Weekend preview: What’s happening in Windsor-Essex June 27-29

Attendees enjoying the Walkerville Distillery District Night Market at the Walkerville Brewery in Windsor, Ont. (Source: Matt Shaheen)

From art fairs and farmers’ markets to live music and theatre, Windsor-Essex offers a vibrant array of weekend activities for every taste.

Here’s a list of what’s happening from June 27-June 29, 2025, according to Tourism Windsor-Essex Pelee Island. Do you have an event to add? Email us at [e-mail].

Windsor Waterfront Midway

Friday June 13 to Sunday June 29

The World’s Finest Shows Midway returns

Walkerville Distillery District Night Market - CANCELLED

Friday June 27 5:00 pm to 11:00 pm

A community event to bring people together.

Free admission at Parks Canada

Friday June 20 to Tuesday September 2

Free admission only applies to places operated by and for Parks Canada including Point Pelee National Park and Fort Malden National Historic Site

We Were Always Here A Celebration of the 2SLGBTQ+ Community in History

Friday June 20 to Friday August 29

Join the Park House Museum and engage in our temporary exhibition, “We Were Always Here, A Celebration of the 2SLGBTQ+ Community in History”.

Korda Artistic Productions – The Guy Who Didn’t Like Musicals

Thursday June 26 to Saturday June 28

Everything in Hatchetfield seemed normal until people began singing... Then, they began dancing... And now, a musical pandemic is sweeping the entire city.

Double Moose Karaoke with KJ Thiago!

Thursday June 26 8:00 pm

We’re going full moose-mode with a Double Karaoke Weekend at the Moose Lodge

Patio Paint Night: June 27

Friday June 27 7:00 am to 9:00 pm

Don’t miss Patio Paint Night at LAC

Lazee G Ranch Seniors Day (50 years and older only)

Friday June 27 9:30 am to 12:30 pm

Seniors Day at the Ranch!

Amherstburg Open Air Weekends!

Friday June 27 to Sunday June 29

Check out Open Air Weekends in Amherstburg

Amherstburg Night Market

Friday June 27 5:00 pm to 10:00 pm

Join us every Friday this summer for the Amherstburg Night Market - part of Open Air Weekends in downtown Amherstburg

Vendor Circuit

Friday June 27 5:00 pm to 10:00 pm

Sad Baby Vintage and Designs by Sav are hosting a pop up at Circuit in Ford City.

Friday Night Lights Bike Ride

Friday June 27 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!

Lakeshore Summer Parks Concert Series: Millen Park – Dave Gatt Band

Friday June 27 7:00 pm to 8:30 pm

Join Lakeshore for an incredible lineup of musicians and musical acts, coming to a park near you!

Bagpipes in the Burg

Friday June 27 7:00 pm to 8:00 pm

Bagpipes in the Burg returns to Open Air Weekends this summer.

Pretty in Pink Movie Night

Friday June 27 7:00 pm to 9:00 pm

Come check out Pretty in Pink movie night at Chrysler Theatre!

Comedy Date Night At Cured Brewing Co.

Friday June 27 8:00 pm to 9:30 pm

Enjoy a night of stand-up comedy with top comedians from Windsor Comedy Club, featuring great craft beer and big laughs.

Glow Cruise

Friday June 27 11:00 pm

Enjoy a fun cruise by Windsor Premier Cruises!

Free Fishing Week

Saturday June 28 to Sunday July 6

Enjoy a free family fishing week!

Downtown Windsor Farmer’s Market

Saturday June 28 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.

Pilates & Matcha Morning

Saturday June 28 9:00 am to 10:00 am

Join Annie of Wolf & Rebel for a 45-minute Pilates workout, followed by a 20-minute sound bath cool down with Alesha from Naturally Grounded Healing. The matcha bar will be available after for a post-workout treat!

Rotary Circle Grand Opening

Saturday June 28 4:00 pm

Bring your family and join us on Saturday June 28!

Chai Social

Saturday June 28 6:00 pm to 7:00 pm

Come as you are, and leave a little more connected.

Windsor Regency Ball

Saturday June 28 to Sunday June 29

Step into a world of elegance and enchantment at the Windsor Regency Ball.

June Besties Cake Decorating Workshop

Saturday June 28 6:00 pm to 8:00 pm

Join us for a sweet night of laughter, icing, and cake at our Bestie Cake Decorating Workshop!

DJ VODKA SODA

Saturday June 28 7:00 pm to 11:00 pm

We’re shaking things up at Banded Goose with something a little different—our first DJ pop-up

Living In Transanity: Drag Show and Summer Party

Saturday June 28 7:30 pm to 10:30 pm

The House of Cures has something special planned for this Pride Month.

Hawaii Five-O Cruise

Saturday June 28 8:00 pm to 11:00 pm

Enjoy a fun cruise by Windsor Premier Cruises!

Rose City Roast Battle – Windsor Comedy Show

Saturday June 28 8:00 pm to 10:30 pm

It’s Canada Day weekend — and we’re kicking it off with a comedy war for the ages.

Brewing For Comedy On Tour – Amherstburg – The Fort

Saturday June 288:30 pm to 10:00 pm

Get ready for a night of top-tier stand-up comedy as Brewing for Comedy takes over Amherstburg.

Disco Cowgirl

Saturday June 28 to Sunday June 29

A glitter-soaked rodeo where retro meets rhinestone!

Sunday Sounds – Oxley Estate Winery

Sunday June 29

Sunday Sounds is back this May at Oxley!

Pints and Poses – Yoga Classes at the Brewery

Sunday June 29 10:00 am

Stretch and sip! Check out yoga classes at the brewery!

A Class & A Glass at Vin Winery

Sunday June 29 10:30 am to 10:30 pm

Join us for a refreshing Mat Pilates class set against the serene backdrop of Vin Winery.

Canada Day Weekend at Vivace Estate Winery

Sunday June 2912:00 pm to 5:00 pm

Join Vivace Estate Winery this Canada Day weekend for a celebration of all things Canadian! From the food to the wine and everything in between!

Lakewood Summer Sounds

Sunday June 29 1:00 pm to 3:00 pm

Enjoy a lively and engaging experience

Size Show 12×12 Art Exhibit

Sunday June 29 1:00 pm to 4:00 pm

The Arts Society of Kingsville hosts the 12x12 art exhibit, a free event inside the Carnegie Arts & Visitor Centre.

Board Game Sunday

Sunday June 29 2:00 pm to 5:00 pm

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

Slow Jam Sunday

Sunday June 29 2:00 pm

Picture this: classic R&B throwbacks, Windsor’s biggest patio, and you, day drinking and dancing with friends. Our DJs will be spinning the smoothest beats all afternoon, setting the perfect scene for an epic Sunday Funday.

Lasalle Night Markets

Sunday June 29 4:00 pm to 8:00 pm

The LaSalle Night Markets feature live music, vendors, and delicious food!

Jazz Night at Walkerville Brewery

Sunday June 29 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!