Simply put, Toronto is massive. With a population of almost three million, a hulking skyline, and a labyrinth of giant freeways circling the city limits, Toronto might not appear to be the most welcoming of destinations — but that couldn’t be further from the truth. Behind the facade of concrete and skyscrapers lie some of Canada’s coolest neighborhoods — places where artists dream, families grow, and local businesses prosper. And though these different districts seem to bleed into one another and may be hard to distinguish at times, each has its own quirks and camaraderie. So, without further adieu, here are the neighborhoods you should keep an eye out for while touring the Six.

Trinity-Bellwoods

Trinity-Bellwoods is a young, hip, and laidback area in the city’s west end where you’ll find Bellwoods Brewing — home to some of the best beer in town — and the eponymous park, which is without a doubt the heart and soul of the neighborhood. The perfect place to relax on a sunny day, this grassy plaza becomes swarmed with visitors as soon as the snow melts (though it does host an ice skating rink during the winter). So, if you plan on checking it out, be sure to bring a blanket and a book, and stop by the Farmer’s Market in the park’s northwest corner for some snacks before settling in. The entertainment-filled Ossington Avenue also runs through this neighborhood. Along this main drag, you’ll find coffee shops, boutique designers, pop-up art exhibits, and dive bars. Trinity-Bellwoods is an eclectic borough you won’t want to miss.

Where to stay: Delta Hotels by Marriott Toronto

Kensington Market and Chinatown

Though each neighborhood offers its own distinct character, Kensington Market and China Town’s close proximity makes them ideal for exploring back to back. Starting with the former, Kensington Market isn’t your traditional market. The area, which is a National Historic Site of Canada, is more of an open-air collection of cafés, vintage shops, grocers, butchers, and everything in between. And though these international vendors are a big draw, there are still residents in the surrounding area, making it one of the most vibrant neighborhoods in the city.

Found just south of Kensington, Toronto’s Chinatown is one of the biggest of its kind in all of North America. The area boasts an impressive assembly of food stands and souvenir stalls that showcase different aspects of Chinese culture and cuisine. It’s also the place to be during the Chinese New Year, as a ton of celebratory shows and gatherings take place here. And while you’re exploring the neighborhood, be sure to check out the Art Gallery of Ontario, which is just two blocks east from the heart of Chinatown. What more could you want?

Where to stay: Sheraton Centre Toronto Hotel

The Annex

The Annex attracts all sorts of people due to its eclectic residents, stunning architecture, and artistic history.One of the neighborhood’s big draws is the Yorkville village, an upscale area known for its picturesque Victorian homes, extensive shopping options, and fine dining drop-ins, most of which can be found along Bloors Street (also known as the “Mink Mile”). But these quarters weren’t always high-class. During the hippie movement of the 1960s and 70s, artists and dreamers found refuge here, and a few big names sprung out from the crowd, including the likes of Neil Young and Margaret Atwood. Today, these bohemian roots can still be felt, especially around the University of Toronto’s campus. The Annex continues to be a mixing pot of sorts, as families and students co-exist amid an affable and accepting environment. During your visit, spend some time poking around bookstores, exploring the Royal Ontario Museum, strolling the university grounds (one route, called the “Philosopher’s Walk,” is particularly serene), and sipping coffee in the neighborhood’s countless cafés. You’ll be surprised by how easy it is to spend a day here!

Where to stay: Toronto Marriott Bloor Yorkville Hotel

The Entertainment District

For a true taste of big-city living, you’ll want to head to the Entertainment District, located between the harborfront and Central Business District — right in the middle of all the action. This is where the city’s big names play, where festivals rave, and where the nightlife never ends. Check out the famous CN Tower, take in a Maple Leafs, Raptors, or Blues Jays game, explore Ripley’s Aquarium, or grab a pint at Steam Whistle Brewing. Additionally, take a tour down Canada’s Walk of Fame, or spend a night at the Royal Alexandra Theatre. For food and drink, some of the better-known spots include Montecito (a California-inspired establishment), Estiatorio Volos (a modern Greek restaurant), and the Rex (home to some of the best live jazz music in the city). With these suggestions in mind, it’s safe to say you’ll have no problem keeping busy in this neighborhood.

Where to stay: Delta Hotels by Marriott Toronto; Westin Harbour Castle

Old Town and the Distillery District

Wondering where Toronto keeps its history? Adventure through Old Town and the Distillery District, and you’ll see. Moving east of the Entertainment District, you’ll start to discover some of the city’s historic sites, such as Union Station, the Hockey Hall of Fame, the photogenic Gooderham Building, and the St. Lawrence Market. The market has been around (in some form or another) since the 19th century and offers a wide variety of international eateries such as Churrasco, European Delight, and Yianni’s Kitchen, all while acting as a meeting ground for locals, especially on weekends.

Back on the streets, and a bit further east, you’ll come to the Distillery District — one of Toronto’s biggest attractions. The neighborhood is pedestrian-only and complete with brick buildings from the 19th century, which have been restored and converted into everything from cafés to clothing stores. Spend the day wandering around the cobblestone streets as you uncover little bits of Toronto’s history along the way!

Want to discover more of Toronto’s charm? Be sure to check out the rest of our extensive guide from Canada’s biggest city!

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