The Coolest Neighborhoods in Toronto

Mill Street, Toronto | © Rick Harris / Flickr
Picture of Sahar Aman
Staff Writer
Updated: 18 February 2018
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Toronto’s vibrant street culture comes from the amazing number of neighborhoods in the city. Each locale has its own distinct flavor and pocket of culture waiting to be discovered. Some are steeped in history, while others are teeming with arts, style, and delicious food. Each one of these microcosms adds to the flourishing diversity for which Toronto has become known. Here are some of the city’s coolest neighborhoods!

Queen West

Vogue put Queen West on the map by crowning it the second coolest neighborhood in the world. The stretch between Bathurst and Gladstone is a concentrated collection of art galleries, truly unique shopping, design studios, bars, music venues, and hip eateries, all set against the background of historic buildings. Famous landmarks in this neighborhood include Graffiti Alley, Trinity Bellwoods Park, and artsy boutique hotels such as The Drake and Gladstone Hotel.

Queen West, Toronto, ON, Canada

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Morning light in Queen West | © marc falardeau / Flickr

Liberty Village

This former gritty industrial area is now a favorite habitat for the city’s urban professionals. Many of the historic factory buildings have been transformed into lofts or restaurants and bars, and lots of tech companies, startups, and advertising agencies have set up shop in the neighborhood. Just across the way from the BMO Field, Liberty Village becomes the spot for victory drinks after a Toronto FC win. The emerging arts scene and fresh eateries make Liberty Village a cool place for residents and visitors alike.

Liberty Village, Toronto, ON, Canada


Parkdale’s eclectic mix of architecture is home to one of Toronto’s most diverse communities. Situated between Queen West and Roncesvalles, the streets and laneways are alive with murals, tasty treats, and culture. Sample the amazing Tibetan (don’t leave without getting some momos), North African, and West Indian cuisines, peruse the vintage fashion and get your cocktail fix in one of the trendy bars.

Parkdale, Toronto, ON, Canada

Third Year in a row #MomoCrawl #FreeTibet

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Ossington Avenue

After many years of gentrification, Ossington, constructed in the 1800s as part of a military road, is now one of the most happening spots in the downtown core. The number of bars, restaurants, and boutiques that have popped up on the strip between Queen and Dundas have transformed Ossington Avenue into a hotbed for shopping, drinking, and dining. Make sure you grab a cold one at Bellwoods Brewery. Their artisan beer is known for its taste and the cool artwork on the bottle.

Ossington Avenue, Toronto, ON, Canada

Bellwoods Brewery | © Celine Kim Photography

Bellwoods Brewery | © Celine Kim Photography

The Danforth

Also known as Greektown, Danforth’s charisma and welcoming atmosphere make it one of Toronto’s most exciting neighborhoods. What began as a tiny Greek community in 1907 has now grown into the second-largest one outside of Greece and the largest in North America. The Danforth strip is where one of Toronto’s biggest foodie festivals takes place every year, Taste of the Danforth. The streets are brimming with people, and the area is chockablock with amazing places to eat, and not just Greek food! You can find tons of cuisines here.

The Danforth, Toronto, ON, Canada

King West

The westside neighborhood of King West was once at the heart of Toronto’s textile industry, and today, it’s the center of the city’s entertainment and fashion district. Although remnants of the neighborhood’s past are visible through visual landmarks such as 401 Richmond (now an art hub), King West has become one of Toronto’s most happening nightlife districts, and the place to be if you want to get a taste of Toronto’s stylish side. There’s no shortage of swanky bars and nightclubs, trendy restaurants, and chic cafés in this part of town.

King West, Toronto, ON, Canada

Toronto's Entertainment District - King West | © OTMPC

Toronto’s Entertainment District – King West | © OTMPC

The Annex

The meeting point for old-school bohemian culture and academia, the Annex borders the University of Toronto. The traditional markings of the Annex are north to Dupont Street, south to Bloor Street, west to Bathurst Street, and east to Avenue Road, although the City of Toronto also acknowledges Seaton Village and parts of Yorkville within this neighborhood. The Annex is a fusion of stunning historic domestic architecture, galleries, theatres, hippie cafés, bookshops, restaurants, and bars. Notable points of interest include a stroll along Philosophers Walk and a visit to the Royal Ontario Museum and the Royal Conservatory. During the evening, the Annex is bustling with people hitting up the countless restaurants and bars for some of Toronto’s best food and drinks.

The Annex, Toronto, ON, Canada

The Annex nightlife | © OTMPC

The Annex nightlife | © OTMPC

Kensington Market

A National Historic Site of Canada, and one of Toronto’s most eclectic neighborhoods, Kensington Market is a sought-after hangout destination for tourists and locals. Whiling away the hours among vintage clothing boutiques, vinyl shops, and hybrid eateries is the best way to make the most of your time here. A little south of Kensington Market is Toronto’s Chinatown, where you can immerse yourself in the local Asian community and visit the grocery shops bursting with produce from faraway lands.

Kensington Market, Toronto, ON, Canada

Kensington Market | © Kevin/Flickr

Kensington Market | © Kevin / Flickr

Baldwin Village

Tucked away in the Grange Park neighborhood, Baldwin Village is a mesh of Kensington Market’s cultural vibes, millennial foodie faves like the Thai ice cream rolls found at Arctic Bites, or the highly “Instagrammable” coffee treats at Light Cafe, along with some fancier dining. The area has some of the best examples of Toronto’s distinct architecture. Having grown out of Kensington Market, Baldwin Village became home to Toronto’s Jewish population, Chinese Canadians who set up shop in the neighborhood, and students. This little nook is a real gem if you feel like wandering off downtown Toronto’s beaten path for a cozy meal.

Baldwin Village, Toronto, ON, Canada

Little Italy

Little Italy may be more of a melting pot these days, but the vibe is still Italian. College Street between Euclid Avenue and Shaw Street is lined with trattorias, trendy restaurants, cafés, pool halls, and some of the best bars in Toronto. On warm summer days over the weekends, the sidewalks are buzzing with crowds queuing up for gelato, espresso, and people-watching spots on patios.

Little Italy, Toronto, ON, Canada

Little Italy signpost | © Clifton Li/Tourism Toronto

Little Italy signpost | © Clifton Li / Tourism Toronto

The Junction

Not to be confused with the Junction Triangle, this area gets its name from the fact that it is a junction of four railway lines in the area. The main intersection of the neighborhood is Dundas Street West and Keele Street. The Junction’s alluring vibrancy is due to its rich history and present-day culture, and the assortment of unique design shops, espresso bars, and restaurants found in the area. In warmer weather, the Junction BIA hosts the CONTACT Photography Festival in May and the Summer Solstice Festival in June.

The Junction, Toronto, ON, Canada


Leslieville was once dubbed the next Williamsburg by the NY Times. This eastside family-friendly, village-like neighborhood is ideal for lazy afternoons and summer evenings when all you want to do is sip on craft beers. Antique boutiques and furniture stores neighbor rustic cafés, restaurants, the city’s hottest brunch destinations, and dessert shops.

Leslieville, Toronto, ON, Canada

The Beaches

At the most eastern tip of Queen Street, by the banks of Lake Ontario, lies the Beaches. This laid-back neighborhood is a small town within a city. With a spread of parks, sandy shores, and boardwalks, there’s no shortage of things to do or quirky places to eat and drink. The locals are often seen sunning themselves, strolling or cycling the boardwalks, or working up a sweat on beach volleyball courts. The Beaches area is renowned for the annual Jazz Festival that takes place every July, attracting tens of thousands of visitors.

The Beaches, Toronto, ON, Canada

Old Town

Old Town is full of photographic gems like the Gooderham Building, also known as the Flatiron Building, and you’ll find one of Toronto’s best foodie experiences at St. Lawrence Market. The market has been around since 1803, and according to National Geographic, it’s one of the top 10 food markets in the world.

Old Town, Toronto, ON, Canada

The Gooderham Building | © Jamie Hedworth/Tourism Toronto

The Gooderham Building | © Jamie Hedworth / Tourism Toronto

Distillery District

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Courtesy The Christmas Market
Not too far away from Old Town is the pedestrian-only Distillery District. The heritage buildings and cobbled streets are home to hip cafés, design stores, and vintage shops. Behind the rustic red-brick façades, there are art galleries, delicious eats, and lots of other things to explore. The Distillery District is one of the most picturesque places to soak up some of Toronto’s charming Victorian-era vibes. Toronto’s Historic Distillery District | Courtesy of The Distillery District
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Yonge & Eglinton

Endearingly dubbed “Yonge and Eligible,” Yonge and Eglinton is a family-centered neighborhood with a burgeoning condominium scene. After the Toronto Transit Commission launched its first subway line in 1954, an influx of development transformed this one-time revolutionary district (William Lyon Mackenzie once led rebels from Montgomery’s Tavern downtown in an attempt to overthrow the government of Upper Canada) into an upscale destination for diners, shopaholics, and movie lovers.

Yonge & Eglinton, Toronto, ON, Canada

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