Windsor-Essex is heading into another packed week of summer energy.

From live concerts and comedy to food festivals, night markets, family events, and waterfront nights out, there’s something happening nearly every day across the region.

May 28 – June 4
Here’s what’s worth checking out around Windsor this week.

🎨 May 27 – Grand Opening of Windsor Craft Club
12:00 PM – 6:00 PM | 1009 Drouillard Road Unit 2, Windsor

Celebrate Windsor‑Essex’s first multi‑station craft studio! Drop in to explore pottery painting, custom hat design, mosaics, charms, and more. Bring your friends, make something amazing, and join the creative community.

✨ Instagram | Website

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

😂 May 29 – Comedy Night for Parents with Mom Said Duck
7:00 PM | Capitol Theatre Windsor
MOMS—this is your night out. Book the babysitter and join Jill Moysiuk with special guest Dad comedian Drae for a high-energy comedy show packed with relatable parenting chaos, audience interaction, giveaways all night, and nonstop laughs.

😂 May 30 – The Big And Tall Comedy Tour
8:00 PM – 10:30 PM | Walkerville Brewery
Frozenbrick Productions presents The Big & Tall Comedy Tour, a high-energy stand-up comedy showcase featuring CJ Erwin, Billy Squires, Jonny P, Tim Reaburn, and Curtis Coleman—comedians seen on CBC, Apple TV, and Prime Video.

🎭 May 30 – Improv Rec League (IRL) Finals Night – Season 3
7:00 PM | Glenwood United Church
After four weeks of hilarious competition, FIVE teams from Windsor’s Improv Recreation League are facing off one last time in the Season 3 Finals! Expect fast-paced comedy and plenty of audience laughs.

🎭 May 30 – Frank and Cos: Live in Your Neighbourhood
8:00 PM | Chrysler Theatre
Frank Spadone and Cosimo Tucci bring their hit sketch comedy show to Windsor for a night of live, high-energy performances packed with characters, cultural humour, and relatable “neighbourhood” chaos.

😂 May 30 – Mark DeBonis LIVE Comedy
8:00 PM | The Tipsy Toucan
WINDSOR LAUGHS PRESENTS: Mark DeBonis, award-winning Canadian stand-up comedian and actor, brings his sharp, fast-paced comedy to Windsor for one night only.

😂 May 30 – Funny to be HERE: Comedy Showcase
3:30 PM – 5:30 PM | WindsorEats
A high-energy afternoon comedy showcase takes over WindsorEats featuring a stacked lineup of comedians from Windsor, Toronto, and Michigan.

😂 June 2 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Phog Lounge
Phogheads Comedy Showcase brings a weekly night of live stand-up comedy to downtown Windsor, featuring a rotating lineup of new comics and experienced performers.

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.

🎶 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.

🎵 May 30 – Sonata Music Adventures in Concert
2:00 PM | Capitol Theatre Windsor
Join your favorite YouTube music teachers—Miss Brianna, Miss Alyssa, Miss Ruby, and Miss Sam—for a fun, family-friendly musical adventure live on stage!

🎼 May 30 – WSO Guild Concerto Scholarship Competition
1:00 PM | School of Creative Arts
The WSO Guild Concerto Scholarship Competition showcases outstanding young musicians from the Windsor Symphony Youth Orchestra as they perform challenging concerto repertoire in front of a live audience.

🎧 May 30 – Electro on Erie
9:00 PM till late | Erie St GastroPub
Electro on Erie brings a night of nonstop electronic lounge beats with resident DJ Greg Gnyp, plus rotating guest DJs each week.

🎶 May 31 – Allison Brown & Mike Houston LIVE at Pelee Island Winery
12:30 PM – 4:30 PM | Pelee Island Winery, Kingsville
Uncorked Weekends returns with a relaxed afternoon of live music featuring Allison Brown & Mike Houston, performing classic country, bluegrass, folk, and Americana roots music.

🎻 May 31 – Westbound Situation: Classical Meets Bluegrass & Jazz!
4:00 PM | Trinity Lutheran Church
Westbound Situation brings a vibrant, genre-blending performance that fuses classical precision with the improvisational energy of jazz and the drive of bluegrass.

🎷 May 31 – Jazz Night Brewery
6:00 PM – 9:00 PM | Walkerville Brewery
Enjoy a relaxed Sunday evening of smooth live jazz at Walkerville Brewery featuring The Coffee House Combo. This monthly Jazz Night brings laid-back, toe-tapping performances in a cozy taproom atmosphere.

🎤 June 2 – Open Mic at The Grovedale
7:00 PM | The Grovedale
Step up to the mic or sit back and enjoy a night of live, local talent at Open Mic Night at The Grovedale. Hosted by Tina Schroeder, this welcoming community event features musicians, poets, singers, rappers, comedians, and anyone ready to share their talent on stage.

🎤 June 3 – We Three Kings: The Multinational Tribute to Elvis Presley
7:30 PM | Rockstar Music Hall
Experience the music and legacy of Elvis Presley brought to life in We Three Kings, a high-energy tribute concert featuring three award-winning Elvis tribute artists from Germany, the United States, and Canada.

Enjoy special Jewish Film Festival and the Cosmo club!!!

🎬 May 31 – June 4 – Windsor Jewish Film Festival
Capitol Theatre Windsor | Windsor, Ontario
The Windsor Jewish Film Festival is a multi-day celebration of storytelling through cinema, featuring a curated selection of powerful dramas, heartfelt comedies, and thought-provoking documentaries. The festival highlights diverse voices, cultural experiences, and unforgettable narratives from Jewish filmmakers and global perspectives.

💃 June 3 – Cosmo Club: Bridgerton Style
🕔5:00 PM – 8:30 PM | Wolfhead Distillery
Cosmo Club returns for an elegant Bridgerton-inspired girls’ night out at Wolfhead Distillery. This themed social evening features woman-owned vendors, curated cocktails, and light bites, all designed as a midweek escape focused on connection, community, and fun. The highlight of the night is a Bridgerton-style Strauss dance experience presented with Teutonia Club performers in period costume.

Enjoy markets, shows, fashion at Windsor.

🚲 May 29 – Essex Glow Ride
6:00 PM – 8:00 PM | Sadler’s Park, Town of Essex
Join the Essex Glow Ride at Sadler’s Park for a fun, family-friendly evening packed with cycling activities, community events, and glowing bike fun.

🛍️ May 30 – South Walkerville Neighbourhood Yard Sale
10:00 AM – 3:00 PM | South Walkerville, Windsor
South Walkerville residents are hosting a massive neighbourhood-wide yard sale featuring over 30 participating blocks throughout the area.

🎨 May 30 – The Canvas Caravan!
9:30 AM – 1:30 PM | Pelissier Street Parking Garage
The Canvas Caravan brings a fun-filled day of creativity to the “Kids Corner” of the Downtown Windsor Farmers’ Market.

🏃‍♂️May 30 – Pelee Island Winery Half Marathon
Pelee Island Winery | Pelee Island / Kingsville region
The Pelee Island Winery Half Marathon returns for its 12th edition as Canada’s most southern half marathon.

🧺 May 30 – Downtown Windsor Farmers’ Market
Downtown Windsor
The Downtown Windsor Farmers’ Market brings together fresh local produce, artisan food products, crafts, community booths, live entertainment, and family-friendly activities right in the heart of the city.

🛍️ May 31 – LaSalle Night Markets
4:00 PM – 8:00 PM | LaSalle Civic Centre
The LaSalle Night Markets are a vibrant community event featuring local artisans, crafters, farm-to-table produce, food vendors, and small businesses showcasing handmade and handcrafted goods.

🚶 May 31 – IG Wealth Walk for Alzheimer’s (Windsor)
8:30 AM Registration | 10:00 AM Walk Start | Ford Test Track Park
The IG Wealth Walk for Alzheimer’s is a community fundraising walk supporting people living with Alzheimer’s disease and other forms of dementia, along with their families and caregivers.

🌿 June 2 – Community Clean-Up Day (Pollinate Kingsville)
6:00 PM – 7:30 PM | Chrysler Canada Greenway (169 Lansdowne Ave)
The Pollinate Kingsville Committee is inviting community members to take part in a volunteer clean-up initiative focused on keeping Kingsville’s outdoor spaces clean, welcoming, and environmentally healthy.

🏀 June 1 – Skills Development Academy (Windsor Express Basketball)
4:30 PM – 6:00 PM | Riverside Sports Centre
WINDSOR EXPRESS presents its Intermediate/High Performance Skills Development Academy, a high-energy basketball training program for boys and girls ages 10–15 with prior playing experience.

🏀 June 3 – Beginner Skills Development Academy (Windsor Express)
4:30 PM – 6:00 PM | Riverside Sports Centre
The Windsor Express Beginner Skills Development Academy is designed for boys and girls ages 7–12 who are new to basketball and want to build a strong foundation in the game.

🎣 May 30 – Lake St. Clair King of the Lake Walleye Tournament
Stoney Point Sportsmen’s Club | Lakeshore, Ontario
The Lake St. Clair King of the Lake Walleye Tournament is a competitive fishing event bringing anglers together for a full day on the water targeting walleye in Lake St. Clair.

🎯 May 31 – Airmails for Autism: Charity Cornhole Tournament
1:00 PM | GL Heritage Brewing Co., Amherstburg
The “Airmails for Autism” charity cornhole tournament, hosted by Border City Cornhole, is a community-focused fundraising event bringing players together for friendly competition in support of autism awareness.

Enjoy games, trivia and dinner nights in Windsor.

🤠 May 28 – Country Line Dance Night
7:00 PM – 10:00 PM | Walkerville Brewery
WALKERVILLE BREWERY PRESENTS: Country Line Dance Night—an energetic evening of music, movement, and good vibes at Walkerville Brewery.

⛵ May 30 – Opening of the Marina
5:00 PM | Holiday Harbour, LaSalle
Celebrate the official opening of the marina with an evening of great food, live music, and waterfront vibes at Holiday Harbour. Guests can enjoy a pasta dinner followed by live music.

🎶 May 30 – Springtime Harmony Cabaret with the Essex Vocal Express
5:30 PM | Leamington Portuguese Community Club
Celebrate spring with an unforgettable evening of live entertainment, gourmet dining, and world-class four-part a cappella harmony. The Essex Vocal Express returns with a cabaret-style fundraising dinner.

🍽️ May 30 – Five Course Plated Seafood Dinner
6:00 PM | St. Clair College Centre for the Arts
Enjoy an elegant evening featuring a professionally curated five-course seafood dinner overlooking the Detroit River at St. Clair College Centre for the Arts.

🥃 May 30 – A Decade of Distilling | Wolfhead Complimentary Guided Tours
11:00 AM – 3:00 PM | Wolfhead Distillery
Celebrate 10 years of craft distilling with complimentary guided tours at Wolfhead Distillery. Guests are invited to go behind the scenes and explore the production space, learn about the whisky-making process, etc.

🍝 May 30 – Pasta with a Purpose
5:00 PM – 10:00 PM | Royal Canadian Legion
Pasta with a Purpose is a community fundraising dinner supporting The Soup Shack Windsor, an organization that provides food and beverages nightly to individuals who are unhoused or food insecure.

🌕 May 31 – Howl at The Moon Dinner Series
5:00 PM – 8:00 PM | Oxley Estate Winery
The “Howl at the Moon” Dinner Series returns for a magical evening in the heart of Essex County wine country at Oxley Estate Winery.

🎲 June 3 – Game Nights @ Central for Adults
6:30 PM | Windsor Public Library – Central Branch
Join a fun, social evening of tabletop gaming designed for adults. Each month features a different game.

🍟 June 4 – Poutine Feast Windsor
Riverfront Festival Plaza | Riverside at McDougall, Windsor
The Poutine Feast is a four-day food and entertainment festival celebrating Canada’s iconic dish with a creative twist.

That’s your Windsor week at a glance. Whether you’re planning a night out, checking out a local festival, or just looking for something new to do, there’s plenty happening across Windsor-Essex this week.

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