There is so much to do in and around Windsor, Ontario this weekend!

While there are just too many 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!

Caribbean Night Party

WindsorEats’ very first Caribbean Night Party was such a huge success we’ve been bombarded with requests to do it again! So here we go!

Get ready to sway your hips and feel the rhythm at WindsorEats’ Caribbean Night Party on Friday, August 11, 2023!
Leave your worries behind as you step into a tropical paradise filled with infectious beats and sun-soaked vibes. You’ll be mesmerized by a live performance of a steel drum band from Detroit and the enticing aroma of mouth-watering Caribbean cuisine from Stelly’s. You can also dig into some good ol’ American soul food from Mr. Spoon if jerk chicken and patties aren’t your thing.

Whether you’re sipping on some rum punch, trying your hand at soca dancing, or simply lounging, this night promises an fun escape. Grab your colorful attire and join us for a night of carefree revelry.

Friday Night Lights Pub Crawl

Friday Night Lights is a colourful, nighttime "pub crawl" on bike in Windsor, Ontario.
Friday Night Lights is a colourful, nighttime “pub crawl” on bike in Windsor, Ontario.

Also on Friday is our weekly Friday Night Lights. Come to WindsorEats early to enjoy some of the Caribbean Night Party before departing at 8pm on the brightest, most colourful bike ride you’ve ever been on!

The concept of the ride is quite simple. Imagine colourfully lit bicycles rolling by, bells clacking, as they partake in a pub crawl on two wheels. The pack take up the entire street, sometimes stretching several city blocks at a time.

Cost is $6 per person if registered in advance. $10 cash at the ride.

Greenway Jam Music Festival


The Greenway Jam is back from August 11-13 with a great musical lineup!

With 4 different stages setup in and around Kinsgville, Ontario, the festival features artists like Joel Plaskett, The Sadies, the Paul Langlois Band, OKAN, and more!

Tickets are available online and cost between $30 for just Sunday to $100 for the entire weekend.

Dark Sky Night For The Perseid Meteor Shower

Point Pelee National Pak Dark Sky Night
Point Pelee National Pak Dark Sky Night

Need something to do in the late hours after all the food, drink, and music?

Explore the Point Pelee National Park after dark and experience the dark skies with the Royal Astronomical Society of Canada, Windsor Chapter. You will have the opportunity to stay late and see what goes on after dark.

The park will stay open all night August 11 to August 13 for the Perseid Meteor Shower. The best part is, this meteor shower will peak in the early hours of August 12 and 13, making this weekend a perfect viewing opportunity.

The park will open at 6am on August 11 and close at 10pm on August 13.

Street Food Fare!


Get your stretchy pants ready and come with an appetite! WindsorEats is bringing back our Street Food Fare on Saturday, August 12, 2023.

Just like previous years, the Street Food Fare will include not just food trucks, but other food vendors offering gourmet style street food. The Street Food Fare will be held at the WindsorEats location at 400 Erie St. E. and run from 12:00pm to 10:00pm with cocktails and beer being served until midnight.

Read our Ultimate Guide on the 2023 Street Food Fare to learn everything you need to know.

To help support the UHC – Hub of Opportunities (formerly known as the Unemployed Help Centre of Windsor) and the great work they do helping those in need in our community, the event is a pay what you CAN entry. Bring either some canned goods or donate what you’re able to at the door to enter.

The event is pet and family friendly. Confirmed vendors currently include:

  • Rico Taco
  • Vittorio’s Food Truck
  • Zule Eats
  • Dos Green Gos
  • Urban Bites
  • Chef Anthony Dalupan
  • Stelly’s Cuisine
  • The Cheese Bar

Via Italia Bike Races

While you’re in Windsor’s Little Italy taking in some street food, head over and watch the Tour di Via Italia bike races!

Now in its 63rd year, the Tour di Via Italia is the oldest historical, international street race in Ontario. Watch racers from all over North America compete for the largest prize purse in Ontario. It’s truly a unique experience watching and hearing the professional riders zip by.

The races begin at 11:00am with a Children’s Fun Bike event starting at 2:00pm. The main event with the pro racers begins at 5pm!

St. Angela Merici Festival

A street food festival, professional bike races, AND the St. Angela Merici Festival?! Windsor’s Little Italy definitely has to be on your list of places to head to this weekend.

The festival takes place Saturday and Sunday and will be filled with food, live entertainment, a mini street soccer tournament, and to cap it all off,  a candlelight procession that carries a statue of the namesake saint through the streets. It really is like you’re in Italy.

Pride Fest!


View this post on Instagram


A post shared by cait🦋 (@caitlynens_)


It’s truly a weeklong celebration of Pride throughout Winsdor-Essex, but the showpiece is the main festival site, which runs August 11-13 at Lanspeary Park in Windsor, Ontario.

Now in it’s 31st year, the annual Pride Fest Parade will be held Sunday starting at 11am down Ottawa Street and finishing at the main festival site.

The parade route will begin at Ottawa Street and Argyle Road, proceeding down Ottawa Street to Langlois Avenue, turning right on Langlois Avenue to 1250 Langlois Avenue located on the right hand side of Lanspeary Park where the festival take place with entertainment, vendors, food/beverage and much more!

Sandwich Town Market in the Park


View this post on Instagram


A post shared by Sandwich Town BIA (@sandwichtowne)


Cap off the weekend on Sunday with a fun, family event in Sandwich Town.

There will be food, drink, live music, local vendors, free bouncy castles, free games, free face painting, yoga, new Sandwich Town merch, and more! It all takes place in the beautiful, tree covered Paterson Park!

WindsorEats will even be there selling our Italian Cream Sodas!