8 Things That Prove Toronto Is the Coolest City

Kensington Market

Multicultural and vibrant: These are the best words to describe Kensington Market, a must-experience neighborhood in the heart of downtown. Officially a National Historic Site of Canada and a protected area, Kensington was once an immigrant enclave in the bustling city. Now it's a center for the still-thriving counterculture of Toronto (think Haight-Ashbury, but much colder than San Francisco). In the cramped but tidy streets, you'll find vintage shops, record stores, independent cafes, ethnic grocers, and head shops. Pedestrians mill on the sidewalks and in the streets during festivals, including a colorful Kensington Karnival to ring in the winter solstice.

Some of my picks in this amazing neighborhood are Courage My Love (high-quality vintage clothing for all genders), Moonbean Coffee Company (a micro roastery and hangout), Graffiti's (a tiny rock bar with a black-metal brunch), and Sanagan's Meat Locker (hipster butcher extraordinaire).

Canadian Cuisine

Toronto is undeniably diverse, and its culinary scene reflects the influence of hundreds of immigrant groups who brought cheap, hearty, and delicious fare to the cold continent. But, like many other places I've traveled to lately, Toronto seems to be in the midst of rediscovering its homegrown ingredients and culinary roots—beyond maple syrup and poutine, of course. The city's chefs have taken to local produce, fish, and game, exploring ancient techniques like fermenting and smoking while updating Canada's distinctive heritage dishes.

The fine-dining scene is dominated by restaurants like Canoe, with tasting menus that focus on one particular regional cuisine and feature components like Lake Manitoba trout, Saskatoon winter berries, and Northern Woods mushrooms. Similarly, modern Marben, with its bespoke cocktails and local ingredients in an eclectic around-the-world menu, is right on trend. Both are worth a visit.

And if you want to go way down-market, the Carousel Bakery at St. Lawrence Market is the only place to experience a true Toronto original: a peameal bacon sandwich. Get in line early, choose a mustard, and enjoy.

Toronto Islands

Despite the frigid weather, Torontonians are an outdoorsy bunch, and they take to the Toronto Islands, a small chain just offshore, to experience some of the best urban green spaces in North America. These public islands have awesome views of the glittering city skyline on one side and the equally glittery Lake Ontario on the other. Centre Island, the largest, is just an inexpensive ferry ride away from downtown. From the dock, visitors can rent bicycles to explore the island's many trails; in summer, canoes and kayaks are available to rent for paddling the surrounding lake. On the island, you'll find a small amusement park, beaches, picnic areas with fire pits, and cafes. (Note that Hanlan's Point Beach is clothing-optional!) If you're not feeling the outdoors, a small artists' community at Gibraltar Point houses studios for painters, sculptors, and other creative types; it makes for a fun cultural side trip.

Distillery District

This neighborhood of Victorian industrial warehouses and quaint street signs looks flat-out Dickensian—but thoroughly updated. Since being named a National Historic Site in 1988, the Distillery District has become a shopping-and-nightlife hub for hip locals. It's now home to Toronto's cozy Christmas Market, at which patrons can sip mulled wine, browse artisans' stands, and gather around for carols. Year-round, a collection of boutiques and restaurants brings visitors day and night (I recommend Brick Street Bakery's sweet and savory pastry or Mill Street Brew Pub's award-winning beers and patio). Gallery space and performance theaters add to the artsy but un-self-conscious vibe. Bring your best skinny jeans.

Chinatown(s)

Many cities claim a Chinatown, but the greater Toronto area has seven. The district on Spadina Avenue around Dundas Street West, commonly referred to as Old Chinatown, is one of the best places in the world to experience Thai, Vietnamese, and countless Chinese regional cuisines all at once.

Insiders say the best times to try out Chinatown are late at night, after the bars close and when your stomach is crying out for cheap and tasty eats, and early on weekends for world-class dim sum. At any time, Toronto's dumplings and soup buns (xiao long bao, or XLBs) are legendary, with places like Mother's Dumplings, Rol San, and Asian Legend serving up exemplary springy buns filled with hot broth. (Pro tip: Poke the top with a chopstick to slurp out the soup.) Relative newcomer Rosewood Chinese Cuisine gets my pick for the following magical words: all-day dim sum. Each dish costs just $2.20 CAD on weekdays, making this one of the best dining deals in a pricey town.

Bloor-Yorkville

This glam Toronto neighborhood continually ranks among the world's best for shopping, so if you're looking to blow your budget (or if you don't have one), Bloor-Yorkville is the place to go. Here you'll find high-end hotels like the Four Seasons, the city's best spas and salons, and storefronts from Chanel, Michael Kors, and Louis Vuitton. You can shop Canadian labels like Holt Renfrew and Harry Rosen, check out local and international art at ritzy galleries, or sip cocktails at a rooftop bar. I think the best way to experience this posh area is free: Just park it on a bench and people-and-Maserati-watch at your leisure.

Queen West

Both Vogue and Lonely Planet dubbed Queen West Toronto's coolest neighborhood in 2014, and it's hard to argue that this one-mile stretch could be anything but. Neat rows of art galleries, studios, design houses, boutiques, restaurants, and bakeries line Queen West, a former industrial neighborhood that's taken well to its newfound fame. Street-art addicts will love Graffiti Alley, where spray-painted murals are totally legal. The fashionable set will love the fabric stores, bead and button shops, and indie-label boutiques. And everyone can enjoy the artsy hotel The Drake, where a rooftop bar offers some of the city's best views and nightlife—and where you might spot a celebrity or two.

Art Gallery of Ontario (AGO)

The architect Frank Gehry is a Toronto native, so it only makes sense that when this city institution needed a refresh, Gehry came to the rescue. A $276 million renovation later, and AGO is now renowned not just for the art it contains but for its own modern, airy architecture. Many experts contend that its wide-open spaces are among the world's best for viewing artistic masterpieces, with a billowing glass exterior and a sculptural wooden staircase that Gehry hoped would inspire visitors to fall in love. The museum's collection certainly inspires passion, from its permanent Canadian works by the Group of Seven to rotating exhibits by Basquiat, Michelangelo, and so forth. If you visit, plan a full day and build in a coffee break at the fifth-level Galleria Italia espresso bar (the views of the city from the undulating wood-framed windows are stunning).

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