Windsor's Delicious Secret: A Pilgrimage to Canada's Pizza Capital

The air this weekend is cool and crisp, indicative of a true Canadian autumn—the kind that bites just enough to make a perfectly timed escape from the city feel like a necessity: a road trip to Windsor which, I have come to realise, holds a very particular, very compelling secret.

For me, this latest trip is less about the casino lights or the trans-border views, and entirely about a deep dive into an idea that has been brewing for over a year: a taste of the legendary Windsor pizza scene—the self-proclaimed “pizza capital of Canada” with its unique style: shredded pepperoni, canned mushrooms, and Galati Cheese, a cheese manufactured in Windsor. It is a thing of local pride, a culinary idiosyncrasy I simply must understand.

My mission began not in the city centre, but in the quaint historical streets of Amherstburg. A Friday afternoon felt perfectly utilised by a stop at Wolfhead Distillery. I settled in for a tasting flight of their craft spirits, a gentle, warming initiation into the Essex County terroir. I was especially taken with the seasonal favourites, the rich Pumpkin Spice Cream and the fiery kick of the Apple Pie Moonshine.

With the chill of the fall air firmly kept at bay, a necessary stroll through the property was in order, including a quick stop to admire the sheer scale of the property: over 90,000 barrels stacked for as far as the eye could see.

Then, before even reaching the city core, the mission hit its first pizza stop: Nikki's Pizza. This unassuming food truck delivered my very first taste of Windsor's magic—a delicious slice that immediately validated the entire pilgrimage. What struck me most was the brilliant interplay of the toppings. The signature shredded pepperoni was the star, its edges blackening in the oven to give a concentrated, charred flavour that I hadn't expected but instantly loved. It was a perfectly balanced slice—a powerful, savoury experience that confirmed every good thing I had heard about Windsor’s pizza.

The evening’s main event was dinner at Armando’s Walker Road. Known as one of the pioneers of the Windsor style, the meal lived up to the quiet, confident local hype. Upon receiving the pizza, the first thing I noticed was the crust, which was perfectly baked—crisp on the outside yet beautifully soft inside. It was here, gazing upon the signature shredded pepperoni, that I truly began to understand the style. I even had the pleasure of meeting Andre, Armando's son, who enthusiastically described how the pizza is still made in its traditional hand tossed way, and it absolutely showed.

Later, on the drive back to Caesars Windsor (our home base for the weekend), a quick pit stop for a late-night slice from Cheese Wheelz served as a necessary stop. This particular slice delivered exactly what you want after a night out: a satisfyingly greasy but tasty piece of comfort food, complete with deliciously charred edges that added just the right amount of crunch and smoky flavour. Staying at Caesars Windsor on the riverfront is the perfect counterpoint to the city’s quiet exploration, offering a sleek, high-energy retreat to recharge between slices.

Saturday brought a necessary adventure: exploring the bustling, artistic heart of the city. Starting with a solid, unpretentious breakfast at the Twisted Apron, the day kicked off with truly delicious fuel. The meal was a complete success, and I may have had the best breakfast sandwich of my life right there—a perfect blend of fresh, high-quality ingredients that was anything but ordinary.

After a delicious breakfast, I walked it off in the historic Walkerville neighbourhood. This area is a delightful contradiction of grand old architecture and hyper-modern independent retail. My favourite discovery was Walkerville Relics, which was my ideal kind of antique shop. Rather than a chaotic jumble, every piece was perfectly picked and curated. The inventory was exceptional, and I ended up buying quite a few things, including a fantastic antique rattan chair. I also enjoyed the unique gifts at Jones & Company. The energy of the area is infectious, a vibrant pulse that suggests a town not just surviving, but truly flourishing.

The afternoon was a masterful exercise in pizza sampling. This leg of the culinary mission began with a mandatory stop at the unassuming Krusty's. Stepping inside was a pure shot of nostalgia; the joint felt wonderfully retro, as if it were around since the '90s.

If you're serious about the local style, you simply have to get the Krusty's slice ‘dirty’, which means brushed liberally with garlic butter—a beautiful, greasy, shredded-roni masterpiece. The sheer size of the slice alone confirmed why it’s a local legend.

To keep the momentum going, I snagged an excellent lunch combo nearby: a slice from OG Pizza, which distinguishes itself with its focus on fresh, local ingredients and a signature thin, stone-baked crust—paired perfectly with a mid-day flight of craft beer at Chapter Two Brewing. This was followed by another necessary stop for a palate cleanser at Sandwich Brewing Co., a crucial ritual before the day's final feast.

The culmination of the day’s work was dinner at Spago, a local favourite that shows the Italian influence on Windsor’s dining scene extends far beyond the humble pizza. The meal itself was a welcome respite from the intense pizza mission. I indulged in their seafood pappardelle, which was absolutely delicious—a rich, flavourful plate of perfectly cooked fresh pasta and seafood that provided a necessary and wonderful break from the world of mozzarella and cornmeal crusts.

But even after such a satisfying meal, the urge for one last slice was undeniable. A late-night, final slice from Sam’s, a pizzeria particularly popular with the university crowds, before collapsing back into the hotel bed was a mandatory capstone. The differences between the slices are sometimes subtle, yet distinct—a testament to the fierce, almost tribal loyalties these neighbourhood joints inspire.

Sunday was reserved for the kind of quiet reflection only an excellent breakfast at Lumberjack can provide, followed by a cultural reckoning at the Windsor Sculpture Park.

Walking the waterfront, tracing the city's stunning collection of large-scale outdoor art, one realises the scale of Windsor’s cultural ambition. The city is a lovely, surprisingly verdant collection of parks, the Detroit skyline shimmering across the river as a constant, beautiful backdrop. After the park, I made sure to visit Streetcar 351, which holds significant historical value to both Windsor and Canada, serving as a powerful reminder of the city's past transportation links and its industrial heritage.

The pilgrimage concluded fittingly: a final, solemn lunch back in the pizza heartland at Antonino’s South Windsor location. It was here I got an incredible behind-the-scenes tour and had the pleasure of meeting the owner, Joe (son of founder Antonino). His dedication and passion for Windsor-style pizza were absolutely infectious. He spoke about the history, the ingredients, and the community loyalty with such fervour that I left convinced he should seriously write a book documenting the entire delicious regional phenomenon. It was the perfect, passionate capstone to my journey.

I came to Windsor for the pizza—and it lived up to the hype, forcing a re calibration of what a regional pizza style can be. But I leave with something more profound: a deep appreciation for an Ontario city with distinct, un-flashy confidence, a vibrant network of independent businesses, and an architectural history that is stubbornly, wonderfully preserved. Windsor, it turns out, is a place where every corner tells a story, and every slice suggests a fierce, delicious, local pride. It is, quite simply, a fall weekend that should be required reading for any serious Canadian traveller.