The city’s heading into one of its busiest stretches of the season.

From concerts and comedy to Rib-fest, markets, fairs, and late-night events, Windsor-Essex is packed with things worth getting out for this week.

May 21 – May 28
Here’s what’s happening around Windsor.

Windsor’s comedy scene is bringing nonstop laughs with stand-up showcases, lighting up intimate venues all across the city.

😂 May 29 – Mom Said Duck
7:00 PM | Capitol Theatre
Windsor moms—it’s almost time.
Mom Said Duck takes over the Capitol Theatre next week for one unforgettable night of comedy, crowd interaction, giveaways, and moms-night-out energy.
Grab your girlfriends, book the babysitter, and come laugh with us.

A hilarious parents’ night out with Jill Moysiuk and Dad comedian Drae, packed with relatable parenting chaos and laughs.

More Info

😂 May 23 – Hannah Lawrence LIVE Comedy
8:00 PM | The Tipsy Toucan
WINDSOR LAUGHS PRESENTS: Hannah Lawrence, a Toronto-born stand-up comedian known for appearances brings her high-energy, sharp-witted comedy to Windsor for a night of laughs and live stand-up.

😂 May 26 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Phog Lounge, Windsor
Skip the scrolling and come laugh at the Phogheads Comedy Showcase, a weekly stand-up night featuring a mix of new comics and seasoned performers delivering live comedy.

Windsor’s music scene is stacked this season—from techno nights and live summer DJ parties, there’s a sound for every vibe and every night out.

🎤 June 3 – We Three Kings: Elvis Tribute Show
7:30 PM | Rockstar Music Hall
A high-energy tribute to Elvis Presley featuring Roy LeBlanc, Oliver Steinhoff, and Leo Days. This multinational show covers Elvis’s greatest eras—from early rock ’n’ roll and the ’68 Comeback Special to his iconic Vegas performances.

With a full live band, authentic costumes, and powerful vocals, expect a fun, nostalgic night packed with timeless hits and crowd-pleasing moments.

More Info

🎸 May 21 – George Thorogood and The Destroyers
7:30 PM | The Colosseum At Caesars Windsor
George Thorogood and The Destroyers hit the stage in Windsor for a night of classic rock and blues-driven hits at Caesars Windsor.

🎭 May 22-23-24 – The Prince of Egypt: The Musical
See Description | The Capitol Theatre
The Prince of Egypt is a sweeping epic musical featuring music and lyrics by Stephen Schwartz, including the Academy Award-winning song “When You Believe.”

🎶 May 22 – WSO Chorus: Fauré Requiem
7:30 PM – 9:00 PM | All Saints’ Anglican Church
The Windsor Symphony Orchestra Chorus presents a special evening of choral masterworks.

🎶May 23 – A Night In Nashville
6:00 PM | Pélissier Street Parking Garage
Downtown Windsor brings the energy of Nashville’s Broadway to the city for a high-energy country music night featuring live performances, drinks, and a packed concert-style atmosphere.

🎩 May 23 – MagicBox: An Evening of Wonder
8:00 PM | The Shadowbox Theatre
MagicBox brings an unforgettable night of close-up magic featuring world-class performers Chris Philpott, Eric Bedard, Dreygon, and Johnny New York.

🎤May 24 – Saxappeal Presents: Flowers – A Tribute to Prince
7:00 PM – 9:30 PM | Walkerville Brewery
Get ready for a high-energy tribute celebrating the music of Prince, featuring live performances of his most iconic hits in an electrifying night of funk, soul, and groove at Walkerville Brewery

🎶 May 28 – Cat Clyde with Joe Abbott at Meteor
8:00 PM | Meteor, 138 University Ave. W
An intimate evening of soulful roots music featuring acclaimed Canadian singer-songwriter Cat Clyde for a night of heartfelt songwriting, rich vocals, and emotionally driven live performance.

⭐ 4.5 | 614 Erie St. E
Bacchus Ristorante is all about turning a great meal into a truly memorable experience. Known for its “fabulous dining” approach, it combines elevated Italian-inspired cuisine with a refined and elegant atmosphere that feels both upscale and welcoming. One of the highlights is the beautiful outdoor patio, offering a relaxed yet sophisticated setting for dining in the warmer months. It’s an ideal spot for date nights, celebrations, or simply enjoying a slower, more refined meal with friends and family.

Enjoy the fairs and fests happening in Windsor.

🎡 May 21–24 – 178th Leamington Fair
All Day | Leamington Fairgrounds
The Leamington Fair returns with four days of midway rides, live entertainment, demolition derby action, concerts, agricultural displays, local vendors, fair food, games, and a beer tent.

🍖 May 22–24 – Windsor Ribfest
4:00 PM–11:00 PM (Fri) | 12:00 PM–11:00 PM (Sat) | 12:00 PM–8:00 PM (Sun) | Riverfront Festival Plaza, Riverside at McDougall, Windsor
A weekend full of food, fun, and entertainment featuring Ribfest favourites, live vendors, and family-friendly activities along the Windsor riverfront.

🥨 May 23 – Maifest at the Heimat
5:00 PM | Heimat, 1367 Drouillard Road
Maifest at the Heimat celebrates spring Bavarian-style with traditional German food, authentic Munich-imported beer, live music, and cultural performances.

🏃‍♀️ May 24 – Evolve 5K Rosé
11:00 AM | Paglione Estate Winery, 724 County Road 50 East, Harrow
Celebrate five years of the Evolve 5K Rosé with a community run/walk supporting mental health. Enjoy a scenic 5K course followed by rosé at the finish line, along with pre-run yoga, vendors, prizes, snacks, and a full wellness-focused atmosphere at the winery.

Enjoy markets, shows, fashion at Windsor.

🎭 May 22 – The Price of Freedom
Showtimes vary | The Hatch Studio Theatre at the Jackman Dramatic Art Centre
Arts Collective Theatre presents an original Canadian play exploring the story of John Anderson.

🛍️ May 23 – South Walkerville Neighbourhood Yard Sale
10:00 AM – 3:00 PM | South Walkerville
A massive neighbourhood-wide yard sale featuring over 30 participating blocks across South Walkerville.

📸 May 23 – Nostalgic Photo Booth @ Central Library
4:00 PM | Windsor Public Library – Central Branch
Relive classic mall-style photo booth memories with a modern twist using a professional camera, fun props, and digital photo layouts.

🎉 May 23 – FREE Family Fun Day!!
10:00 AM – 2:00 PM | Farrow Riverside Miracle Park, Windsor
A free community event packed with family-friendly fun featuring local police and fire truck displays, library participation, games, crafts, dancing, and more.

🧺 May 23 – Downtown Windsor Farmers’ Market
Pelissier & Maiden Lane, Downtown Windsor
The Downtown Windsor Farmers’ Market features fresh local produce, farm goods, artisan foods, crafts, and community vendors.

📚 May 23 – Nostalgic Book Fair at Walkerville Brewery
12:00 PM – 5:00 PM | Walkerville Brewery
Bring back the nostalgic school book fair vibe—this time with craft beer.

🎉 May 24 – Erie St GastroPub & Lotus and Lattes Street Festival
10:00 AM | Elsmere Street
A community street festival featuring a full weekend of entertainment, fitness, artisan vendors, food, and activities as part of a series of seasonal street closures supporting local charities and businesses.

🚴‍♀️ May 24 – Community Bike Rodeo!
10:00 AM – 12:00 PM | Families First, 1065 Lauzon Road
Join the Optimist Club of Riverside for a free community bike day featuring safety learning, skill-building, and family-friendly fun for riders of all ages.

♟️ May 26 – Chapter Two Brewing Company Chess Club
Chapter Two Brewing Company
Join a relaxed chess night featuring casual games, friendly competition, and a welcoming atmosphere for all skill levels.

Upcoming sports events in Windsor.

🏊 May 22–24 – 2026 Speedo Canadian Masters Swimming Championships
Windsor International Aquatic and Training Centre
The 2026 Speedo Canadian Masters Swimming Championships bring together 748 athletes from 88 clubs across Canada, the United States, and Great Britain for a high-level competitive swimming event.

🏀 May 25 – Skills Development Academy (Windsor Express Basketball)
4:30-6 PM | Riverside Sports Centre
The Windsor Express Skills Development Academy is a high-performance basketball training program for boys and girls ages 10–15 with prior experience, focused on advanced skill development.

🏀 May 27 – Beginner Skills Development Academy (Windsor Express Basketball)
4:30-6 PM | Riverside Sports Centre
The Windsor Express Beginner Skills Development Academy is a fun and supportive basketball program for boys and girls ages 7–12 who are new to the game, focused on building strong fundamentals including dribbling, passing, shooting, and game awareness.

Enjoy games, trivia and dinner nights in Windsor.

🎲 May 21 – Brews & Board Games at Walkerville Brewery
5:00 PM | Walkerville Brewery
Join Walkerville Brewery and Tabletop Bellhop for an evening of craft beer, bites, and board games.

🍺 May 21 – Perfect Pouring Dinner: Nostalgic Carnival Night
7:00 PM | Banded Goose Brewing Co.
Step into a carnival-inspired tasting experience featuring a chef-driven 4-course menu with nostalgic fair-style dishes like mac & cheese corn dogs, bacon-wrapped chicken lollipops, churro-dogs, and beef slider pairings.

🚢 May 23 – 90’s Dance Cruise
6:00 PM – 10:00 PM | Windsor Premier Cruises (Macassa Bay)
Step aboard for a high-energy 90’s-themed cruise featuring DJ Chino spinning all your favourite throwback hits from the decade.

🍗 May 23 – Chicken Dinner & Historic Sandwich Tales Live Performance
4:30 PM | Bedford United Church
Enjoy a community chicken dinner featuring roasted chicken, mashed potatoes, gravy, vegetables, rolls, dessert, coffee, and tea, followed by a special live historical performance.

🤖 May 27 – Spring Trivia Night Fundraiser (FRC Teams 1229 & 6867)
6:00 PM | St. Nicholas Macedonian Orthodox Church Community Centre,
Support local robotics teams at a community trivia fundraiser hosted by FRC 1229 Tidal Shift and 6875 Amazon Warriors.

That’s your week around Windsor. Whether you’re planning a night out, checking out a local festival, or just looking for something different to do, there’s plenty happening across the city and Essex County this week.

Enjoy the warmer days, support local, and we’ll be back next week with more happening around Windsor.
— Windsor Pulse