48 Hours in Windsor: A Guide to Ontario’s Most Underrated City

Windsor honestly surprised me. Before this trip, I mostly knew it as the city across the river from Detroit, but after spending a weekend exploring, I quickly realized there’s so much more to the city. From historic neighbourhoods and beautiful architecture to an unexpectedly great food and drink scene, Windsor is an underrated destination that deserves a spot on your Ontario travel list.

If you only have 48 hours, here’s everywhere I’d recommend adding to your Windsor itinerary. Click here for some highlights from the trip!

Chance Coffee

Start your morning at Chance Coffee, a cozy local café that’s perfect for grabbing a coffee and something to eat before exploring the city. It’s a great first stop before making your way through the surrounding neighbourhoods.

Ford City

After coffee, take a walk around Ford City and check out the colourful murals throughout the neighbourhood. The area has a fascinating connection to Windsor’s automotive history and is a great place to explore on foot.

Nauti V’s

For lunch, head to Nauti V’s, where you’ll find a seafood-focused menu and a laid-back atmosphere. The Caesar oysters were a standout for us.

Willistead Manor

Just a short walk away is Willistead Manor, a stunning 120-year-old historic home surrounded by beautiful grounds. The manor offers guided tours in July and December, making it a great stop for anyone who loves architecture and local history.

Walkerville Brewery

Next up: beer! Walkerville Brewery has more than 140 years of history in Windsor and is a must-visit for craft beer fans. Grab a flight so you can sample a few of their brews.

WindsorEats

For dinner, head to WindsorEats, a huge outdoor patio and food truck destination that brings together drinks and food from local vendors. The margaritas alone are worth the visit—the flavour combinations are some of the most creative I’ve tried. And make sure to grab tacos from Rico Taco while you’re there! Our birria tacos were incredible.

Art Windsor-Essex + Chimczuk Museum

On day two, start with two museums under one roof. The Chimczuk Museum takes you through the city’s history, including Windsor’s role in the Prohibition and the Underground Railroad, while the floors above house an art gallery. Don’t miss the third-floor terrace, where you’ll get an amazing view of the Detroit skyline.

Sandwich Brewing Company

For lunch, make your way to Sandwich Brewing Company for another local beer flight and a delicious sandwich. It’s located in Windsor’s historic Sandwich Town neighbourhood, making it an easy stop while exploring the area.

Duff-Baby House

Just around the corner, you’ll find the Duff-Baby House, a roughly 200-year-old historic home that survived the War of 1812.

Streetcar No. 351

For an afternoon treat, stop by Streetcar No. 351, a restored streetcar dating back to 1918. The historic vehicle has been given a new life, with a café beside it where you can grab a sweet treat.

Whiskeyjack Boutique

If you want to do a little shopping, Whiskeyjack Boutique is a great place to browse locally inspired finds and pick up a souvenir to remember your trip.

WIFF Alley

Next, take a walk through WIFF Alley, a colourful outdoor space filled with murals and street art. It’s a great spot to snap a few photos while exploring downtown Windsor.

Cucina 360

For your final dinner in Windsor, head to Cucina 360 for Italian food in a warm, inviting setting.

Maiden Lane Wine & Cocktail Bar

End your weekend with a cocktail at Maiden Lane Wine & Cocktails, a stylish cocktail bar known for its creative drinks and intimate atmosphere. It’s the perfect final stop before calling it a night.

Final Thoughts

After 48 hours in Windsor, I left genuinely surprised by how much the city has to offer. There’s a little bit of everything here—history, art, architecture, local food, craft beer, cocktails, and plenty of walkable neighbourhoods to explore. Click here to see a full recap of the trip!

And if you’re travelling from Ottawa, getting there is easier than you might think: Windsor is just a 1 hour and 45 minute flight from Ottawa with Porter, making it a very doable option for a quick weekend getaway.

If you’re looking for an Ontario city that feels a little different from the usual weekend destinations, I’d definitely put Windsor on your list.

Original Blog Post by theottawadiaries