From races to picnics, plenty of summer events in Windsor-Essex. Here’s a look at what’s happening from July 23-26, 2026. Run with Responders Sunday July 26 Organizers of the 2026 Run With Responders 5K are inviting resident runners to join them on a five-kilometre (5K) route along the Windsor Riverfront Trail on Sunday, July 26, 2026. Nearly 450 individual runners and walkers of all ages are expected to take part in this unique first responder–themed charity run celebrating all frontline service providers. Windsor Fire and Rescue Services Chief James Waffle, Windsor Police Service Chief Jason Crowley, and Essex-Windsor Emergency Medical Services (EMS) Chief Justin Lammers challenge local first responders and residents to register and join the 4th Annual Run With Responders 5K, Kids Dash and AM 800m Run to support local charities. This charity 5K will be a rain-or-shine event. Race-day registration begins at 7:30 a.m. with the run to start at 9:00 a.m. sharp. All runners in the 5K will receive a high-quality event t-shirt and finisher’s medal. Fringe Windsor Independent Theatre Festival Thursday July 23 to Sunday July 26 Fringe Windsor is a four-day long performing arts festival that provides a platform for artists to self-produce live shows. Kingsville Pro Rodeo Thursday July 23 to Sunday July 26 Join us for four days of rodeo action, live entertainment, and family-friendly fun at the Kingsville Pro Rodeo! Summer Theatre – Talley’s Folly Thursday July 23 to Sunday July 26 Heritage Colchester is pleased to host the Inspired Acting Lab’s presentation of Talley’s Folly, a 1980 play by American playwright Lanford Wilson. AWE Summer Nights Thursday July 23 5:00 pm to 9:00 pm There’s something new happening this summer. AWE Summer Nights, every Thursday in July & August! Bring Your Own Vinyl Night Thursday July 23 6:00 pm to 8:00 pm BYO-Vinyl. We’ll pour the beer. At the Walkerville Brewery, we’re teaming up with CJAM on Thursday, July 23rd from 6-8PM for Bring Your Own Vinyl Night, a community-driven experience! Live at the Lighthouse in Kingsville – Acoustics Unlimited Thursday July 23 7:00 pm to 8:30 pm Join us every Thursday throughout July and August for a free evening of live music at the gazebo next to the Lighthouse Bush Take on The Colosseum Stage Thursday July 23 8:00 pm British rock band, Bush, is set to take on The Colosseum stage with special guest JJ Wilde at Caesars Windsor. Amherstburg Open Air Weekends Friday July 24 to Sunday July 26 Amherstburg Open Air Weekends are the perfect weekend adventure with activities for all ages! Lakeshore Ribfest Friday July 24 to Sunday July 26 Bring your appetite and enjoy a weekend of mouthwatering barbecue, family fun, and live entertainment at Lakeshore Ribfest! Amherstburg Open Air Night Markets Friday July 24 Check out Amherstburg Open Air Night Markets every Friday Evening until the end of the summer! Bridgerton Tea At The Park House Museum Friday July 24 11:00 am to 5:00 pm Join us for an afternoon of Bridgerton Tea at the Park House Museum! Uncorked Weekend Friday July 24 to Saturday July 25 Ease into the holiday weekend with an afternoon of smooth jazz, exceptional wine, and authentic wood-fired pizza. Blonde Ambition – The Madonna Tribute Dinner Show Friday July 24 6:00 pm EXPRESS YOURSELF and join us for a spectacular two-night Madonna Tribute Dinner Show. Wheels Nights at City Hall Square Friday July 24 6:00 pm to 10:00 pm Wheels Nights is a Friday evening summer event series taking place at City Hall Square in partnership with the DWBIA. Gilligan’s Island 3 Hour Tour Cruise Friday July 24 6:00 pm to 10:00 pm Come take your chances on this 3 hour Gilligan’s Island themed tour! 90’s Alt Night at Sandwich Brewing Co Friday July 24 6:00 pm It’s 90’s alt night at the Sandwich Brewing Co! Enjoy live music in the Biergarten with Chris Mazar. Tecumseh Twilight Friday July 24 6:30 pm to 10:30 pm Food trucks, cool cars, and a movie under the stars… sounds like the perfect night to us! Scarehouse Summer Scream Friday July 24 7:00 pm to 10:00 pm For one night only, Scarehouse is reopening its doors… for the 3rd Annual Summer Scream. Arts at the Marina Saturday July 25 to Sunday July 26 This two-day event held at the scenic lakeside Leamington Municipal Marina/Rick Atkin Park, features dozens of artisans on display, live local music, food and refreshments. Erie Street GastroPub Block Party Saturday July 25 to Sunday July 26 5 Weekends of Music with Great Food, Patio and Drinks, extended patio and festival. Full details of schedule and entertainers. Leamington’s Music Onthe42 Summer Concert Series – Windsor Symphony Orchestra Saturday July 25 The Municipality of Leamington is excited to announce the full lineup for the 2026 Music Onthe42 Summer Concert Series, returning to the SUNSET® Amphitheatre at Seacliff Park with free live music all summer long! Lakeside Market Saturday July 25 8:00 am to 1:00 pm Don’t miss the Lakeside Market! Downtown Windsor Farmers’ Market Saturday July 25 9:00 am to 2:00 pm Discover fresh local produce, artisan foods, family fun, and community events at the Downtown Windsor Farmers’ Market. Farmer’s Market In The Quarry Saturday July 25 10:00 am to 1:00 pm Join Stone and Sky at the Quarry for their weekly Farmers Market! Maidstone Museum Open Garden Tour Saturday July 25 to Sunday July 26 Come tour over 70 species of native trees, shrubs, and plants in the garden at Maidstone Museum! Forest Festival at The Canadian Transportation Museum and Heritage Village Saturday July 25 10:00 am to 4:00 pm Join Us for Forest Festival! Come on out for an unforgettable day filled with fun! Lots to do for the whole family! Art Series Workshop: Watercolour Painting Saturday July 25 10:00 am to 12:00 pm Learn to paint a stunning floral composition using the fluidity and elegance of watercolor. City Cinema Saturdays Saturday July 25 11:00 am to 2:00 pm Presented in partnership with the Windsor International Film Festival, City Cinema Saturdays invites visitors to enjoy free family-friendly movies and popcorn every Saturday morning throughout the summer. Cars for a Cause x OneDay Dreams Saturday July 25 12:00 pm to 5:00 pm Discover an unforgettable showcase of exotic vehicles, community car culture, and family-friendly experiences at Cars for a Cause x OneDay Dreams. Duff-Bâby House – Open Days Saturday July 25 12:00 pm to 4:00 pm Following extensive restoration work by the Ontario Heritage Trust and the installation of new exhibits the Duff-Bâby House is ready to welcome visitors back Exotic Car Show at Mastronardi Estate Winery Saturday July 25 12:00 pm to 4:00 pm Check out sleek rides and fine wines at Mastronardi Estate Winery - Exotic Car Show The Riverfront Big Picnic Saturday July 25 2:00 pm to 8:00 pm The Riverfront Big Picnic transforms Alexander Park into Windsor’s ultimate summer gathering, inspired by classic neighbourhood picnics, family reunions, and carefree afternoons in the park. Blonde Ambition – The Madonna Tribute Dinner Show Saturday July 25 6:00 pm EXPRESS YOURSELF and join us for a spectacular two-night Madonna Tribute Dinner Show. Movie Trivia With Mack Flash at Walkerville Brewery Saturday July 25 7:00 pm to 9:00 pm From cult classics to modern blockbusters, are you ready to test your film knowledge? 80’s & 90’s Double Wham Jam Cruise Saturday July 25 7:00 pm to 11:00 pm Join us for a totally tubular time on the Macassa Bay! Windsor Symphony Orchestra – Summer Concert Series Saturday July 25 Check out the Windsor Symphony Summer Concert Series! Jeremy Dobski LIVE Comedy At Tipsy Toucan Saturday July 25 7:30 pm to 9:00 pm Jeremy Dobski live at the Tipsy Toucan Willistead Manor Summer House Tours Sunday July 26 Discover timeless elegance and rich history with a guided tour of Willistead Manor, Windsor’s iconic 1906 heritage estate set in beautiful parkland. 2026 World Junior Summer Showcase in Windsor Sunday July 26 to Saturday August 1 The Windsor Spitfires Hockey Club will host the 2026 World Juniors Summer Showcase from July 26 - Aug 1 at the WFCU Centre. Amherstburg’s Gone Car Crazy Show Sunday July 26 10:00 am to 3:00 pm Street Rods, trucks, custom street machines, sport cars and live entertainment. Paws and Pours at Cooper’s Hawk Vineyards Sunday July 26 11:00 am to 5:00 pm Head on out for an afternoon filled with your fur besties and Cooper’s Hawk Wines! Lakewood Mini Market Sunday July 26 11:00 am to 3:00 pm Join us on the Plaza for a vibrant mini market featuring local vendors, handmade goods, delicious treats and so much more! The Plaza is in Lakewood Park South, is free to attend, and is family and pet friendly. Sprucewood Shores Summer Music Series Featuring Fresh Breath Sunday July 26 1:00 pm to 3:00 pm Come see Fresh Breath live at Sprucewood Shores Estate Winery on July 26th! Sunday Sounds At Oxley Estate Winery Sunday July 26 1:00 pm to 5:00 pm Starting May 17th, join us every Sunday all summer long for live music, great food and wine, and good company right here on the estate. Weekends in the Studio! Watercolor Fruits Bookmark with Suela Prendi Sunday July 26 1:00 pm to 4:00 pm Add a pop of colour to your reading time this summer! Culinary Series Workshop: Family Friendly Meals Sunday July 261:00 pm to 5:00 pm Experience how fun and easy cooking can be in this interactive, team-based workshop! Park House Museum Discovery Days Sunday July 26 2:00 pm to 4:00 pm Looking for a fun way to spend your Sundays this summer? Join us for Discovery Days! LaSalle Night Markets Sunday July 26 4:00 pm to 8:00 pm The LaSalle Night Markets are lively and feature talented local artisans and crafters, farm-to-table local produce, delicious food vendors, amazing merchant consultants and local businesses, exhibiting their handmade and handcrafted products. Stone and Sky Music & Art Series At the Quarry – Austin Pietro Ensemble, Cassandra Caverhill, & Tina Newlove Sunday July 26 5:30 pm Come experience all the sights and sounds at the Stone and Sky Music & Art Series! Jazz Night at the Brewery Sunday July 26 6:00 pm to 9:00 pm Join us on the last Sunday of the month from 6-9PM to enjoy some silky-smooth live jazz by The Coffee House Combo! Albanian Boat Cruise Party Sunday July 26 6:00 pm to 10:30 pm Join NV Entertainment this summer for our Albanian Boat Cruise Party located on the Detroit River! All Canadians and Americans are welcome! Neighbourhood Nights – Ford Test Track Sunday July 26 6:30 pm to 9:00 pm Neighbourhood Nights brings the celebration closer to home with FREE community gatherings taking place in parks across all 10 wards of the city.
