5 trendy Toronto neighbourhoods you'll want to explore

Like every big city, Toronto is a collection of neighbourhoods, each with its own style, vibe and scene. You might find yourself in a shopping mecca in the morning, a historic market around lunchtime, and surrounded by popular bars at night.

Here’s a look at 5 of Toronto’s major neighbourhoods and what you might expect out of each.

Old Town and the Distillery Historic District

Much of the City of Toronto can be traced back to Old Town. This collection of six neighbourhoods has seen a revitalisation as trendy shops and restaurants took over space in centuries-old buildings.

In Old Town you’ll find one of the city’s best foodie destinations: the St. Lawrence Market. The market has existed in some form since 1803, and just four years ago National Geographic named it the best in the world. Treat your senses, as you see, smell, and sample fresh produce and cheese, or browse the works of countless local artisans selling souvenirs, clothing, jewellery, and more.

Not far away, pay a visit to the Distillery Historic District, a pedestrian-only village featuring heritage buildings that now house everything a modern traveler might enjoy. New fashion can be found in restored, Victorian-era buildings; culinary inventions are hidden behind weathered red brick walls; and art galleries and performance venues host events year-round, ensuring that the old neighbourhood is full of life. 

Don’t leave Old Town without paying a visit to the Gooderham Building. Widely known as the Flatiron Building, this red-brick, narrow structure stands in stark contrast to the surrounding skyscrapers, making for a great Instagram photo. Gooderham Building. Widely known as the Flatiron Building, this red-brick, narrow structure stands in stark contrast to the surrounding skyscrapers, making for a great Instagram photo.

The Entertainment District

If you enjoy performing arts, festivals, sports, and major attractions, the Toronto Entertainment District is the aptly-named place to be.

It’s in this neighbourhood that you can see celebrities and their fans at the annual Toronto International Film Festival. It’s in this neighbourhood that you might run into Drake at a Toronto Raptors or Toronto Blue Jays game. It’s in this neighbourhood that you can spend your days at the city’s biggest attractions, from the CN Tower to the Ripley’s Aquarium of Canada, and your nights in some of Canada’s most popular clubs and bars

There is an infinite amount of ways to spend a day in the Entertainment District. If you don’t even know where to start, we’d recommend going for a stroll on Canada’s Walk of Fame, stopping at Luckee Restaurant and Bar for renowned chef Susur Lee’s modern Chinese food, and then heading to the Yuk Yuk’s Comedy Club that helped launch the careers of many Canadian comedians, from Jim Carrey to Howie Mandel.

Yorkville + the Annex

Once a hippie neighbourhood, Yorkville is now just hip, and is widely known as a fashion district. Sometimes dubbed the “Mink Mile,” Bloor Street is lined with designer boutiques where you can shop brands like Tiffany, Chanel, and Hermès. The posh stores are straddled by equally posh dining, all of which make Yorkville a great place to mingle with high society.

It might be surprising, then, to discover that the University of Toronto campus sits right along its border. Since students aren’t known to shop luxury boutiques and eat haute cuisine, most spend their time in the adjacent Annex neighbourhood.

The Annex’s popularity and style are largely driven by the university students that inhabit it. Droves of coffee shops, theatres, bookstores, galleries, restaurants, and bars are filled day and night with a young, trendy clientele. The neighbourhood really comes alive in the summer when patios open up and you can enjoy the weather with your meal.

Chinatown + Kensington Market + AGO District

Kensington Market is an incredible street market that really reflects the wide diversity at the core of Toronto. Caribbean, Latin American, European, and Vietnamese immigrants have all found a home in the area over time, each leaving their stamp in a variety of ways. This diversity comes to life in the superb mixture of restaurants and cafes, the vintage clothing shops and lively market stalls.

Just south of Kensington market is Toronto’s Chinatown neighbourhood, a fantastic place to immerse yourself in the local Asian community. Dine on authentic Chinese, Japanese, Thai, and Vietnamese cuisine before browsing the markets for international produce, unique products, and souvenirs. If you really want to experience the best of Chinatown, visit during the Chinese New Year when the community comes together to celebrate and dancing dragons roam the streets.

While in the neighbourhood, make sure to stop at the Art Gallery of Ontario, home to a remarkable 90,000 works. This is one of the biggest and best art museums in North America, and is where you’ll find the largest collection of Canadian art in the world as well as works from legendary artists like Rubens, Goya, Picasso, and Rembrandt.

Queen West + King West + Liberty Village

Queen West is where you’ll find the city’s coolest kids. It has great shopping, tons of art and design studios, a variety of live music venues, and amazing food, all of it set against a backdrop of historic buildings. Walking through the streets you’ll stumble upon hidden galleries, drum circles in Trinity Bellwoods Park, ‘art hotels’ like The Drake, and “Graffiti Alley,” the self-explanatory street art hub that might just be the perfect background for your next profile photo. Is it any wonder Vogue named West Queen West one of the coolest neighbourhoods in the world?

Fashionistas tend to congregate, which is why nearby King West is also home to some of the best shopping in the city. Housed in what was once the centre of Toronto’s textile industry, the former industrial buildings of King West are now inhabited by clothing outlets and retailers.

Another former industrial area, Liberty Village is now the popular place to live for Toronto’s urban professionals. You can live, eat, and drink, all in old, converted buildings that used to house factories. The industrial spirit lives on through the neighbourhoods latest residents: tech startups, digital agencies, and advertising firms.