Another summer weekend in Windsor, Ontario, another jam-packed schedule of amazing things to do!

A second weekend in a row with just too many events to list, here are some of the things we think you should get out and do to make an entire weekend of summer fun out of!



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Why not stroll through an art gallery with a view and enjoy cocktails, craft beer, treats, and music while taking in the arts.

On Thursday, August 17, 2023 (and on the third Thursday of each month), from 5pm to 9pm, Art Windsor-Essex hosts AWE at Nights featuring art activities, food and beverage as well as lively entertainment. Being located along the riverfront and a prime location for sunset viewing, you can come on out for the beautiful views – both inside and out!



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The Ouellette Car Cruise builds on the nostalgia of Windsor’s storied automotive history and seeks to engage car enthusiasts, hobbyists and the community at large in celebration of our deep automotive roots.

Cruisers begin gathering on Friday, August 18, at Riverfront Festival Plaza at 1pm in the heart of downtown Windsor. The cavalcade of roaring engines and shining chrome begins at 6pm.

The route takes cruisers on a tour of the city from Ouellette Avenue to Tecumseh Road East and from Riverside Drive to Pillette Road.



Also on Friday, food trucks, classic cars, and a movie under the stars are on the list for Tecumseh Twilight, happening at McAuliffe Park (2391 St. Alphonse St.) from 6:30pm to 10:00pm.

The event begins with a classic car show and bites to eat from food truck vendors that will be onsite. There are other fun activities planned for the kiddos, too, before the movie, The Incredibles, begins at 8:30pm.


Something else is happening on Friday?!?! More like Fri-YAY!

The second Mill St. Market of 2023 will take place along Mill Street West in Leamington. This family-friendly, free outdoor street festival features delicious street food, handcrafted items, craft beer and cocktails, local wine, musicians and artists.

WindsorEats will even be on site serving up our tasty mojitos!

Dropped on Drouillard


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Dropped on Drouillard takes place this Saturday, August 19, and we’ve got all the details you need to know!

The festival can be described as Windsor, Ontario’s only all-day urban street and culture festival in the heart of the Ford City neighbourhood.

Read our Ultimate Guide of the 2023 Dropped on Drouillard to learn everything you need to know about the 2023 edition of the festival.