Where to Celebrate Drinksgiving in Windsor

Looking for a new twist for Drinksgiving? Try some of these bars south of the border.
Windsor's Maiden Lane Wine & Spirits opened in 2019. The bar serves classic cocktails, beer, wine, cider and small plates. // Photograph by Rebecca Simonov

Quick — think of one of the most diverse neighborhoods in metro Detroit. One where more than 1 in 4 residents were born in another country and there’s a booming nightlife. What did you think of? Hamtramck? Ann Arbor? Troy?

What about Windsor, Ontario? Our neighbor to the south prides itself on its multiculturalism. Numerous different groups bring a wealth of cultural influences to the drinking and dining scene in the city of 313,700. Add to this a historic rum-running tradition and the largest whisky distillery in North America. If a jaunt over to Windsor isn’t on your to-do list yet, it should be.

Adriano Ciotoli at WindsorEats knows a thing or two about the drinks scene in town. He founded the group in 2004 as an online dining guide, and since then, his company has evolved to cover bike and scooter tours, bar hops, and a dive bar crawl from Windsor to Detroit.

In 2022, WindsorEats got its very own space, a no-frills but eminently Instagrammable spot in the city’s historic Little Italy. The venue has themed events, which have included Ciotoli’s dog’s Sweet 16 party, Caribbean Nights, a Taylor Swift-themed extravaganza, and regular occurrences like trivia nights. A bar menu filled with what Ciotoli calls “approachable craft cocktails for individuals” includes margarita and mojito flights.

The Windsor approach to drinks is familiar to Detroiters used to laid-back Midwest sensibilities.

“High-end cocktails that have 17 different ingredients can be intimidating to a lot of people that don’t normally go out for a drink,” Ciotoli says. Most Windsor bars, even if they’re billed as craft cocktail spots, are “very laid-back, very approachable, so it’s not something to be afraid of. We’re Canada’s south, so that’s our Southern charm.”

Traditional taverns are a part of drinking culture in Windsor. Operating as a hotel since 1859 and a tavern since 1878, Dominion House is an old-school roadhouse with a storied past of rumored Prohibition-era rum-running.

Victoria Tavern is a cozy wood-lined neighborhood bar with darts and live music; it’s where Henry Ford signed the contract in 1904 to begin manufacturing in Canada.

Among Windsor’s elevated craft cocktail bars, Maiden Lane Wine & Spirits is a relative newcomer, arriving on the scene in 2019, but it quickly cemented its reputation by serving up classics like the aviation, vieux carre, and paper plane alongside creative and balanced house inventions and a full wine selection.

WindsorEats offers a dive bar crawl from Windsor to Detroit. Its drink menu includes margarita and mojito flights. // Photograph by Rebecca Simonov

Drinks can be consumed on-site or ordered for takeout. Blind Owl is similarly crafty with a rapidly rotating cocktail menu and eye-popping drinks.

F&B Restaurant set the standard for craft cocktails in Windsor during the the cocktail revival and has expanded its empire. The F&B Hospitality Group now has three more spots: The Grand Cantina and Funky Chow Kitchen on the same street (Wyandotte) and Taloola Café on Devonshire Road.

At Windsor’s cocktail bars, bartenders are drawing from their multicultural backgrounds as inspiration for drinks. Think espresso martinis with mole sauce-infused vodka; cocktails made with arak, a Middle Eastern spirit; and drinks celebrating Niagara wine or Italian aperitivos. Recently, a surge of Ukrainian immigrants has added to the ethnic mosaic that informs the drinks scene in Windsor.

“It’s all those little things that are happening across the world that you think are in some faraway land but are actually influencing our little pocket of the world,” Ciotoli says.

Another immigrant of sorts to Windsor, albeit a historical one, has had an oversize influence on the beverage landscape of the city.

Walkerville, a historic neighborhood and popular nighttime spot, was founded by Detroiter Hiram Walker in 1858 when he moved his whisky distillery across the river to take advantage of laid-back liquor laws, later changing the brand’s name to Canadian Club. Today, Walkerville is home to the largest distillery in North America and a burgeoning drinks scene.

Tours of the historic Hiram Walker & Sons Distillery, run by the J.P. Wiser’s Experience, offer visitors a chance to sample and shop for rare and legacy-release whiskies. Several nearby bars and breweries round out the experience in the historic district.

Like Walker, who moved his business to Windsor but took the ferry from his Detroit home every day, many Windsorites and Detroiters consider the border a formality rather than an obstacle.

“We look at Detroit as a neighborhood of Windsor,” Ciotoli says. “Detroit is a massive part of life in Windsor.” For smart and adventurous Detroiters looking for a new set of classic hangouts, Windsor should be the next neighborhood hot spot.

This story is from the November 2023 issue of Hour Detroit magazine. Read more in our digital edition