit, and community locals and legends sharing one stage, one culture.

Perfect Pouring Dinner: Nostalgic Carnival Night

Date: Thursday, May 21
Time: 7:00 pm
Location: Banded Goose Brewing Co.
Summary: Check out the Perfect Pouring Dinner at Banded Goose!

George Thorogood & The Destroyers - The Baddest Show On Earth

Date: Thursday, May 21
Time: 7:30 pm
Location: The Colosseum at Caesars Windsor
Summary: Be there when George Thorogood & The Destroyers hit The Colosseum stage with special guest The Marshall Tucker Band on Thursday, May 21 at 8 PM.

178th Leamington Fair

Date: Thursday, May 21 – Sunday, May 24
Time: 8:00 pm
Location: Leamington Fairgrounds
Summary: The Leamington Fair is back with rides, live shows, midway games, fair food, and classic family fun for everyone!

See website for hours and ticket prices.

2026 Speedo Canadian Masters Swimming Championship

Date: Friday, May 22 – Sunday, May 24
Time: 9:00 am
Location: Windsor International Aquatic and Training Centre
Summary: The 2026 Speedo Canadian Masters Swimming Championships takes over the Windsor International Aquatic and Training Centre!

Sessions are from 9:00-12:00 and 2:00-5:00

The WIATC is one of the best pools in Ontario. Come out and cheer on the swimmers!

If you have an interest in swim competitively, contact the The Windsor Aquatic Club. They have competitive programs for every age group.

Windsor Rib and Beer Festival

Date: Friday, May 22 – Sunday, May 24
Time: 4:00 pm
Location: Riverfront Festival Plaza
Summary: The Northern Heats Rib and Beer Fest is back for another delicious weekend at Riverfront Festival Plaza!

• FRIDAY: 4pm – 11pm
• SATURDAY: 12pm – 11pm
• SUNDAY: 12pm – 8pm

The Prince of Egypt

Date: Friday, May 22 – Sunday, May 24
Time: 7:00 pm
Location: The Capitol Theatre
Summary: The Prince of Egypt is a sweeping epic musical featuring music and lyrics by Grammy and Academy Award winner Stephen Schwartz, a book by Philip LaZebnik, and ten new songs written by Schwartz in addition to five songs from the original DreamWorks Animation film.

ACT Presents: The Price of Freedom

Date: Friday, May 22
Time: 7:30 pm
Location: Hatch Studio Theatre
Tickets: $20 – $30
Summary: Arts Collective Theatre presents The Price of Freedom, a powerful original Canadian play exploring the story of John Anderson, a freedom seeker whose extradition case became one of the most widely debated legal battles in Canadian history.

WSO Chorus: Fauré Requiem

Date: Friday, May 22
Time: 7:30 pm
Location: All Saints’ Anglican Church
Summary: An uplifting evening of choral music offers a moving and reflective experience that brings together timeless sacred works performed with beauty and emotional depth.

Dark Sky Nights – Point Pelee National Park

Date: Saturday, May 23
Time: 5:00 am – 11:59 pm
Location: Point Pelee National Park
Summary: Explore the park after dark and experience the dark skies of Point Pelee National Park.

Downtown Windsor Farmers’ Market

Date: Saturday, May 23
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.

Erie Street GastroPub Block Party

Date: Saturday, May 23 – Sunday, May 24
Time: 10:00 am – 11:00 pm
Location: Erie St GastroPub
Summary: 5 Weekends of Music with Great Food, Patio and Drinks, extended patio and festival. Full details of schedule and entertainers.

Saturday, 10:00 am to 11:00 pm, and Sunday, 8:00 am to 10:00 pm

Essex County in the War of 1812 Re-enactment

Date: Saturday, May 23
Time: 10:00 am – 4:00 pm
Location: Maidstone Bicentennial Museum
Tickets: $8
Summary: See history come alive at the War of 1812 period re-enactment with participants from Fort Malden, Provincial Marine Amherstburg, Voyageur, and others.

Hike 42 – A Wildflower Discovery

Date: Saturday, May 23
Time: 10:00 am
Location: North 42 Degrees Estate Winery
Summary: You’ll embark on a guided three-mile hike, complete with wine tasting and a gourmet camp-style lunch crafted from local ingredients by our Culinary team, prepared fireside.

A Decade of Distilling | Complimentary Guided Tours at Wolfhead

Date: Saturday, May 23
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.

Concert - Saturday Recreational Classes

Date: Saturday, May 23
Time: 11:00 am
Location: Chrysler Theatre
Tickets: Main Floor: $33+taxes & fees Balcony: $30+taxes & fees Boxes: $45+taxes & fees
Summary: Dance Barre Presents: Concert 1 at 11:00 am and Concert 2 at 6:00 pm

Nostalgic Book Fair

Date: Saturday, May 23
Time: 12:00 pm
Location: Walkerville Brewery
Summary: Remember that nostalgic book fair feeling? We’re bringing it back … and this time you’ve got adult money! Join us on Saturday, May 23rd from 12-5 PM at Walkerville Brewery for an afternoon filled with all your favorite book fair vibes.

Country Landscape Kids Pencil Drawing Class

Date: Saturday, May 23
Time: 1:00 pm – 2:00 pm
Location: Expressive Brush Art Studio
Tickets: $15.00
Summary: Learn to sketch a beautiful country landscape while exploring perspective, shading, and pencil techniques.

The Hydroponic Experience: A Hands-On Food Tech Adventure

Date: Saturday, May 23
Time: 5:00 pm – 7:00 pm
Location: Cangro Agrifoods Inc.
Tickets: $30.00
Summary: Curious about how food can be grown without soil? Join us for an exciting and interactive Hydroponic Experience!

90’s Dance Cruise

Date: Saturday, May 23
Time: 6:00 pm
Location: Windsor Premier Cruises
Tickets: $59.99
Summary: Get your kicks on the Macassa Bay for our 1st 90’s Cruise of the season!

A Night in Nashville

Date: Saturday, May 23
Time: 6:00 pm
Location: Pelissier St Parking Garage
Summary: Get ready, Windsor — we’re bringing the heart of Broadway straight to downtown for one unforgettable night.

Square Dance Night

Date: Saturday, May 23 – Sunday, May 24
Time: 7:00 pm – 10:00 pm
Location: Walkerville Brewery
Tickets: $10.00
Summary: Dust off your dancing shoes and join us for a Square Dance at Walkerville Brewery!

Broadway Babes Act Ii

Date: Saturday, May 23
Time: 8:00 pm – 9:30 pm
Location: Chapter Two Brewing Company
Tickets: $7.00
Summary: A night of Drag and Musical Theater starring Aurora Boré Alice, Blossom Kink, Dina Fyre, Kristie Kreme, Bette Tea, & Kristen Mingle.

MagicBox: An Evening of Wonder

Date: Saturday, May 23
Time: 8:00 pm
Location: Shadowbox Theatre
Tickets: $25
Summary: Treat yourself to an unforgettable evening of astounding and awe inspiring close-up magic at The Shadowbox Theatre, featuring four world-class magicians!

Electro on Erie

Date: Saturday, May 23
Time: 9:00 pm
Location: Erie St GastroPub
Summary: Electro lounge beats all night long with resident DJ, Greg Gnyp + new DJs every week.

Walkerville Walking Tour

Date: Sunday, May 24
Time: 10:00 am
Location: Fogolar Furlan Club of Windsor
Summary: Join us on a 3-kilometer, one and a half hour walking tour of Walkerville, one of Windsor’s most distinct and beautiful neighborhoods.

Heimat Sunday Brunch Buffets

Date: Sunday, May 24
Time: 10:30 am – 2:30 pm
Location: Heimat
Tickets: $25.50 Adult/$22.50 Senior/$15.50 Child/Free Under 5
Summary: A whole spread of all the breakfast and lunch foods you could imagine with some of Heimat’s speciality food items!

Campus Community Garden Grand Opening

Date: Sunday, May 24
Time: 11:00 am – 2:00 pm
Location: 372 California Ave
Tickets: Free
Summary: Join us for the Garden Grand Opening and enjoy a fun day with fresh air and good vibes!

Concert - Thursday Recreational Classes

Date: Sunday, May 24
Time: 11:00 am
Location: Chrysler Theatre
Tickets: Main Floor: $33+taxes & fees Balcony: $30+taxes & fees Boxes: $45+taxes & fees
Summary: Dance Barre Presents: Concert 3 at 11:00 am and Concert 4 at 6:00 pm

Rum Runners Tour SOLD OUT

Date: Sunday, May 24
Time: 11:00 am
Location: Rockstar Music Hall
Summary: Hop aboard for a 4-hour thrill ride filled with gangsters, rumrunners, comedy, music, and a lively speakeasy lunch show.

Event Details

The Perfect Pairing – CHV

Date: Sunday, May 24
Time: 12:00 pm
Location: Cooper’s Hawk Vineyards
Summary: Experience the art of wine pairing with a deconstructed charcuterie board – fun, interactive, and delicious!

Sunday Sounds At Oxley Estate Winery

Date: Sunday, May 24
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.

Weekends in the Studio! Neurographic Art with Suela Prendi

Date: Sunday, May 24
Time: 1:00 pm
Location: Art Windsor Essex
Summary: Join us for a fun, family-friendly drop-in studio activity this weekend at the gallery!

Water Sounds

Date: Sunday, May 24
Time: 2:00 pm
Location: John R. Park Homestead
Summary: Join 4th Wall Music in collaboration with ERCA for our concert, “WATER SOUNDS”. Our latest nature awareness concert exploring the sounds, movement and presence of water.

Windsor City Bus Tour – Where Canada Begins

Date: Sunday, May 24
Time: 2:00 pm
Location: Windsor International Transit Terminal
Summary: The Windsor City Bus Tour: Where Canada Begins is a two-hour, guided experience that brings the city’s most fascinating stories, landmarks, and viewpoints to life—right from the comfort of your seat.

Bake Club At Windsor Eats | May Flowers

Date: Sunday, May 24
Time: 3:00 pm – 5:00 pm
Location: 400 Erie St E
Tickets: $15.00
Summary: Thank gosh for May flowers! It's time to bask in the beauty that is spring blossoms & blooms! I know, florals for spring... GROUNDBREAKING!

Flowers: A Tribute To Prince (Windsor, Ontario, Canada)

Date: Sunday, May 24 – Monday, May 25
Time: 7:00 pm – 9:30 pm
Location: Walkerville Brewery
Tickets: $25.00 USD
Summary: Windsor, Ontario!! Get ready to groove and celebrate Prince’s iconic hits live and in person for FLOWERS: a Tribute to Prince!

Hannah Lawrence Live Comedy At Tipsy Toucan (May 23Rd)

Date: Sunday, May 24
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!

Expendable Youth And Brain Stew At The Cherry Rock Lounge

Date: Sunday, May 24
Time: 10:00 pm – 11:59 pm
Location: The Cherry Rock Lounge
Tickets: $10.00
Summary: We’ve decided to drop a limited amount of discounted presale tickets. Grab them while you can!

Chapter Two Brewing Company Chess Club

Date: Tuesday, May 26
Time: 12:00 am
Location: Chapter Two Brewing Company
Summary: In the new year we are introducing a new club: The official Chapter Two Chess Club.

Phogheads Comedy Showcase

Date: Tuesday, May 26
Time: 8:30 pm
Location: Phog Lounge
Tickets: Free
Summary: Looking for something to do Tuesday night? Skip the scrolling and come laugh.