Whether you’ve visited Windsor or not, you’re probably familiar with some of the stereotypes surrounding it. A former automotive heavyweight. A sleepy border town. And, ahem, a less than flattering review from talk show host, Stephen Colbert, that we just won’t talk about...

But that’s the thing about reputations – they were made to be broken, something Ontario’s southernmost city has been working hard to do. Windsor has seen a rapid revitalization sweep through the city in recent years, bringing with it a growing craft booze scene, a roster of incredible farm-to-table restaurants and an abundance of boutique hotels to relax in post-exploring.

Pizza has deep roots here – and once you taste a slice, you’ll understand why. Thin and crispy, a classic Windsor pizza features canned mushrooms, shredded pepperoni, and ideally mozzarella from the locally made Galati Cheese Company. Road test the hallowed food at Armando’s Pizza or Arcata.

To see the City of Roses’ renaissance in all its glory, head to the Grand Cantina in Ford City. The popular taco joint, decorated with odds and ends from the once-booming Ford Motor Company, is one of many businesses to pop up in the once vacant neighbourhood.

If patties are your thing, head to Motor Burger for homemade ales and bun creations like the Asian-inspired Auto-Banh Mi. Rino’s Kitchen, housed inside a 100-year old building, serves locally-sourced pub grub. Stop for brunch at the Twisted Apron or sip on local brews at Kildare House in trendy Walkerville, the home of Canadian Club and Hiram Walker, producer of J.P. Wiser’s.

Windsor may be the whisky capital of Canada, but more brews abound: Wolfhead Distillery, the first premium craft distillery in Essex County produces small batch spirits like vodka; choose from 30 beers on tap at Craft Heads Brewing downtown; or stay at the Grove Hotel and Brew House, an instagrammable microbrewery in Kingsville.

Windsor Essex, the hottest wine region in Canada, is a grape lovers dream. Head to Sprucewood Shores, Ontario’s only beachside-winery; enjoy freshly caught perch at Oxley Estate Winery; or head to Pelee Island Winery, Ontario’s oldest winery.

There’s plenty to occupy you in Windsor – but even more adventures await in nearby Detroit. Hop over the bridge (or take the tunnel bus) for a chili dog from Lafayette Coney Island and catch a game at one of the Big Four. Time your summer trip right and watch the Ford Fireworks show light up the Detroit River from either side of the water.

Just a four-hour drive or train trip, or one hour flight from Billy Bishop, you can leave on Friday and make it to one of Windsor’s eclectic bars in time for happy hour. ◆

For more information and to plan your trip, head to visitwindsoressex.com