The long weekend is here! We’ve put together a list of fun activities in and around Windsor, Ontario, for you to fill up your days and make some memories with.

Here are 6 things to do Labour Day weekend 2021 in and around Windsor.



We’re big fans of the Windsor International Film Fest and absolutely love their summer programming. The film fest has been hosting their “WIFF Under the Stars”, which transformed Windsor’s waterfront Festival Plaza into a ‘drive-in style’ theatre.

It’s quite an experience to be watching a film with the iconic Detroit skyline right beside you.

Here’s the schedule for the weekend:

  • Friday, September 3
    • The showcase begins at 7:45pm and will offer up the films Titanic followed by Jaws.
  • Saturday, September 4
    • At 10am, The Aristocats will be playing for families to enjoy.
    • Mrs. Doubtfire begins showing at 1pm
    • At 7:45pm, it’ll be a secret cinema double feature! Clues will be revealed on WIFF’s social media channels as the date approaches.
  • Sunday, September 5
    • Another 10am family feature will offer up Moana on the big screen
    • Sunday evening is a night of crime as Goodfellas, followed by the Wolf of Wall Street, begins at 7:45pm.


Before heading to the movies, head out for a meal at the outdoor food hall. You can even order takeout from the food hall and bring it with you to enjoy while at WIFF Under the Stars.

Presented by St. Clair College and the Alumni Association, the Outdoor Food Hall turns Lanspeary Park’s outdoor rink into the city’s largest patio. It features multiple restaurants and chefs all on a single menu and it’s licensed to serve beer and wine, too! Since the rink has a massive canopy overtop, it also protects guests from the summer sun and any rain, offering an all-weather patio.

It’s operating Friday 5-9, Saturday 3-9 and Sunday 3-8. This weekend will showcase Tropical Hut Philippine Cuisine and Smokies BBQ.

To be as safe as possible, the Outdoor Food Hall is a digital, contactless, cashless experience that’s super easy and convenient to eat and drink at.


Why not slow things down by finding a great spot to watch nature, skylines or people? Grab some takeout from the Outdoor Food Hall or any of your favourite restaurants, lay a blanket down and enjoy a good ol’ fashioned picnic. We’ve put together some great suggestions for spots you might enjoy.


Looking to plan a great day in the city? Start it off at 10am on Saturday, September 4, by heading out on Windsor’s most Instagrammable tour.

Zip around Windsor on an official Bird Canada electric scooter, rolling through streets and alleys to see the many visually stunning ways artists, both local and internationally renowned, have used the urban landscape as their canvas.

The Windsor Graffiti Scooter Tour will take you to some of Windsor’s best photo spots and ensure you get the perfect pic. It’s a great way to explore the city for both tourists and locals alike and you’ll be able to leave with great shots that will give all your friends FOMO.

Our local (and extremely knowledgeable) guide will take you on a 12 kilometre route to see well over 20 murals and takes you through one of the city’s most fabled alleys, highlights a side of Windsor many may have never seen before.


Wanting a more rural experience? The Wine Trail Ride cycling tour brings riders around Canada’s southernmost wine region, tasting at least 12 different wines while feasting on a progressive meal at the stops along the way.

With the weather looking absolutely gorgeous this weekend, it’s a perfect way to enjoy some outside time, the company of friends and, of course, some pretty amazing wine and food.

The Wine Trail Ride cycling tours take place each and every Saturday and Sunday at 10:30am.


Apple picking season is officially upon us and makes for a great family activity. We’ve put together an ultimate guide to help you pick-your-own apples across the Windsor-Essex region.

From the best spots to head out to on your apple picking adventure to some helpful tips to know before you head out and for when you’re on the farm, we’ve got you covered.

Not all locations are open this weekend, so be sure to confirm their hours of operation with them.