Toronto neighborhoods to explore this winter

Toronto is one of the planet’s most ethnically diverse cities – a creative, harmonious convergence of histories and cultures. All are welcome and supply meets demand – whatever floats your boat, you’re bound to find it here.

Easygoing locals, united by their love for this city, embrace Toronto's epic winters, and an aging public transit system and traffic mayhem, to get along pretty well all things considered. So take a page from their book and explore the flavors and aromas of Toronto’s myriad friendly neighborhoods despite the sub-zero temperatures this winter.

Toronto's size and a habit of constantly re-inventing herself makes it hard to get to know the Big Smoke in a short period of time, but we’ll give you a tip: take a neighborhood on as its own mini-adventure and get to know what really makes Torontonians tick.

Yonge and Dundas

First get your bearings at Yonge-Dundas Square, the unofficial center of downtown, just south of the Bloor/Yonge subway interchange. Revitalized in the late 90s, the square has become Canada's busiest intersection and is often referred to as "Toronto's Times Square." There’s usually something free going on here, and the massive Eaton Centre Mall atop Dundas and Queen subway stations is a shopper’s paradise, especially in winter. The mall's Urban Eatery Food Court has something for everyone, but also try the Senato Restaurant for retro, homestyle dining charm. Further south on Yonge, it’s worth catching a tour of the Elgin & Winter Garden Theatre, the only surviving double-decker theater in the world.

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Yorkville

West on Bloor St from the Bloor/Yorkville subway interchange, is Toronto’s "Mink Mile," where the rich and famous shop and dine. Further west you’ll also find one of Toronto’s best attractions, the Royal Ontario Museum. Take your time here: the ROM is the largest natural-history museum in Canada, and you can spend an entire day wandering through its exhibits. The museum also offers walking tours that provide a wonderful insight into city life. Hungry after all that learning? The Annex Food Hall is great for quick, tasty eats in an industrial-chic setting.

Harbourfront and Corktown

Toronto’s undisputed tourism hub, lakeside Harbourfont is where you’ll find the unmissable CN Tower, mammoth Rogers Centre stadium and Ripley’s Aquarium. It’s also the boarding point for ferries to Toronto Island for summer antics and Toronto’s best skyline pics. The grand, Victorian Fairmont Royal York Hotel and Union Station transport hub are also here. Replenish at Against the Grain Urban Tavern then head east to Corktown for Toronto’s oldest architecture, including the must-visit St. Lawrence Market and the galleries, boutiques and cafes of the Distillery District.

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Entertainment District

The mainstays of Toronto’s theaters, nightclubs and a smattering of exceptional restaurants and bars are found in the Entertainment District, located on King and Adelaide Sts, west of Yonge. The Bell Lightbox cinema, proud home of the Toronto International Film Festival, is located here. And some fine places to eat reside here: a sampling of top restaurants should include at least one of Lee, Wvrst, Khao San Road, Patria or Terroni. For modern, sharp accommodations, stay at Thompson Toronto, where the rooftop pool bar is one of the city’s best kept secrets.

Queen West, Chinatown & Kensington Market

These adjacent neighborhoods appeal to an international, bohemian crowd. Heading west on Queen between University and Ossington Avenues, a concentration of eclectic merchants and shops hawk just about everything. Head north on Spadina Ave through Toronto’s Chinatown to find Mother’s Dumplings – perfect for a cheap, hearty feed. Check out the Art Gallery of Ontario, which has an extensive collection of Inuit and First Nations art. South of College St, the grungy-but-hip Kensington Market awaits. One of Toronto's most photographed neighborhoods, Kensington Market was designated a National Historic Site of Canada in 2006, and it has everything a good neighborhood needs: grocery stores, festivals, arts, restaurants and bars. Stop for a coldie at Sneaky Dee’s, the original dive bar institution.

The Annex, Koreatown & Little Italy

Heading north to Bloor St, you’ll find the Annex with its dwindling conglomeration of bookstores and cafes. It’s favored by the intellectuals and students of nearby University of Toronto, but is best known for an unexpected sight: Casa Loma, Toronto's only castle. Built between 1911-1913, the 98-room mansion was the residence of Sir Henry Mill Pellatt, who made his fortune in the electricity and rail industries but lost it to unfortunate real estate speculation (such as managing a castle), and the estate had to be auctioned off. The building is now a museum with guided tours. In this area you’ll also find Planet Traveler’s Hostel, one of Toronto’s best budget options, as well as Country Style, a Hungarian diner that serves up gargantuan breaded schnitzel – incongruous to the plethora of Korean restaurants on this strip of Bloor.

Church & Wellesley

Toronto is one of the most LGBTIQ-friendly cities in the world, with most of the excitement happening in the Church & Wellesley area, east of Yonge on Church St between College and Bloor Sts. On a sunny day, cruise from one cheery patio to the next, making friends along the way. We recommend starting at Hair of the Dog, but you might end up there all day. Partygoers won’t want to miss the enormous Pride Toronto, one of the largest gay pride festivals in the world.

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