Windsor’s getting busier by the day, and this week’s lineup proves it.

From live theatre and comedy nights to outdoor markets, concerts, fireworks, and community celebrations, there’s something happening across the city almost every night this week.

May 14 – May 21

Here’s what’s worth checking out 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
Moms—this is your sign to plan the night out already.
Mom Said Duck is a live comedy experience packed with relatable parenting chaos, audience interaction, local giveaways, and the kind of laughs moms never get enough of.
Wine. Laughs. No kids.

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

More Info

😂 May 15 – Stand-Up Comedian Mo Amer
8:00 PM | The Colosseum at Caesars Windsor
Mo Amer brings his internationally acclaimed stand-up comedy to Caesars Windsor for one unforgettable night.

😂 May 16 – Leo Dufour LIVE Comedy At Tipsy Toucan
8:00 PM | The Tipsy Toucan
WINDSOR LAUGHS PRESENTS: Leo Dufour, founder of Windsor’s iconic Komedy Korner, returns to Ottawa Street for a night of high-energy laughs, quick wit, and classic storytelling.

😂 May 19 – 519 Day Comedy Show
8:00 PM – 10:00 PM | WindsorEats Food Hall
Celebrate 519 Day with a night of local stand-up comedy featuring Windsor comics bringing high-energy sets, real material, and a no-fluff lineup.

🎤 May 19 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Phog Lounge
A weekly stand-up comedy showcase featuring a mix of new comics and experienced performers, all delivering live sets in a laid-back downtown setting.

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 15–17 – The Prince of Egypt
Various Showtimes | The Capitol Theatre
Experience the sweeping epic musical The Prince of Egypt, featuring music and lyrics by Stephen Schwartz, including the Academy Award-winning song “When You Believe.”

🎶 May 16–17 – Techno on Tap: A Walkerville Brewery Experience
8:00 PM – 1:00 AM | Walkerville Brewery
SOTC Productions teams up with Walkerville Brewery for two nights of progressive house, melodic techno, and peak-time techno featuring Baran Acar, Ex Libris, Petch, Tyler Johnston, and Portland artist Pleasant Hiss.

🎧 May 16 – Electro on Erie
9:00 PM till late | Erie St GastroPub
Enjoy electro lounge beats all night long with resident DJ Greg Gnyp and rotating guest DJs each week.

🎶 May 17 – Summer Sundays with Cherry Rock Lounge & 89X
7:30 PM – 10:00 PM | Cherry Rock Lounge
Keep the weekend going with Summer Sundays at Cherry Rock Lounge featuring live music, cold drinks, and upbeat summer vibes in partnership with 89X.

🎼 May 17 – Music from China
3:00 PM – 4:00 PM | Mackenzie Hall Cultural Centre
Enjoy an afternoon of traditional Chinese folk music presented by Windsor Multicultural Concerts, featuring performances.

🍷 May 17 – Sunday Sounds at Oxley Estate Winery
1:00 PM – 5:00 PM | Oxley Estate Winery
Kick off the summer Sunday music series with live performance by Chris Bollister alongside great food, wine, and relaxed vineyard vibes.

⭐ 4.4 | 333 Riverside Dr. W

The River Room Restaurant is Windsor’s newest Mediterranean dining spot, located in the DoubleTree and Best Western hotels downtown with sweeping views of the Detroit skyline. The menu reflects global culinary experience, featuring dishes like bacon-wrapped date pinchos, signature seafood specialties such as Pesce Alla Acqua Pazza, and house-made desserts like tiramisu, all served in a modern, relaxed atmosphere with attentive service and a strong focus on flavour and presentation.

Whether you’d rather celebrate the Fireworks or have fun at the fair, enjoy them!!

🎆 May 16 – 2026 Victoria’s Fireworks
5:30 PM | Green Acres Optimist Park
Come out and enjoy live music while treating yourself to something delicious from local vendors as you relax and soak up the atmosphere before the beautiful Victoria Day fireworks display.

🪯 May 17 – Khalsa Day Parade (Nagar Kirtan)
11:00 AM – 4:00 PM | Riverfront Festival Plaza
Celebrate faith, culture, and community at the annual Windsor Sikh Khalsa Day Parade featuring a vibrant Nagar Kirtan procession, cultural displays, and free food Langar meals for all attendees.

🍸 May 17 – Golden Girls Pub Crawl
12:00 PM – 4:30 PM | WindsorEats Food Hall
Dress up as Dorothy, Sophia, Rose, or Blanche (or full 1980s Miami retiree glam) for a themed pub crawl across multiple venues starting at WindsorEats Food Hall. Expect themed cocktails, costume contests, interactive stops, a DJ finale, and a group attempt at a “Golden Girls” record.

🎡 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.

Enjoy markets, shows, fashion at Windsor.

🎭 May 15 – 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, a freedom seeker whose extradition case became a major legal battle tied to the Underground Railroad and the Windsor–Detroit region.

🌽 May 16 – Downtown Windsor Farmers’ Market
9:00 AM – 2:00 PM | Pelissier Street
Enjoy farm fresh fruits, vegetables, artisan foods, crafts vendors, art exhibits, live entertainment, food demonstrations, community booths.

🎨 May 16- Weekends in the Studio! Pool Noodle Printing with Nora Harvey
1:00 PM – 4:00 PM | Art Windsor-Essex
Join artist educator Nora Harvey for a fun, hands-on workshop inspired by Vanessa Dion Fletcher’s BIG Doll exhibition.

🛒 May 16 – Community Garage Sale
9:00 AM | The Salvation Army Windsor Centre of Hope
Explore a community-wide outdoor garage sale featuring 20 vendors offering household items, toys, vintage finds, and hidden treasures.

🚗 May 17 – Yesterday and Today Car Show
11:00 AM – 4:00 PM | Colasanti’s Tropical Gardens
Step back in time with 300+ classic and modern cars, live music, awards, raffles, a crafters’ market, 30+ local vendors, and 10+ food trucks.

🛍️ May 17 – Sunday Farmers Market
11:00 AM – 2:00 PM | WindsorEats Food Hall
Shop local vendors, enjoy fresh food, and relax at the new Sunday Farmers Market at WindsorEats Food Hall.

🧘‍♀️ May 17 – Pilates in the Vineyard
11:00 AM | Paglione Estate Winery
Join Embody Wellness for a relaxing vineyard Pilates experience featuring an all-levels guided class by Leah & Laura followed by a social hour with a spritz, wine, or non-alcoholic sangria.

🎨 May 17 – Birch Trees Landscapes with Suela Prendi
1:00 PM – 4:00 PM | Art Windsor-Essex
Join artist Suela Prendi for a family-friendly drop-in studio activity where participants create birch tree forest scenes using masking tape, acrylic paints, and guided techniques.

🌿 May 20 – Plant Bingo!
6:00 PM – 8:00 PM | The Loose Goose – Walkerville
Join Mack Flash Entertainment and Bouchard Gardens for a fun 8-round bingo night where winners take home hanging flower pots or potted floral arrangements.

🚴 May 20 – Cycle Around the World Presentation & Dedication Ride
6:00 PM | Sportsmans Club
Join cyclist Don Martel for a multimedia presentation sharing stories from his solo global cycling adventures before he begins a 24-hour cross-border charity ride supporting dementia care families in Windsor-Essex and Michigan.

🍣 May 21 – Kōna Sushi Masterclass
6:30 PM | Kōna Lakeshore
Learn the art of sushi-making in this hands-on masterclass where participants will prepare and create their own sushi rolls with guidance from professionals.

Enjoy games, trivia and movie nights in Windsor.

🎬 May 16 – Anaconda Movie Night
7:00 PM | Chrysler Theatre
Catch a special screening of Anaconda, the adventure-horror film following a group of filmmakers whose jungle movie remake turns terrifyingly real when a deadly giant anaconda begins hunting them.

🎶 May 17 – House on Tap: A Walkerville Brewery Experience
8:00 PM – 1:00 AM | Walkerville Brewery
SOTC Productions brings a night of deep house, deep tech minimal, house, and tech house to Walkerville Brewery featuring Designated Jim, Rick Mo, Matty Cants, Detroit artist Britty, and headliner Stirling from London.

🎲 May 18 – Card Board Game Night
5:00 PM – 10:00 PM | Shadowbox Theatre
Drop in for a casual board and card game night featuring everything from strategy and trivia to party and deck-building 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.

That’s your Windsor week at a glance. Whether you’re heading out with friends, spending time with family, or just looking for something different to do, there’s plenty happening around the city this week.

Enjoy the long weekend, explore something local, and we’ll see you next week with more around Windsor.

— Windsor Pulse