What’s Up YQG: Summer Sundays at Cherry Rock Lounge, Jann Arden, waterfront midway

CTV Windsor's Melanie Kentner and 89X’s Jonny Parks take us through events and entertainment in the city this weekend.

You can tell we’re on the brink of Summer because there’s non-stop action on the Windsor-Essex events calendar, including a great way to extend the weekend at Cherry Rock Lounge.

Here’s a look at local events June 18-21

Summer Sundays with Cherry Rock Lounge & 89X

Sunday June 21 7:30 pm to 10:00 pm

Celebrate with Cold Drinks, Great Vibes, and LIVE Music! Keep the good times rolling, head to Cherry Rock Lounge and Summer It UP!

Prisoner is making their Windsor debut on the Call Of The Reaper Canadian Tour! Fresh off their sophomore album “Kill The King”, Prisoner is taking the country by storm with thunderous drums, blazing riffs and soaring vocals. Direct support form Edmonton’s Lewd Antics and London’s No Exceptions

Windsor Waterfront Midway

Friday June 12 to Sunday June 28

Step right up! The Windsor Waterfront Midway is back for another year of summer fun!

Jann Arden Live at Caesars Windsor

Friday June 19 8:00 pm

Be there when Jann Arden takes The Colosseum stage on Friday, June 19th!

Carrousel of the Nations – Weekend Two

Friday June 19 to Sunday June 21

Explore cultures from around the world by visiting each country’s village at the award-winning Carrousel of Nations!

Free Family Fishing

Saturday June 20 to Sunday June 21

Fish for free in Windsor Essex!

Opening Of We Were Always Here Exhibition

Saturday June 20

Visit the Exhibit “We Were Always Here”, a celebration of the 2SLGBTQ+ community in history at the Park House Museum.

Resurrection: Recent Works by Gene Lotz

Saturday June 20 to Monday June 29

Join us for Resurrection, an exhibition of recent works by Windsor artist Gene Lotz, curated by Lorraine Steele at Shō Art Studios.

Downtown Windsor Farmers’ Market

Saturday June 20 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 June 20 10:00 am to 1:00 pm

Join Stone and Sky at the Quarry for their weekly Farmers Market!

Colchester Markets

Saturday June 20 10:00 am to 3:00 pm

Celebrate local makers, history, and community at the 6th annual Colchester Markets, a lively vendor event supporting the restoration of Colchester Schoolhouse #2.

Duff-Bâby House – Open Days

Saturday June 20 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

Techno BLOCK PARTY

Saturday June 20 4:00 pm to 11:00 pm

June 20th, Art Alley is going full night club, with DJs, drinks, food trucks and block party vibes.

Kingsville Block Party – Summer Solstice – Cottam

Saturday June 20 5:00 pm to 10:00 pm

Enjoy great food, socialize with fantastic people, shop local vendors and businesses, check out Kingsville’s arts and culture scene and let the kids enjoy some fun activities!

Drag Show – Newcomer’s Pride – Death Becomes Queer

Saturday June 20 5:00 pm to 8:00 pm

Join Families First Funeral Home for a special Pride Month fundraiser in support of the Queer Trans Migrant Advocacy Alliance Windsor Essex (QTMAAWE).

Desi AF Featuring: Sonya Vai

Saturday June 20 6:30 pm to 9:00 pm

NYC’s Sonya Vai brings her sharp comedy to Windsor for one unforgettable night of laughs & chaos.

Movie Trivia With Mack Flash at Walkerville Brewery

Saturday June 20 7:00 pm to 9:00 pm

From cult classics to modern blockbusters, are you ready to test your film knowledge?

UK Pink Floyd – A Tribute to the Floyd

Saturday June 20 7:30 pm

Lose yourself in ‘The Songs from every Album Tour’ in 2026! Featuring songs from every one of Pink Floyd’s 15 studio album legacy.

Electro on Erie

Saturday June 20 9:00 pm

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

Tecumseh Farmers Market

Sunday June 21 9:00 am to 1:00 pm

Discover fresh, locally grown produce, handmade goods, and unique treasures from our talented local vendors.

Sunday Sounds At Oxley Estate Winery

Sunday June 21 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.

Music Bingo Trivia at Walkerville Brewery

Sunday June 21 5:00 pm to 7:00 pm

A night filled with a little bit of bingo, a little bit of trivia and a whole lot of music!