Windsor, Labour Day may be behind us but the calendar isn't slowing down.
This week (Sep 3–10) the 172nd Harrow Fair wraps up, the Windsor Food Festival rolls through the riverfront, a 400-drone show lights up Dieppe Gardens, and Nelly headlines The Colosseum at Caesars. Add an Eagles tribute, a punk-rock opera, and stand-up from DJ Demers, and there's no shortage of ways to close out summer.
Here's your full guide to the best of Windsor-Essex this week.

🎬 September 5 – Dirty Dancing: Dinner & a Movie
6:00 PM Doors • 6:30 PM Dinner • 8:00 PM Movie | Chrysler Theatre, 201 Riverside Dr W, Windsor

Enjoy a special evening featuring a 3-course plated dinner in the Skyline Ballroom before heading to the Chrysler Theatre to watch the classic film Dirty Dancing. Dinner seating is reserved, while the movie is general admission. 🍽️🎞️💃

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🍽️ September 4, 5 & 6 – Windsor Food Festival 4.0
Sep 4–6 • 4:00 PM – 12:00 AM | Riverside Festival Plaza, Windsor

Experience one of Windsor's biggest celebrations of food, culture, and entertainment! Enjoy a weekend filled with delicious food vendors, food trucks, live performances, cultural experiences, and family-friendly fun along the waterfront. 🌮🎶🎉

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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.

🎸 September 4 – 89X Birthday Bash
7:30 PM | The Colosseum at Caesars Windsor
Get ready for a night of alternative rock as the 89X Birthday Bash returns to Windsor! The lineup features Default, The Blue Stones, and Fionn, with Canadian rockers Default celebrating the 25th anniversary of their album The Fallout.

🎶 September 5 – Leamington’s Music Onthe42 Summer Concert Series: The S’Aints
8:00 PM | SUNSET® Amphitheatre, Seacliff Park
Enjoy a free Labour Day weekend concert as The S’Aints take the stage at Leamington’s SUNSET® Amphitheatre

🎶 September 5 – Majhaestic Night with Prem Dhillon
9:00 PM | Chrysler Theatre
Enjoy an evening of Punjabi music as Prem Dhillon takes the stage at the Chrysler Theatre for a live concert. The event offers fans an opportunity to experience Punjabi music and live performance in the intimate setting of the St. Clair College Centre for the Arts.

🎸September 6 – Stone & Sky Pelee Island: Nil-A-Nova Big Band
6:00 PM – 7:00 PM | The Quarry on Pelee Island
Enjoy an evening of live big band music as the Nil-A-Nova Big Band takes the stage as part of the Stone & Sky Music & Art Series on Pelee Island.

☀️ September 6 – Summer Sundays with Cherry Rock Lounge & 89X
7:30 PM – 10:00 PM | Cherry Rock Lounge
Keep the weekend going with Summer Sundays, a lively evening featuring live music, great vibes, and a fun Sunday atmosphere in partnership with 89X.

🎤 September 8 – Take It To The Limit: The Music and Legacy of the Eagles
7:00 PM – 9:00 PM | Capitol Theatre Windsor
Eagles fans can enjoy an evening of live music with the acclaimed “Take It To The Limit” Eagles tribute.

🎤 September 10 – Nelly Returns to The Colosseum Stage
8:00 PM | The Colosseum at Caesars Windsor
GRAMMY Award-winning and multi-platinum rapper Nelly returns to The Colosseum stage for an evening of hip-hop and crossover hits.

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

😂 September 4 – Friday Comedy Session LIVE at Tipsy Toucan
8:00 PM – 9:30 PM | The Tipsy Toucan
Windsor Laughs kicks off the weekend with a rotating lineup of comedy club regulars and special guests from Windsor, Detroit, and beyond.

😂 September 5 – DJ Demers LIVE Comedy at Tipsy Toucan
8:00 PM – 9:30 PM | The Tipsy Toucan
Windsor Laughs presents D.J. Demers, a nationally recognized comedian known for appearances on The Tonight Show with Jimmy Fallon, America’s Got Talent, and Conan.

😂 September 8 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Phog Lounge
Every week, Phogheads transforms Phog Lounge into one of Windsor’s most fun and intimate comedy rooms, showcasing local and touring stand-up talent.

🌾 September 3–6 – The Harrow Fair
See event details | Harrow Fairgrounds
Celebrate the 172nd Harrow Fair, one of Ontario’s longest-running agricultural traditions, dating back to 1854. This Labour Day weekend celebration brings together the community with livestock and 4-H shows, agricultural and homecraft exhibits, midway rides, family activities, live entertainment, and the annual parade

🍽️ September 4–6 – Windsor Food Festival
See event details | Riverfront Festival Plaza
Treat yourself to a weekend of global flavours, live entertainment, music, cultural performances, and community funat the Windsor Food Festival. Explore a diverse selection of local and international food vendors while enjoying live music, DJs, dance performances, and family-friendly activities along Windsor’s waterfront.

🎆 September 5 – Tecumseh End of Summer Celebration
6:30 PM – 10:30 PM | Lakewood Park
Celebrate the end of summer at the Tecumseh End of Summer Celebration, featuring a community bonfire, marshmallow roast, live beachside music, and a spectacular fireworks display. Gather with family and friends, enjoy roasting marshmallows and making s’mores, and relax by the water while a local artist provides live musical entertainment.

🇨🇦 September 6 – Great Canadian Riverfront (DRONE SHOW)
4:00 PM – 9:30 PM | Dieppe Gardens
Celebrate Canada with a free red-and-white waterfront celebration featuring live music, food trucks, lawn games, family activities, and Canadian-themed fun. Performances include Buck Twenty at 4:00 PM, Ultrasonik at 6:00 PM, and The S’Aints at 8:00 PM, leading into a spectacular 400-drone show over the Detroit River.

Enjoy markets, shows, fashion at Windsor.

🍬 September 3 – Make a Candy Corn Gnome Jar!
4:30 PM | Windsor Public Library – Central Branch
Get creative this autumn with a fun Candy Corn Gnome Jar craft at the library! Participants can make a cute and functional gnome-themed jar, perfect for storing seasonal treats and adding a festive touch to their home

🎭 September 3–5 – Lizzie
See event details | Masonic Temple Ballroom
End the summer with Lizzie, a punk-rock opera inspired by the infamous story of Lizzie Borden. Combining powerful music, dramatic storytelling, and a bold theatrical style, this unique production offers an unforgettable night of live theatre.

🧘 September 3 – Free Introductory Tai Chi Class
See event details | Fung Loy Kok Institute of Taoism
Discover the gentle practice of Taoist Tai Chi® at this free open house. Learn about the traditional 108-movement set, try beginner-friendly movements, and explore how Tai Chi can support balance, focus, and overall well-being.

🐕 September 3–6 – Labour Day Weekend Dog Show
9:00 AM – approximately 4:00 PM | Colasanti’s Tropical Gardens
Enjoy the Labour Day Weekend Dog Show at Colasanti’s Tropical Gardens in Kingsville.

🍦 September 4–6 – Amherstburg Open Air Weekends: Open Air Finale
3:00 PM Friday – 8:00 PM Sunday | Downtown Amherstburg
Soak up the final summer weekend of Amherstburg Open Air! Enjoy pedestrian-friendly downtown streets, local shops, restaurants, sweet treats, refreshing drinks, vendor markets, live entertainment, and family-friendly activities.

🌙 September 4 – Amherstburg Open Air Night Markets
See event details | Downtown Amherstburg
Enjoy a unique night market atmosphere featuring live entertainment, great food, local vendors, and handmade treasures.

🥕 September 5 – Downtown Windsor Farmers’ Market
See event details | Downtown Windsor, Pelissier & Maiden Lane
Discover farm-fresh fruits, vegetables, produce, and unique artisan food products at the Downtown Windsor Farmers’ Market.

🛍️ September 5 – Lakeside Market
8:00 AM – 1:00 PM | Atlas Tube Centre
Presented by Lakeside Home Solutions, the Lakeside Market brings together local farmers, growers, makers, artisans, small businesses, food vendors, and community organizations for a vibrant community market.

🐕 September 4–5 – CKC Canine Good Neighbour Testing
10:00 AM – 3:00 PM | Colasanti’s Tropical Gardens
Give your dog the opportunity to take part in Canine Good Neighbour certification testing at Colasanti’s in Kingsville.

🎨 September 5 – Art Windsor-Essex Guided Tour
2:00 PM – 3:00 PM | Art Windsor-Essex
Discover the stories and ideas behind the artworks at Art Windsor-Essex with the gallery’s friendly Gallery Guides.

🚶 September 5 – Kidney Walk – Kingsville
4:00 PM – 9:00 PM | Lakeside Park
Join friends, families, and community supporters for the Kidney Walk – Kingsville, a family-friendly community event raising awareness and funds for kidney research and education.

🏇 September 6 – Leamington Raceway Horse Races
1:00 PM | Leamington Raceway
Head out to Leamington Raceway for an exciting day of live horse racing and entertainment.

🍎 September 10 – Thiessen Orchards Opening Day
See event details | Thiessen Apple Orchards
Get ready for the return of autumn vibes and family fun as Thiessen Orchards opens for the season!

Enjoy games, trivia and dinner nights in Windsor.

🛥️ September 5 – Yacht Rock Dance Party at Walkerville Brewery
8:00 PM | Walkerville Brewery
All aboard! Celebrate Labour Day Weekend in style at the Yacht Rock Dance Party. Break out the captain’s hats, boat shoes, and retro shades for a fun night of yacht rock, dancing, and throwback vibes.

🚗 September 4–6 – Disney Cars & Super Trooper 3 Drive-In Movie Night
See event details | The Boonies Drive-In Theatre
Get ready for a fun drive-in movie weekend at The Boonies! Disney’s Cars returns to the big screen to celebrate its 20th anniversary, bringing Lightning McQueen and his friends back for a nostalgic family movie experience. The weekend also features Super Trooper 3, giving moviegoers a double-feature-style lineup under the stars.

🖤 September 5–6 – Asylum Windsor’s Monthly Dark Alternative Night
See event details | Downtown Windsor
Step into Windsor’s dark alternative and goth music scene at Asylum’s monthly night out. Enjoy an evening of DJs, dancing, and alternative music in a welcoming downtown atmosphere.

🎲 September 9 – Game Nights @ Central Library for KIDS!
6:00 PM – 8:00 PM | Windsor Public Library – Central Branch
Enjoy a fun and free drop-in game night for kids and families at the Central Library! Play a variety of board and card games in a relaxed, welcoming environment.

🧠 September 3 & 10 – Trivia Night at The Manchester Bar
7:00 PM – 9:00 PM | The Manchester Bar
Put your knowledge to the test at Trivia Night at The Manchester Bar! This weekly trivia night welcomes teams and drop-ins for a fun, casual evening of questions, friendly competition, and entertainment in downtown Windsor

That's your week across Windsor-Essex. Whether you're catching Nelly at Caesars, watching drones light up the river, or just grabbing a plate at the Harrow Fair, there's plenty to keep you busy before the leaves start turning. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse