As May winds down and the city begins to buzz with the promise of summer, The DRIVE invites you to dive into the rhythm of the season.
Whether you’re chasing golden hour vibes or late-night grooves, we’ve lined up a thoughtfully curated list of live music events to soundtrack your end-of-month plans. From cozy corners to open-air stages, there’s no shortage of places to soak up the sound.
So mark your calendars, grab your crew, and let the music lead the way!
Turn It Up at Windsor Ribfest
Nothing says summer kickoff like smoky BBQ and loud guitars. Wicked Truth is hitting the stage at Windsor Ribfest to bring the heat with a high-energy rock set that’s as bold as the sauce.
With the riverfront as your backdrop and ribs in hand, this is a Thursday night built for good food, good music, and zero regrets.
Where: Riverfront Festival Plaza – 370 Riverside Dr E, Windsor
When: Thursday, May 23rd from 7:30pm-10:30pm
Wine, Vibes, and Velvet Vocals at Daisy & Co.
Live music and a glass of wine – what more could you ask for to close out the month of May? Daisy & Co. Wine Bar is turning up the charm with two intimate evenings of sound and sip.
With cozy ambiance, curated performances, and your favorite pour in hand, these nights are made for unwinding in style!
Where: Daisy & Co. Wine Bar – 41 King Street West, Harrow
When & Who:
- Friday, May 23rd @ 6:30pm – Joe Mouawad & Karaoke
- Friday, May 30th @ 6:30pm – Phil Charrette
The Lion's Head Presents...
The Rose City Rockers are back and ready to shake the walls of the legendary Lions Head stage with not one, not two, but three killer sets of ’70s blues rock and tracks off their brand-new album, BluesRock REvolution. This is the kind of night that reminds you why live music matters.
Tables fill fast! Get there early, grab a drink, and settle in for a proper Friday night throw-down.
Where: Lion’s Head Tavern – 7880 Wyandotte St E, Windsor
When: Saturday, May 24th @ 8:30pm
Bittersweet Sounds, No Frills Needed
Bitters & Lost Charm are bringing their signature blend of grit and glow to the Meteor stage where the lights stay low, and the music speaks loudest.
Step into a night of raw emotion and magnetic sound. No gimmicks – just good music, dim lights, and a crowd that gets it.
Where: Meteor – 138 University Ave W, Windsor
When: Saturday, May 25th @ 8:00pm
