The best places to eat and drink in Windsor this fall

This fall we're going south to Windsor, Canada's southernmost city, for the ultimate city escape. With the country's warmest wine growing region and its very own homeslice, you better bring your appetite.

Just a three hour drive from the GTA, Windsor Essex is the ideal fall spot to relax after a long week of laggy zoom meetings and microwave meals. It’s an up-and-coming foodie destination, a fine wine weekend getaway and an outdoor oasis with plenty to keep your eyes and belly full.

It’s no wonder the Essex Pelee Island Coast, with its abundant grape growing soil and long hours of sunshine, has acquired the EPIC nickname for its remarkable wine experiences. Trek along the same latitude as Northern California and Tuscany (did someone say wine o'clock?) to discover notable wineries like Cooper’s Hawk Vineyards and Pelee Island Winery. Then get off the beaten path and check out lesser known gems like Black Bear Farms in Kingsville. Whether you drive, bike or ferry to the vines, you'll be sure to work up a thirst on your grape escape.

Windsor is the birthplace of Canadian whisky, so making alcohol is more than a trade, it’s tradition. Canadian Club, the whisky that started it all, was created by Detroit Business man Hiram Walker who first opened a Windsor distillery in 1858. Today Walker's legacy lives on in the new generations of craft breweries and distilleries all over town.

Fall favourites for Windsor imbibing 

Lola Blush Sparkling Rosé

The best places to eat and drink in Windsor this fall | Lola blush Sparkling Rosé

Pelee Island Winery’s Lola Blush Sparkling Rosé is an Ontario Wine Awards gold medal winner and first place in our hearts. With over 700 acres of vineyards, Pelee Island Winery is the largest private estate winery in Canada. You can also check out their Kingsville winery location for tours and tastings.

Walkerville Brewery 

The best places to eat and drink in Windsor this fall | Walkerville Brewery Honest Lagger

From microbreweries to hand crafted, small batch brews, craft beer is taking over. Check out Walkerville Brewery which operates in one of whiskey tycoon Hiram Walker’s original buildings. Their easy drinking 'Honest Lager' is honestly crushable.

Hiram Walker & Sons

The best places to eat and drink in Windsor this fall | J.P. Wiser's old fashioned whisky cocktail

Windsor and whisky go hand-in-hand. Hiram Walker & Sons is the largest distillery in North America and produces iconic Canadian brands like this J.P. Wiser’s Old Fashioned which already has all the fixins' ready to drink.

Sprucewood Shores Estate Winery 

The best places to eat and drink in Windsor this fall | Charcuterie and wine on the beach at Sprucewood Shores Estate Winery

Nothing beats a beach picnic, especially at Sprucewood Shores Estate Winery, Ontario's only beachfront winery. Tuck into a bottle of Lady in Red along the shores of Lake Erie. No need to pack a cooler, the wine comes with the place.

 Fall favourites for Windsor dining 

You'll never run into the problem of drinking on an empty stomach with the abundance of farm-to-table dinning and artisanal makers. Cut into some stinkingly good Canadian made cheese from the Cheese Bar in Lakeshore and never eat the same thing twice at Oxley Estate Winery where the menu changes based on what’s available at farmer's markets.

Better yet, pick your own produce at Chappus Farms and the best berries ever from Raymont's Berries. If you need to mix in some water, go for a Cedar Beach dip or rent a paddle board at Lakeview Park West Beach

At the end of a long day of eating and imbibing, tuck into your temporary home away from home – a wine barrel airbnb, perhaps? – and watch the sun slowly start to sink around 9 p.m. Make sure you catch it and raise a glass to a day well spent.

Wolfhead Distillery

The best places to eat and drink in Windsor this fall | drinks at Wolfhead distillery

The leader of the pack when it comes to a premium craft distillery. By incorporating local ingredients from Windsor Essex, Wolfhead Distillery creates truly one-of-a-kind, small batch vodka and whisky. Just like their spirits, their newly opened restaurant and sprawling patio have that same farm-to-table approach. The ground chuck burgers have amassed quite the pack following and their whisky isn't just for their grain-to-glass cocktails (hello, whisky smoked ribs). The perfect chaser? An ice cream and a waterfront stroll in the charming nearby town of Amherstburg.

Via Italia

The best places to eat and drink in Windsor this fall | lamb at Mezzo Ristorante

We absolutely amore Windsor's Little Italy which lights up Erie Street with the delightful tastes and smells of Italia. Our trip wouldn't be complete without a visit to Mezzo Ristorante. We're still dreaming about their goat cheese bruschetta and rosemary and oregano marinated lamb with a wild mushroom and pancetta risotto. And that white truffle oil – bellissimo. Their newly opened patio overlooks the entire piazza – errr, street, where you can bear witness to all the vibrant, Nonna-aproved, carb-loving specialty shops, stores and cafes.

Shawarma City

The best places to eat and drink in Windsor this fall | A shawarma to-go

This Middle Eastern snack has found a second home in Windsor – aka the shawarma capital of Canada – where Levantine bites abound. Beneath the warm pita, you’ll find expertly seasoned, tender, marinated meat like lamb, veal, or beef with fresh and pickled vegetables, tahini sauce and a whole lot of love. One of the best things (and there are many) about shawarma is that you can have it at any time of day. Our favourite spots for the slow-roasted meat cones are Hamoudi's Shawarma and Shawarma Palace.

Pizza, pizza and pizza

The best places to eat and drink in Windsor this fall | fresh out the oven pizza

In Windsor, pizza is life. It has its very own style similar to New York’s except the medium thick slices make the delicious toppings stick together for one glorious mouthful. Try iconic Windsor toppings like shredded pepperoni, canned mushrooms (it's a thing), oregano sauce and, of course, mozzarella cheese made by Galati Cheese Company. Some Windsorites have been known to freeze entire pizzas in case of an emergency shortage. For a slice of the OG, you can't miss Caboto Club or Arcata. For new takes on the classic, try Oven 360 and Armando’s.

To start planning your trip, head to