July’s here, and it’s all about good tunes, great company, and glass-in-hand moments.
The DRIVE is here to keep your calendar packed and your playlist loud.
Whether you’re after a laid-back acoustic set or a night of dancing under the stars, there’s a spot (and a soundtrack) waiting for you. Windsor-Essex knows how to do summer right – so mark your calendars, round up your people, and make every night a little louder.
Dine, Sip & Howl at the Moon
Long summer nights, live music, and wine under the stars – Oxley Estate Winery’s Howl at the Moon dinners are back, and the 2025 lineup is one you won’t want to miss.
An evening of great food, local wine, and live music timed perfectly with the full moon and a seasonal tradition worth marking on your calendar.
Where: Oxley Estate Winery – 533 County Rd 50 E, Harrow
When: Thursday, July 10 | Doors open at 8:00pm
Throw It Back at the 90s Dance Party: VOL 4
Dig out your chokers, snapbacks, and platform shoes – Walkerville Brewery is hosting the ultimate 90s throwback party!
DJ xxXero will be spinning the biggest dance hits and iconic anthems from the decade that gave us boy bands, grunge, and TRL. Bonus points for showing up in your best 90s gear.
Where: Walkerville Brewery – 525 Argyle Rd, Windsor
When: Saturday, July 12, 2025 | 8:00 PM – 11:59 PM
Jazz, Wine & Vineyard Vibes
Picture this: a glass of local wine, mellow rhythms in the air, wood-fired pizza in hand, and the summer sun on your face. It’s not just a show – it’s a vibe.
Free to attend, no ticket needed. First-come, first-served seating. Get there early, grab a glass, and claim your spot under the sun.
Where: Pelee Island Winery – 455 Seacliff Dr, Kingsville
When: Sunday, July 14 | 1:00pm to 5:00pm
Summer Sounds with Tim McDonald
Ease into your weekend with an evening of live music, good food, and chill company as Tim McDonald takes the stage at Daisy & Co.
Perfect for patio drinks, bites, and easygoing summer tunes.
Where: Daisy & Co – 41 King Street West Harrow
When: Friday, July 18, 2025 | Doors open at 6:30 PM
Country Hits & Good Times at Caesars
Get ready for a night of unforgettable country anthems as Jake Owen rolls into Windsor with special guest Uncle Kracker on The Driftwood Ramble Tour.
Big hits, good vibes, and a high-energy show you’ll be humming all the way home.
Where: The Colosseum at Caesars Windsor – 377 Riverside Dr E, Windsor
When: Friday, July 25, 2025 | 8:00 PM
