windsor ontario

How to spend 48 hours in Windsor Ontario

Windsor may be way down south for residents of the GTA, but the city is right on the axis of a major cultural hub. "The Rose City" provides an unusually warm climate for Canada, making it a great place for patio season and it's a quick trip down by train or car. 

Here's how to spend 48 hours in Windsor, Ontario.

10 a.m. - Rent a bike from Bike Windsor Essex or hop on one of Windsor's new Bird scooters

Bike Windsor Essex's advocacy group has done wonders for Windsor streets by adding a ton of bike lanes and educating drivers and cyclists alike on road safety. Windsor now has safe rideable streets to get you from neighbourhood to neighbourhood. 

Located in midtown, Jackson Park is full of over 10,000 plants, historic monuments (including two World War II air force monument replica planes), fountains overlooking a lush sunken garden, sports fields and many lawn and picnic table areas.

If having biked from Bike Windsor Essex in Walkerville, take Windsor’s main street of Ouellette right down to the riverfront and take the scenic route along the riverfront trail back to Walkerville.

12 p.m. - Lunch in Historic Ford City

Hold onto your scooter or bike and enter Ford City. Windsor is known as the Automotive Capital of Canada so it's no surprise that one of our core neighbourhoods is named after the major manufacturer.

Down the main street of Drouillard you’ll find many hidden gems. One of them being Heimat, a traditional German biergarten with a full menu of traditional food items.

1 p.m. - Shop local

After you've filled up on schnitzel and Helles, browse Ford City’s new shops! Wolf and Rebel is your destination for self-care items and a curated selection of vintage and thrift pieces often guest-curated by artists around the city.

Bunch is your destination for specialty gift items and quirky curiosities! 

3 p.m. - Last round for a while

Before you check into your Airbnb you may have time for one more round…Check out Chapter Two brewery which straddles the border of Ford City and Walkerville. 

Appropriate for Ford City, Chapter City has a trendy garage vibe. Be daring and try the 'Zug Island Porter' … maybe just don't ask what or where Zug Island is.

4 p.m. - Check-in for Overnight Stay in Windsor's Prominent Walkerville Area

Known for the buildings designed by Albert Kahn, and most notably, the Hiram Walker row houses on Monmouth, Walkerville is a quiet yet vibrant neighbourhood filled with shops, bars, eats and beautifully walkable streets and parks.

This new and stylish Airbnb, for example, is situated right in Olde Walkerville and borders Ford City. 

7 p.m. - Drinks and dinner at Funky Chow

Funky Chow Kitchen (FCK) is one of Windsor's newest and most popular dining destinations, right in Olde Walkerville.

Funky Chow popped up during lockdowns and soon had its own home under the Blackburn Radio station. Serving inventive Asian-fusion with fresh classics like oysters, FCK offers up a buzzing atmosphere and great cocktails to pair with any dish.

If you're ever in need of a quick bite in Walkerville or looking for something more casual. Slices is Windsor's hottest new pizza destination. It provides a fun atmosphere, friendly staff and pizza that is amazing from tip to crust. 

10 p.m. - Late night drinks and fun

Along with being "The Rose City" and "Automotive Capital of Canada," Windsor is also known as, "Sin City." But if gambling isn't your thing, you can find a few gems in the form of historic dive bars.

The Victoria Tavern is located just around the corner from Funky Chow and keeps its treasure well hidden.

If you go through the door next to the bar, you'll find a spacious hidden patio tinselled in fairy lights.

Whether you grab an OV or try something a little more crafty, you're sure to spark conversation with Windsor's finest locals. This watering hole attracts artists, musicians and local business people alike. It's one of Windsor's favourite dives.

Day 2
10 a.m. - Breakfast in Little Italy

TOAST is one of Windsor's busiest brunch spots. They have a delectable sweet or savoury menu with massive portions - so come hungry. They do usually have quite a wait so if you can bear it, getting there even before 10 a.m. might be a good call.

11 a.m. - Stroll down Erie St. 

Before you head out of Windsor's Little Italy, be sure to stop in their many bakeries and specialty food shops for some take-home items. 

Whether it be pasta, cannoli or prosciutto from La Stella Supermarket, Erie St. has every Italian specialty you can think of. If you're not full yet… stop at Gennaro's for some superb gelato!

1 p.m. - Explore your natural surroundings

Little known to travellers through Windsor, the huge attraction for local trail walkers and runners alike is the Ojibway Nature Centre and Prairie.

Located to the west side of the city, this hidden forest and prairie boasts beautiful nature paths and trails.

On your walk you'll usually see deer, rare birds of Ontario and chipmunks. In the prairie there can be a snake or two but the guides at the Nature Centre can help you identify where and what you might see.

5 p.m. - It's pizza time

Before heading out of the city, you must try what all Southern Ontarians won't stop talking about… Windsor Pizza.

Some will say it's the shredded pepperoni, some will say its the Galati cheese - and you may have seen the headlines about Windsorites spending upwards of $600 to fly their native pizza out to relatives in British Columbia.

There is a great debate on which of Windsor's long-standing pizza joints takes the pie, and it seems as though each neighbourhood has their own winner.

While I don't want to start any fights here, you are already near South Windsor, which is close to the 401, and so it might be worth it to grab a South Windsor slice on your way out.

It really just depends on who answers their phone first. Take your pick between Capri PizzaArmando's Pizza South WindsorArcata Pizza or Antonino's Pizza.

Lead photo by

G.V. Chana. Writing by Alexandra Sellick.


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