Windsor’s settling into that stretch where something’s happening almost every day.

From live shows and comedy to markets, celebrations, and Mother’s Day events, there’s plenty of reasons to get out and make the most of the week.

May 7 – May 14
Here’s what’s worth checking out around Windsor.

Stand-up, roasts, and showcases guaranteed to keep the laughs coming.

😂 May 29 – Mom Said Duck
7:00 PM | Capitol Theatre
Moms—this is your Mother’s Day gift.
A high-energy, interactive comedy show filled with laughs, surprises, and crowd-favourite local giveaways. (Dads are welcome too.)

Skip the flowers—give her a night out she’ll actually remember.
A fun, relatable comedy night for parents featuring Jill Moysiuk and special guest Drae. From parenting chaos to everyday struggles, expect real-life stories, sharp humor, giveaways, and a lively atmosphere with a cash bar.

More Info

😂 May 9 – The Bridge: Detroit Edition Live Comedy
8:00 PM | The Tipsy Toucan
Windsor Laughs brings a night of nonstop laughs as Detroit comedian Josh Adams crosses the border with special guests for a high-energy comedy showcase.

😂 May 12 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Phog Lounge
Skip the scrolling and enjoy a night of live stand-up comedy in downtown Windsor.

Late Nights, Loud Beats, and Dark Alternative Vibes Taking Over Windsor.

🎶 May 7 – Destroyer (Solo) Live at Meteor
7:30 PM | Meteor
Experience an intimate evening of music as Destroyer (led by Dan Bejar) brings poetic lyricism and genre-blending soundscapes to the stage. Opening the night is Fortunato Durutti Marinetti, known for a rich, literary songwriting style that sets the tone for an unforgettable show.

🎭 May 8-9-10 – Windsor Light Presents Frozen
7:30 PM | St. Clair College Centre for the Arts
Windsor Light Music Theatre brings Disney’s Frozen to life in a dazzling stage production filled with unforgettable songs, stunning choreography, and breathtaking visuals.

🎭 May 8-9-10 – ACT Presents: Six: Teen Edition
7:30 PM | The Capitol Theatre
History meets pop concert in this high-energy musical where Henry VIII’s six wives remix their stories into a bold celebration of strength, sisterhood, and survival.

🎤 May 8 – Sail Away with Remedy
8:00 PM | The Barbershop Bar
Join The House of Cures for a heartfelt farewell celebration honouring Remedy Hosted by Angelina Lepore and Hudson Bae, this one-night-only event features a powerful lineup including Remedy, Airress, Macoochi Sweets.

🎧 May 8 – Rocking the Cherry Rock Lounge (Twitch)
10:00 PM | Cherry Rock Lounge
Twitch brings their “Ultimate Hard Rock Party Band” experience to Windsor for a high-energy night of 80s and 90s rock party anthems.

🎶 May 9 – Crossroads Live at the International Hotel
8:00 PM | International Hotel, Leamington
The Crossroads Band returns for another high-energy night of live music 🎸 Enjoy a journey through classic rock hits from the 1960s to today.

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

🎸 May 9 – Hysteria: Tribute to Def Leppard
9:00 PM | Cherry Rock Lounge
Get ready for a night of classic arena rock as Hysteria brings the iconic sound of Def Leppard to life.

🎶 May 12 – One Leg One Eye + Efrim Manuel Menuck Live
7:00 PM | Meteor
Experience an immersive night of experimental sound as One Leg One Eye joins Efrim Manuel Menuck on stage.

⭐ 4.4 | 804 Erie St E

Mezzo Ristorante & Lounge is an award-winning Italian fine dining restaurant in Windsor’s historic Via Italia district, known for its blend of classic and modern Italian cuisine. Designed as a mix of elegant dining room and relaxed lounge, Mezzo offers a stylish atmosphere with patio seating, live music, and a private event space for special occasions. It has earned multiple awards for best Italian and fine dining in Windsor and is also recognized for its strong community involvement, including annual charity initiatives and local support programs.

Whether you’d rather celebrate the professionals retreat or celebrate Windsor’s Birthday, enjoy these events!.

🎉 May 9 – Windsor’s 134th Birthday Celebration
11:30 AM – 2:30 PM | City Hall Square West, Windsor
The City of Windsor invites the community to celebrate Windsor’s 134th birthday at City Hall Square 🎂 Enjoy a festive, family-friendly afternoon filled with games, interactive activities, and community spirit right in the heart of downtown

🌸 May 10 – Mother’s Day Brunch Cruise
11:30 AM - 1:30 PM
Enjoy a special Mother’s Day celebration with a scenic brunch and sightseeing tour on the Detroit River. Treat Mom to a delicious spread featuring herb roasted chicken, pancakes, frittata, pasta, desserts, and more—plus a complimentary mimosa and swag bag just for her

Enjoy markets, shows, fashion at Windsor.

🛍️ May 8 – Sip & Thrift Vintage Market
5:00 PM | WindsorEats Food Hall
Part vintage market, part night market — all vibes. Sip, shop, and discover thrifted gems, handmade treasures, and one-of-a-kind finds.

🎭 May 8 – ACT Presents: The Price of Freedom
7:30 PM | The Hatch Studio Theatre at the Jackman Dramatic Art Centre
A powerful original Canadian play exploring the story of John Anderson, a freedom seeker whose landmark extradition case shaped history.

🚶‍♀️ May 9 – WE Walk for HER
9:00 AM | Malden Park Visitor Centre
Join Windsor Life Centre’s annual spring fundraiser supporting women overcoming addiction and rebuilding their lives. The morning includes coffee and snacks, a guided stretch, a community walk, and a Meaningful Market.

🌿 May 9 – LaSalle Horticultural Plant Sale
9:00 AM – 2:00 PM | St. Andrew's Anglican Parish
Join the largest plant sale in LaSalle featuring a wide selection of plants for gardeners of all levels.

✍️ May 9 – Creative Writing Circle
4:00 PM | Windsor Public Library-Central Branch
Are you a writer? Come share your work and connect with fellow writers in a welcoming, supportive environment 📚

🥕 May 9 – Downtown Windsor Farmers’ Market
9:00 AM – 2:00 PM | Pelissier Street
At the Downtown Windsor Farmers’ Market you’ll find farm fresh fruit, vegetables, produce, and unique artisan food products from the best the region has to offer.

🌿 May 9 – Hike 42: A Wildflower Discovery
10:00 AM – 1:30 PM | North 42 Degrees Estate Winery
Join a guided three-mile forest hike through a stunning 40-acre Carolinian forest at North 42 Degrees Estate Winery 🌸 Explore vibrant spring wildflowers like trilliums, spring beauties, and trout lilies.

🌸 May 9 – A Taste of Spring: Flower Preserves Course
Park House Museum
Feeling jelly? Learn how to create beautiful and delicious preserves using edible flowers in this hands-on spring workshop 🌼.

🎨 May 10 – Weekends in the Studio: Breath and Blooms
1:00 PM – 4:00 PM | Art Windsor-Essex
Drop in for a fun, family-friendly art activity led by artist Suela Prendi.

Enjoy Mother’s Day celebrations with us!

🌼 May 8 – Mother’s Day Stroll the Street
6:00 PM – 8:30 PM | Notre Dame Street
Celebrate the special women in your life with an evening of shopping, dining, and live entertainment 🌷 Stroll through eight vibrant blocks filled with local businesses, music, and activities, all set in a charming lakeside community atmosphere.

💐 May 9 – 5th Annual All About Mom Mother’s Day Market
10:00 AM | AMA Sportsmen Association
Celebrate Mother’s Day by shopping from over 40 local vendors offering handmade goods, crafts, and unique gifts.

🎁 May 9 – Mother’s Day Vendor Market
10:00 AM | LaSalle Event Centre
Celebrate Mom at this special Mother’s Day Market featuring local vendors, handmade gifts, and unique treasures.

🎨 May 9 – Weekends in the Studio: Mother’s Day Bouquets with Nora Harvey
1:00 PM – 4:00 PM | Art Windsor-Essex
Join artist educator Nora Harvey for a hands-on, spring-inspired studio activity.

🎀 May 9 – Mother’s Day Market
10:00 AM | Kingsville Lakeside Park Pavilion
Treat Mom (or yourself) to a delightful shopping experience featuring 35 local vendors offering handmade gifts, vintage teacup candles and sweet treats like unique cronuts.

🥧 May 9 – Butter Tart Festival & Mother’s Day Market
10:00 AM | 1039 Lakeshore Road 103, Maidstone, Ontario
Celebrate Mother’s Day with a sweet twist at the Butter Tart Festival & Market featuring local vendors, handmade goods, and plenty of delicious butter tarts.

🎁 May 9 – Morning For Mom Spring Market
9:00 AM – 12:00 PM | Team Goran RE/MAX Care Realty Courtyard
Treat Mom (or yourself) to a beautiful morning celebrating community and local talent 🌼.

🧁 May 9 – Denver’s Homestead Butter Tart Festival
10:00 AM – 4:00 PM | Denver’s Homestead
Celebrate Mother’s Day weekend at the Butter Tart Festival. Explore a homestead filled with bakers and makers offering fresh, locally made butter tarts along with a vendor market perfect for shopping gifts for mom.

🌷 May 10 – Mother’s Day Brunch
11:00 AM | St. Clair College Centre for the Arts
Celebrate Mom (or a special mother figure) with a delicious brunch in the Alumni Skyline Ballroom 💕 Enjoy a wide selection of hot and cold dishes, plus a buffet full of sweet treats sure to impress.

Enjoy May special events in Windsor.

👻 May 9 – Ghost Tours in Sandwich Town
7:30 PM | Sandwich Brewing Co.
Start your evening with a complimentary drink at Sandwich Brewing Co. 🍺 before heading out on a guided walking tour through historic Sandwich Town.

♟️ May 12 – Chapter Two Brewing Company Chess Club
Evening | Chapter Two Brewing Company
Join us for a casual night of chess, great drinks, and friendly competition.

👗 May 13 – Windsor Symphony Orchestra Guild Spring Fantasy Fashion Show
11:00 AM | Beach Grove Golf & Country Club
Enjoy an elegant afternoon of fashion, food, and community at this special luncheon and runway event.

🍽️ May 13 – Amherstburg’s Battle of the Hors D’Oeuvres
6:00 PM – 9:00 PM | Downtown Amherstburg
Savour history one bite at a time at this delicious tasting event in Downtown Amherstburg.

👻 May 13 – Wicked Wednesdays: Haunted Heritage Tours (Summer Edition)
8:00 PM – 9:00 PM | Canadian Transportation Museum & Heritage Village
Join the team at Canadian Transportation Museum & Heritage Village for a spooky evening exploring local history through guided haunted heritage tours.

That’s what’s happening around Windsor this week. Whether you’re planning something special or just seeing where the days take you, there’s no shortage of things to do.

We’ll be back next week with more around the city.
— Windsor Pulse