What’s Up YQG: Sandwich Summer Series, Rib Fest, Leamington Fair

CTV Windsor's Melanie Kentner and 89X’s Jonny Parks feature the Sandwich Summer Series with Tailgate Takeout and Sandwich Brewing Company.

Summer isn’t quite here yet, but there are several summer-like events happening in Windsor-Essex this weekend.

Here’s a look at Windsor-Essex events from May 21-24, 2026.

Sandwich Summer Series

Vol. 1 of the Sandwich Summer Series drops Sunday, May 24! Join New Rock 89X, Dan MacDonald and Tailgate Takeout on Sunday, May 24th from 11a-3p on the Sandwich Brewing Co. patio for brunch, brews and a live performance from Crissi Cochrane Special brunch menu Live music Free giveaways

178th Leamington Fair

Thursday May 21 to Sunday May 24

The Leamington Fair is back with rides, live shows, midway games, fair food, and classic family fun for everyone!

Perfect Pouring Dinner: Nostalgic Carnival Night

Thursday May 21 7:00 pm

Check out the Perfect Pouring Dinner at Banded Goose!

George Thorogood & The Destroyers

Thursday May 21 7:30 pm

Be there when George Thorogood & The Destroyers hit The Colosseum stage with special guest The Marshall Tucker Band on Thursday, May 21 at 8 PM.

Northern Heat Ribfest

Friday May 22 to Sunday May 24

The Northern Heats Rib and Beer Fest is back for another delicious weekend at Riverfront Festival Plaza!

2026 Speedo Canadian Masters Swimming Championship

Friday May 22 to Sunday May 24

The 2026 Speedo Canadian Masters Swimming Championships takes over the Windsor International Aquatic and Training Centre!

ACT Presents: The Price of Freedom

Friday May 22 7:30 pm to 10:00 pm

Arts Collective Theatre presents The Price of Freedom, a powerful original Canadian play exploring the story of John Anderson

WSO Chorus: Fauré Requiem

Friday May 22 7:30 pm to 9:00 pm

An uplifting evening of choral music offers a moving and reflective experience that brings together timeless sacred works performed with beauty and emotional depth.

Dark Sky Nights – Point Pelee National Park

Saturday May 23

Explore the park after dark and experience the dark skies of Point Pelee National Park.

Essex County in the War of 1812 Re-enactment

Saturday May 23

See history come alive at the War of 1812 period re-enactment with participants from Fort Malden, Provincial Marine Amherstburg, Voyageur, and others.

Erie Street GastroPub Block Party

Saturday May 23 to Sunday May 24

5 Weekends of Music with Great Food, Patio and Drinks, extended patio and festival. Full details of schedule and entertainers.

Downtown Windsor Farmers’ Market

Saturday May 23 9:00 am to 2:00 pm

Discover fresh local produce, artisan foods, family fun, and community events at the Downtown Windsor Farmers’ Market.

Hike 42 – A Wildflower Discovery

Saturday May 23 10:00 am to 1:30 pm

You’ll embark on a guided three-mile hike, complete with wine tasting and a gourmet camp-style lunch crafted from local ingredients by our Culinary team, prepared fireside.

Breweries Cideries & Distilleries

Nostalgic Book Fair

Saturday May 23 12:00 pm to 5:00 pm

Remember that nostalgic book fair feeling? We’re bringing it back … and this time you’ve got adult money! Join us on Saturday, May 23rd from 12-5 PM at Walkerville Brewery for an afternoon filled with all your favorite book fair vibes.

90’s Dance Cruise

Saturday May 23 6:00 pm to 10:00 pm

Get your kicks on the Macassa Bay for our 1st 90’s Cruise of the season!

A Night in Nashville

Saturday May 23 6:00 pm

Get ready, Windsor — we’re bringing the heart of Broadway straight to downtown for one unforgettable night.

MagicBox: An Evening of Wonder

Saturday May 238:00 pm to 10:00 pm

Treat yourself to an unforgettable evening of astounding and awe inspiring close-up magic at The Shadowbox Theatre, featuring four world-class magicians!

Electro on Erie

Saturday May 23 9:00 pm

Electro lounge beats all night long with resident DJ, Greg Gnyp + new DJs every week.

Walkerville Walking Tour

Sunday May 24 10:00 am to 12:00 pm

Join us on a 3-kilometer, one and a half hour walking tour of Walkerville, one of Windsor’s most distinct and beautiful neighborhoods.

Rum Runners Tour – SOLD OUT

Sunday May 24 11:00 am to 3:00 pm

Hop aboard for a 4-hour thrill ride filled with gangsters, rumrunners, comedy, music, and a lively speakeasy lunch show.

The Perfect Pairing – CHV

Sunday May 24 12:00 pm

Experience the art of wine pairing with a deconstructed charcuterie board - fun, interactive, and delicious!

Weekends in the Studio! Neurographic Art with Suela Prendi

Sunday May 24 1:00 pm to 4:00 pm

Join us for a fun, family-friendly drop-in studio activity this weekend at the gallery!

Sunday Sounds At Oxley Estate Winery

Sunday May 241:00 pm to 5:00 pm

Join us every Sunday all summer long for live music, great food and wine, and good company right here on the estate.

Water Sounds

Sunday May 24 2:00 pm to 6:00 pm

Join 4th Wall Music in collaboration with ERCA for our concert, “WATER SOUNDS”. Our latest nature awareness concert exploring the sounds, movement and presence of water.

Windsor City Bus Tour – Where Canada Begins

Sunday May 24 2:00 pm to 4:00 pm

The Windsor City Bus Tour: Where Canada Begins is a two-hour, guided experience that brings the city’s most fascinating stories, landmarks, and viewpoints to life—right from the comfort of your seat.

Saxappeal Presents – Flowers: A Tribute to Prince

Sunday May 24 7:00 pm to 9:30 pm

Windsor, Ontario!! Get ready to groove and celebrate Prince’s iconic hits live and in person for FLOWERS: a Tribute to Prince!