Windsor-Essex is embracing the best of summer with a week full of live entertainment, outdoor experiences, community gatherings, and local celebrations.

From music by the waterfront and artisan markets to theatre, comedy, food events, and unique summer activities, there are plenty of reasons to get out and explore the region.

July 16 – July 23

Here’s what’s happening around Windsor-Essex this week.

🎭 July 23, 24, 25 & 26 – Milk Milk Lemonade
July 23–26 | Soiree Space, 628 Monmouth Rd, Windsor

80% clown, 40% sketch, 10% macaroni art, and 22% we haven't learned to do percentages yet, "Milk Milk Lemonade" follows the (class) clowns of Mallowmarsh Elementary as they navigate the snack-time stock exchange, the horrors of health class, and the rough-and-tumble world of indoor recess to answer the age-old question: I know you are but what am I?

More Info

🛍️ July 18 – Colchester Markets
10:00 AM – 3:00 PM | Heritage Colchester, 195 Bagot Street, Colchester, ON

A vibrant community market celebrating local makers, artists, food vendors, and Colchester’s rich heritage. Explore unique handcrafted goods, enjoy delicious treats, take part in historical tours, and connect with local organizations while supporting the restoration of Colchester Schoolhouse #2. 🌿🏡

View More

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.

🎶 July 16 – Live at the Lighthouse
7:00 PM | Mettawas Park
Spend a relaxing summer evening at Live at the Lighthouse, a free outdoor concert series held every Thursday in July and August at the gazebo beside the Kingsville Lighthouse.

🎧 July 18 – Retro Silent Disco
12:00 AM – 12:30 AM | Water’s Edge Event Centre
Dance the night away at the Retro Silent Disco, where Water’s Edge Event Centre transforms into a high-energy dance floor complete with nightclub-style lighting, visual effects, and three live DJs spinning the biggest hits from the 80s, 90s, and 2000s.

🎶 July 18 – Music Onthe42 Summer Concert Series: Rick LaBonte & Band of Brothers
7:30 PM | SUNSET® Amphitheatre, Seacliff Park
Enjoy a summer evening of free live music at Leamington’s Music Onthe42 Summer Concert Series. The night begins with an opening performance by The 519 Band at 7:30 PM, followed by headliners Rick LaBonte & Band of Brothersat 8:30 PM.

🎧 July 18 – Electro on Erie
9:00 PM | Erie St GastroPub
Wrap up your Saturday night at Electro on Erie, where resident DJ Greg Gnyp and a rotating lineup of guest DJs keep the dance floor alive with smooth electronic lounge music and energetic beats.

🍷 July 19 – Uncorked Weekend
12:00 PM – 4:00 PM | Pelee Island Winery
Spend a relaxing summer afternoon at Uncorked Weekend, where live music, award-winning wine, and authentic wood-fired pizza come together in a beautiful vineyard setting.

🎸 July 19 – Sprucewood Shores Summer Music Series Featuring Max Marshall
1:00 PM – 3:00 PM | Sprucewood Shores Estate Winery
Enjoy a relaxing Sunday afternoon by the shores of Lake Erie with live music from Max Marshall as part of the Sprucewood Shores Summer Music Series.

🎶 July 19 – Sunday Sounds at Oxley Estate Winery
1:00 PM – 5:00 PM | Oxley Estate Winery
Spend a relaxing Sunday afternoon at Oxley Estate Winery with live music, delicious food, award-winning wines, and beautiful vineyard views.

🎸 July 19 – Summer Sundays with Cherry Rock Lounge & 89X
7:30 PM – 10:00 PM | Cherry Rock Lounge
End your weekend on a high note at Summer Sundays with Cherry Rock Lounge & 89X. Enjoy an evening of live music, refreshing drinks, and a lively atmosphere as local entertainment keeps the energy going well into the night.

🎶 July 23 – Live at the Lighthouse Featuring Acoustics Unlimited
7:00 PM – 8:30 PM | Mettawas Park Gazebo
Enjoy a relaxing summer evening by the waterfront at Live at the Lighthouse, Kingsville’s free outdoor concert series. On July 23, Acoustics Unlimited takes the stage with a lively mix of classic rock, pop, folk, and country favourites.

🎸 July 23 – Bush Live at The Colosseum
8:00 PM | The Colosseum at Caesars Windsor
Legendary British rock band Bush brings its high-energy live show to The Colosseum at Caesars Windsor, joined by special guest JJ Wilde.

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

😂 July 18 – Eric Johnston: Son of a Bull Comedy Tour
7:00 PM – 10:00 PM | Royal Canadian Legion Branch 403
Enjoy an evening of stand-up comedy as award-winning comedian, bestselling author, and Top 40 Under 40 honouree Eric Johnston brings his Son of a Bull Comedy Tour to Pelee Island.

🎤 July 18 – DIRTBALLS Live Comedy Show
7:30 PM – 9:00 PM | The Tipsy Toucan
Get ready for a night of uncensored laughs as comedians Amish Patel and Gee Gethiga bring their DIRTBALLS live comedy show to Windsor’s only dedicated live comedy club.

😂 July 18 – Standup at Sidelines!
8:00 PM – 9:30 PM | Sidelines Sports Bar & Grill
Enjoy an evening of laughter at Standup at Sidelines!, featuring a talented lineup of comedians from Toronto, Windsor, Detroit, and Ohio.

🎭 July 16-17 – Chrysler Theatre Youth Summer Camp
9:00 AM – 4:00 PM | Chrysler Theatre
Give young performers the chance to shine at the Chrysler Theatre Youth Summer Camp, where participants spend the week developing their singing, dancing, and acting skills on the Chrysler Theatre stage. Led by experienced instructors, the camp features fun games, interactive workshops, performance techniques, and exciting opportunities to build confidence while making new friends.

🎭 July 17 – Park House Museum’s Bridgerton Masquerade Tea
11:00 AM – 5:00 PM | Park House Museum
Step into the elegance of the Regency era at the Bridgerton Masquerade Tea hosted by the historic Park House Museum. Inspired by the beloved Bridgerton series, this enchanting event features afternoon tea, delicious treats, intriguing mystery, and plenty of lively gossip in a beautifully themed setting. Guests are invited to immerse themselves in the charm and sophistication of the occasion, making it a memorable experience for fans of period dramas and afternoon teas alike.

🌶️🎧 July 17–19 – SYNC Festival
Riverfront Festival Plaza
SYNC Festival returns to Riverfront Festival Plaza with house, techno, and dance music. Presented by SOTC Productions, this multi-day event features an exciting lineup of internationally recognized DJs including Will Clarke, Crusy, Sydney Blu, David Lindmer, Paradoks, and Weska, alongside talented regional and local artists.

🦇 July 18 – Bats on the Beach: A Goth Beach Party
9:00 PM | Meteor
Celebrate summer with a dark twist at Bats on the Beach, a unique goth-themed beach party filled with music, dancing, and creative fashion. Guests are encouraged to wear tropical goth outfits, vampire vacation attire, black beachwear, or any spooky summer-inspired look. Enjoy themed cocktails, non-alcoholic drink options, and an energetic soundtrack of goth favourites while soaking up the eerie beach vibes.

🍻 July 19 – GL Heritage Anniversary Party
1:00 PM – 4:00 PM | GL Heritage Brewing Company
Celebrate GL Heritage Brewing Company’s 9th Anniversary with an afternoon of live music, great drinks, and community spirit. Enjoy performances by Adam Butcher and Lauren Victoria under the brewery’s newly built pavilion while relaxing with friends in a welcoming outdoor setting. Whether you're a longtime fan of GL Heritage or visiting for the first time, this anniversary celebration is the perfect opportunity to enjoy local music, craft beer, and a festive summer atmosphere.

Enjoy markets, shows, fashion at Windsor.

🌞 July 17-19 – Amherstburg Open Air Weekends
3:00 PM (Friday) – 8:00 PM (Sunday) | Downtown Amherstburg
Enjoy a lively weekend in downtown Amherstburg with Amherstburg Open Air Weekends, a free community celebration featuring local vendors, shopping, live entertainment, and family-friendly activities.

🎭 July 16–19 – Summer Theatre: Talley’s Folly
Heritage Colchester
Enjoy an intimate theatrical experience with Summer Theatre: Talley’s Folly, presented by the Inspired Acting Lab in partnership with Heritage Colchester.

🎨 July 16 – AWE Summer Nights: Opening Night
5:00 PM – 9:00 PM | Art Windsor Essex
Celebrate the opening of Art Windsor Essex’s summer exhibition season at AWE Summer Nights: Opening Night

🍣 July 16 – Kona Sushi Masterclass
6:30 PM | Kona Lakeshore
Learn the art of sushi making at the Kona Sushi Masterclass, a hands-on culinary experience led by professional instructors. Participants will discover how to prepare sushi rolls, create their own custom rolls, and gain practical techniques they can use at home.

🌳 July 16 – Neighbourhood Nights: Mic Mac Park
6:30 PM – 9:00 PM | Mic Mac Park
Enjoy a fun-filled evening close to home at Neighbourhood Nights, a free community celebration featuring live entertainment, family-friendly activities, and opportunities to connect with neighbours.

🌙 July 17 – Amherstburg Open Air Night Markets
Friday Evening | Downtown Amherstburg
Spend your Friday evening exploring the Amherstburg Open Air Night Markets, where local vendors, live entertainment, delicious food, and handmade treasures come together in a lively outdoor setting.

🛍️ July 18 – Lakeside Market
8:00 AM – 1:00 PM | Atlas Tube Centre
Spend your Saturday morning exploring the Lakeside Market, a vibrant community gathering featuring local farmers, growers, artisans, makers, food vendors, and small businesses.

🥕 July 18 – Downtown Windsor Farmers’ Market
9:00 AM – 2:00 PM | Pelissier Street
Spend your Saturday exploring the Downtown Windsor Farmers’ Market, where you'll find farm-fresh fruits, vegetables, locally grown produce, and a wide variety of artisan food products from across Windsor-Essex.

⚔️ July 18–19 – Living Battlefields: Historical Reenactment
Canadian Transportation Museum & Heritage Village
Step back in time at Living Battlefields, an immersive American Civil War reenactment weekend at the Canadian Transportation Museum & Heritage Village

🌾 July 18 – Farmer’s Market in the Quarry
10:00 AM – 1:00 PM | Stone & Sky at The Quarry
Spend a relaxing Saturday morning at the Farmer’s Market in the Quarry, hosted by Stone & Sky. Browse a selection of local vendors offering fresh produce, handmade goods, and artisan products.

🏡 July 18 – Colchester Markets
10:00 AM – 3:00 PM | Heritage Colchester
Experience the charm of Colchester Markets, a vibrant community market celebrating local creativity, history, and culture in the heart of Colchester’s historic district

🎨 July 18 – Walkerville Art Walk
11:00 AM – 10:00 PM | Walkerville
Spend the day exploring the Walkerville Art Walk, an annual celebration of local art, creativity, and community.

🎬 July 18 – City Cinema Saturdays
11:00 AM – 2:00 PM | Performance Hall of SoCA Armouries
Enjoy a fun-filled Saturday morning at City Cinema Saturdays, a free summer movie series presented in partnership with the Windsor International Film Festival.

🖌️ July 18 – Mousetrap Artist Bazaar
11:00 AM – 6:00 PM | Walkerville Brewery
Discover an incredible showcase of local creativity at the Mousetrap Artist Bazaar, returning as part of the Walkerville Art Walk. This free pop-up market features 18 talented local artists, designers, and makers offering everything from handmade leather goods, ceramics, stained glass, and apparel to illustrations, woodwork, quirky gifts, home décor, and unique collectibles.

🎉 July 18 – Kingsville Block Party: Kids Night
5:00 PM – 10:00 PM | Kingsville Centre
Celebrate summer with family and friends at the Kingsville Block Party – Kids Night, a lively community event filled with fun, food, and entertainment.

✨ July 18 – Dark Skies & Fireflies Night Market
4:00 PM – 10:00 PM | Event Centre at LaSalle Landing
Spend a magical summer evening at the Dark Skies & Fireflies Night Market, featuring more than 40 local vendors, delicious food, live entertainment, and interactive activities for all ages.

🛒 July 19 – Tecumseh Farmers Market
9:00 AM – 1:00 PM | Lacasse Park
Spend your Sunday morning exploring the Tecumseh Farmers Market, where local farmers, artisans, and small businesses come together to showcase the best of the region.

🦉 July 19 – Needle Felted Owl Workshop
10:30 AM – 1:30 PM | John R. Park Homestead
Discover the art of needle felting in this hands-on Needle Felted Owl Workshop, where participants will create their own charming wool owl under the guidance of Maggie from Wollie Wonders by Maggs.

🎨 July 23 – AWE Summer Nights
5:00 PM – 9:00 PM | Art Windsor Essex
Spend a summer evening at AWE Summer Nights, where art, food, and beautiful waterfront views come together in a relaxed and welcoming atmosphere

Enjoy games, trivia and dinner nights in Windsor.

🍟 July 16–19 – Amherstburg Poutine Feast
11:00 AM | Amherstburg
Get ready for four delicious days of food and fun at the Amherstburg Poutine Feast. This family-friendly festival brings together a variety of creative poutine vendors serving everything from classic favourites to unique specialty creations.

🎲 July 16 – Brews & Board Games at Walkerville Brewery
5:00 PM | Walkerville Brewery
Gather your friends for an evening of craft beer, delicious bites, and tabletop fun at Brews & Board Games.

🌅 July 16 – Dinner & Sunset Cruise
6:00 PM | St. Clair College Centre for the Arts
Treat yourself to a memorable summer evening with the Dinner & Sunset Cruise. Begin the experience on the rooftop Viewpoint Terrace at the St. Clair College Centre for the Arts, where you'll enjoy a delicious three-course plated dinner while taking in panoramic views of the Detroit skyline and Windsor waterfront.

🍽️ July 17 – Terrace Dinners at St. Clair College Centre for the Arts
| St. Clair College Centre for the Arts
Enjoy an elegant evening of fine dining at the Terrace Dinners series, featuring a four-course meal served on the rooftop terrace overlooking the Detroit skyline and Windsor waterfront.

🌌 July 18 – Dark Sky Nights at Point Pelee National Park
| Point Pelee National Park
Experience the beauty of the night sky during Dark Sky Nights at Point Pelee National Park. Stay after sunset to enjoy one of Ontario’s premier stargazing destinations.

🤠 July 18 – Diamonds & Denim Country Hoedown Cruise
7:00 PM – 11:00 PM | Windsor Premier Cruises
Put on your cowboy boots and denim for an unforgettable evening aboard the Diamonds & Denim Country Hoedown Cruise.

🎲 July 20 – Card Board Game Night
5:00 PM – 10:00 PM | The Shadowbox Theatre
Gather your friends or come solo for an evening of fun at Card Board Game Night, held on the third Monday of every month at The Shadowbox Theatre.

⚽ July 15 – Canada Celebrates FIFA World Cup 2026™
12:00 PM | City Hall Square
Celebrate the FIFA World Cup 2026™ with a free day of soccer, live music, cultural performances, food trucks, family activities, and fan experiences. Watch the semifinal match on the big screen, enjoy interactive soccer activations, and soak up the festival atmosphere in downtown Windsor. 🌎⚽🎉

🛼 July 17 – Wheels Nights at City Hall Square
6:00 PM – 10:00 PM | City Hall Square
Roll into a nostalgic summer evening at Wheels Nights, a free outdoor roller-skating event inspired by Windsor’s iconic Wheels! roller rink. As part of the Staycation Activation series, City Hall Square transforms into a lively roller rink complete with music, DJs, themed entertainment, colourful lighting, costumes, and roller skate rentals

⛳ July 21–23 – Play for FREE! Roseland Par 3
12:00 PM – 7:00 PM Daily | Roseland Golf Course
Take advantage of Staycation Activation with free access to the Roseland Par 3 Golf Course from July 21 to July 23. Whether you're a beginner learning the game or an experienced golfer looking for a casual round, this family-friendly opportunity makes it easy to enjoy the outdoors while sharpening your skills.

That’s your Windsor-Essex week at a glance.

Whether you’re catching live music under the summer sky, exploring local markets, enjoying a night of comedy, or discovering a new festival experience, there are plenty of ways to make the most of the week ahead.

Get out, explore the community, support local events, and enjoy everything Windsor-Essex has to offer.

— Windsor Pulse