Ours to Discover

Ours to Discover: Windsor

A winter weekend in Canada’s southernmost city, With its rich history, creative cuisine and picturesque waterfront, Windsor offers road trippers more than meets the eye.

By Jessica Huras Wheels.ca

Jan 22, 2022 5 min. read

Article was updated 4 months ago

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About this series: Wheels wants to inspire you to get ready to explore — but only if COVID-19 conditions make it safe to do so. This series of daytrips and longer drives highlight great experiences you can have in the province, ands show you why Ontario is “Ours to Discover.”

As a city best known for its link to Canada’s automotive industry, Windsor may not be the most alluring road trip destination. Scratch beneath its industrial surface, however, and you’ll find a vibrant city with an up-and-coming culinary scene and mild winter weather thanks to its location near Ontario’s southernmost point. Here’s how to make the most of a two-day getaway to Canada’s border town.


In the morning: Windsor can be reached in about four hours following a straight-shot southwest down Highway 401. If time allows, consider taking the longer, scenic route along Highway 3, which traverses the pleasant Lake Erie shoreline. Another option is to take Highway 2 once you hit Kitchener-Waterloo to swap bland highway scenery for bucolic Ontario farmscapes.

In the afternoon: Kick off your Windsor weekend at Armando’s Pizza and get a taste of the city’s most iconic contribution to Canada’s culinary landscape. This long-running restaurant is one of several local joints specializing in Windsor-style pizza, a distinctive thin-crust pie with eyebrow-raising (but delicious) toppings that include canned mushrooms and shredded pepperoni.

Ours to Discover

After getting your ’za fix, learn about Windsor’s role in shaping the Canadian whisky industry at the Hiram Walker & Sons Distillery. Sign up for a guided tasting to sample some of the many whiskies produced at this landmark facility.

Save time to wander around the surrounding Walkerville District, a historic neighbourhood where heritage buildings meld with modern shops, restaurants and bars. Stop by the Urban Art Market to hunt for made-in-Windsor souvenirs or check out the local artwork on display at the Walkerville Artists Collective.

In the evening: Stop at your hotel for a pre-dinner refresh. For a classic and relaxing stay, opt for A Hidden Gem Bed and Breakfast, which is set amid Walkerville’s atmospheric streets. Or, if you prefer a name-brand hotel with a view, try the Holiday Inn Express Windsor Waterfront, where many rooms overlook the Detroit River skyline.

Afterwards, head to hotspot Gladstone Commons (or opt to order out and enjoy at your hotel) for seasonal small plates paired with nano brews and inventive cocktails. Helmed by chef Dana Friis – who previously worked at Vancouver’s Cioppino's Mediterranean Grill — Gladstone Commons’ ever-changing menus are thoughtful but approachable. Expect dishes like bison short ribs with wild mushrooms or butternut squash agnolotti.

Swing by cosy cocktail bar Blind Owl for after-dinner drinks. Blind Owl draws inspiration from Windsor’s rum-running history for its imaginative cocktails and “hidden” entrance.


In the morning: Start your day right with breakfast at the Twisted Apron, a much-loved restaurant known for its playful, homestyle fare. Take a post-breakfast stroll through Old Sandwich Town, one of Ontario’s oldest settlements. Here you’ll find a number of significant historic buildings, including the Sandwich First Baptist Church, which was established by former slaves who arrived in Canada via the Underground Railroad.

Ours to Discover

In the afternoon: Time to refuel at Mamo Burger Bar, a casual spot known for its local beef patties which are freshly-ground onsite every day. Next up is the Art Gallery of Windsor, which is set in a lovely waterfront location. The gallery features more than 4,000 pieces of contemporary art, spanning from painting and photography to multimedia installations and sculptures, with a focus on Canadian works. QR codes placed throughout the gallery will guide you to some of the highlights.

Ours to Discover

In the late afternoon: Before heading back to Toronto, bundle up for a walk along the city’s five-kilometre riverfront trail, which offers attractive views of the Detroit skyline. You’ll pass through Dieppe Gardens, which is home to the Spirit of Windsor, an early 20th-century steam locomotive that now stands as a tribute to the Canadian railroad industry. See more than 30 large-scale outdoor sculptures at the Windsor Sculpture Park, which is located close to the beginning of the trail near the Ambassador Bridge. Warm up with a hot drink and a snack at Anchor Coffee House, a cafe that sources its beans from various Canadian coffee roasters, and then hit the road.

Ours to Discover

COVID-19 need to know

Ontario is currently in a modified Step 2 of its “roadmap to reopen,” with indoor dinning banned. Some attractions may be closed or operating at a reduced capacity. Consult the Windsor-Essex County Health Unit for the most up-to-date information and contact individual businesses ahead of your trip to confirm how they’re currently operating.

For the drive

Create a road trip playlist featuring tunes from some of the notable musicians to emerge from the City of Roses. Progressive rock band The Tea Party was formed in Windsor in the 1990s. For a different homegrown vibe, you can also add the music of country-pop singer Shania Twain and R&B artist Tamia.


TIMELINE: Drive guide

Day one

  • 8 a.m. Depart Toronto

Drive southwest on Highway 401

Take Exit 13 for Dougall Parkway

  • Noon Lunch at Armando’s Pizza

  • 2 p.m. Hiram Walker & Sons Distillery

  • 3 p.m. Walkerville District

  • 6 p.m. Gladstone Commons

  • 8 p.m. Blind Owl Bar

Day two

  • 9 a.m. Twisted Apron

  • 10:30 a.m. Old Sandwich Town

  • Noon Mamo Burger Bar

  • 1 p.m. Art Gallery of Windsor

  • 3 p.m. Riverfront Trail

  • 4:30 p.m. Anchor Coffee House

  • 5 p.m. Drive back to Toronto