What’s Up YQG: Grape Fest, Fright Night and more Windsor-Essex events Sept. 12-14

CTV Windsor's Melanie Kentner and 93.9 Virgin Radio's Jonny Parks take us through events and entertainment in the city this weekend.

Celebrate Caboto Club’s 100th Grape Festival, kick off spooky season at AM800’s Fright Night, rock out with Honeymoon Suite, and celebrate runners (or just enjoy the afterparty!) at the Windsor Waterfront Half Marathon - it’s a packed weekend in YQG!

Here’s a rundown of Windsor-Essex events Sept. 12-14:

Caboto Club Grape Fest

Friday September 12 to Sunday September 14

Celebrate Caboto Club’s 100th anniversary at the legendary Grape Festival! Enjoy Italian culture, live music, great food, and family fun.

Entertainment: Friday (19+): Slim Pickerle Duo & Higgi Country Band Saturday (19+): Crisis Club. Sunday (all ages): Portofino Band

Nightly Contests: Grape Stomping & Spaghetti Eating

Food & Drink:Caboto’s famous wood oven pizza & kitchen favourites, Italian desserts and regional Italian wines.

Family Day: Lots of activities and Spaghetti & Grape Stomping contests for the kids, Sailor Sue, Jangles, midway games and more.

AM800’s Fright Night

Friday, September 12, 7pm - 10pm

Kick off spooky season with AM800 and ScareHouse Windsor. It’s a free night of haunted houses. All you have to do is register, show up and try not to scream with fear! Some of the radio and tv team will be dressed up and spooking you throughout the night. Bring a non-perishable or cash donation in support of the Society of St. Vincent de Paul.

Korda Artistic Productions – The Importance of Being Earnest

Friday September 12 to Sunday September 14

In 1890s London, two friends use the same pseudonym for their on-the-sly activities, and hilarity ensues in this brilliant play.

Next to Normal- A Musical Production

Friday September 12 to Sunday September 14

Join Cardinal Music Productions for their powerful rendition of Next to Normal

Accessibility Fest-for-All

Friday September 12 10:00 am to 2:00 pm

The Essex County Accessibility Advisory Committee (ECAAC) is proud to present the second annual Outdoor Accessibility Fest-for-All on Friday

Mill St. Market – 1980’s Glow Party

Friday September 12 5:00 pm to 10:00 pm

The Mill St. Market is specially curated to serve delectable street food and drinks while you shop for handcrafted arts and and crafts lining the modern, reinvented, Mill Street in Leamington.

Back to School Stroll the Streets

Friday September 12 6:00 pm to 8:30 pm

Stroll the Street celebrates Back to School

Friday Night Lights Bike Ride

Friday September 12 6:30 pm

Enjoy the sight of colourfully lit cyclists roll through the streets, bells clacking, as they partake in a pub crawl on two wheels!

Enbridge Presents: Live at The Square with Coffeehouse Combo

Friday September 12 7:00 pm to 9:00 pm

Every Friday evening from July through October 2025, Windsor’s new City Hall Square plaza will transform into a hub of music, culture, and community with Live at The Square.

Brewing for Comedy Festival Kicks Off with Headliner Zach Martina

Friday September 12 7:30 pm to 9:00 pm

Brewing for Comedy Festival Kicks Off with Headliner Zach Martina headlining a FREE SHOW!

Durty little secrets @Cherry Rock Lounge Windsor

Friday September 12 to Saturday September 13

Durty little secrets returns!

Frozen in Time

Saturday September 13

Kids Corner Productions presents Frozen in Time on Saturday, September 13, 2025, with performances at 11:00 AM and 2:00 PM!

Scarehouse Windsor Immersive Dinner Experience

Saturday September 13

Enjoy a 90 minute VIP private themed immersive dining experience.

W.E. Heart Local Presents: Open Farms Day

Saturday September 13

Open Farms is back!

Downtown Windsor Farmer’s Market

Saturday September 13 9:00 am to 2:00 pm

At the Downtown Windsor Farmers’ Market you’ll find farm fresh fruit, vegetables, produce and unique artisan food products from the best our area has to offer.

Children’s Fest

Saturday September 13 to Sunday September 14

Get ready, Windsor-Essex! The 30th Annual Children’s Fest is back and bigger than ever!

Festival of Hawks

Saturday September 13 10:00 am to 3:00 pm

The Festival of Hawks returns to Holiday Beach Conservation Area.

Pop-Up | Permanent Perfection Jewellery

Saturday September 13 10:00 am to 2:00 pm

Permanent Perfection Jewellery is a business that creates bracelets, necklaces, anklets and rings that are welded together

The Future is Female Market

Saturday September 13 10:00 am to 4:00 pm

Come out and support over 30+ local female artisans at The Future is Female Market!

Windsor Fitness Expo 2025

Saturday September 13 11:00 am to 6:00 pm

Get ready for Windsor-Essex’s biggest fitness event of the year!

Electric Avenue Alley Party

Saturday September 13 2:00 pm to 11:00 pm

WindsorEats is bringing back Electric Avenue Alley Party for 2025, a big neighbourhood party that’s pet and family friendly.

Paint Party at Colchester Ridge Estate Winery

Saturday September 13 2:00 pm to 4:00 pm

Join us for a relaxing and creative afternoon at Colchester Ridge Estate Winery!

Windsor Punk Rock Flea Market

Saturday September 13 4:00 pm to 9:00 pm

We’re back! Bigger, better, and more radical. The Windsor Punk Rock Flea Market returns this September 13th to Riverside Banquet Hall

Kitchener Rangers V.S. Windsor Spitfires

Saturday September 13 7:00 pm to 9:30 pm

Come out and support the Windsor Spitfires as they take on the Kitchener Rangers in preseason action to gear up for the OHL regular season!

Lancers Home Opener

Saturday September 13 7:00 pm to 10:00 pm

The Lancers take on the McMaster Marauders!

We Walk The Line – Tribute to Johnny Cash

Saturday September 137:30 pm to 10:00 pm

We Walk The Line is a true Johnny Cash Experience that celebrates the music and lives of ‘The Man In Black’ and his fun loving wife, June Carter.

Honeymoon Suite

Saturday September 13 8:00 pm

Get ready for a night of pure rock nostalgia and high-energy hits as Honeymoon Suite takes the stage at the Chrysler Theatre!

Yungblud with Special Guest Sawyer Hill

Saturday September 13 8:00 pm to 11:00 pm

Yungblud is fast becoming one of the key musical voices of his generation, blending influences from Rock, Punk and Pop to monumental effect.

What Seas, What Shores Celebrate 20 Years of Sonic Exploration

Saturday September 13 9:00 pm to 11:30 pm

What Seas, What Shores Celebrate 20 Years of Sonic Exploration with Special Anniversary Performance Marking Two Decades Since Formation and Ten Years Since Their Landmark Album Spiritual Nap Machine

SOLD OUT! Windsor Waterfront Half Marathon

Sunday September 14

The flattest, fastest, most scenic & spectator friendly course. The Windsor waterfront half marathon & 5km is here to put Windsor on the map for big city races!

Waterfront Half Marathon After Party

Sunday, September 14 When: 12-6 PM

Join us at Walkerville Brewery, the official home of the Windsor Waterfront Half Marathon After Party, and keep the good vibes going. Whether you ran, walked, cheered, or volunteered, this celebration is for you.

We’re taking the party outside with an extended patio, live DJ, and delicious food ready to refuel your post-race hunger. Raise a glass with fellow runners, share your race stories, and bask in the glory of your accomplishment, or just enjoy the party.

Terry Fox Run

Sunday September 14 8:00 am to 12:00 pm

Join us on Sunday, September 14 for the 45th Annual Terry Fox Run at Green Acres Optimist Park in Tecumseh.

Cars for a Cause – Season Closer

Sunday September 14 9:00 am to 5:00 pm

Cars for a Cause is wrapping up their biggest year yet with our first-ever Season Closer, held in partnership with the Windsor Waterfront Half Marathon.

Pints & Poses

Sunday September 14 10:00 am

Stretch and sip! Check out yoga classes at the brewery! $20 for an hour of yoga and a pint of beer!

Farmer’s Markets

Amherstburg Farmers Market

Sunday September 14 12:00 pm to 4:30 pm

The Amherstburg Farmers Market is a welcoming, outdoor space offering a deliberate and diverse, hand-selected lineup of farmers, makers and creators.

Board Game Sunday

Sunday September 14 2:00 pm to 5:00 pm

Sundays are the ultimate fundays at North 42 Degrees Estate Winery!

Flint Firebirds V.S. Windsor Spitfires

Sunday September 14 2:00 pm to 4:30 pm

Come out and support your Windsor Spitfires as they continue their preseason against the Firebirds!

Esteriore Brothers

Sunday September 14 5:00 pm to 8:00 pm

Enjoy Italian pop with the Esteriore Brothers!

Brewing for Comedy Festival

Sunday September 14 7:00 pm to 9:00 pm

This comedy showcase will feature festival standouts, surprise guests, and some of the sharpest up-and-coming voices in stand-up today.