Where to Stay: A Guide to the Coolest Neighborhoods in Downtown Toronto

Toronto is a walker’s city. Both the size and diversity of the place make it an ideal place to walk in. Within five minutes, you can find yourself transported from one era to the next and from one nation to another, and you’ll feel a shift in the energy in the air. Sadly, you will (probably) only stay in one place, and finding that perfect base camp is key for a walking city like Toronto. Here’s a guide to the city’s coolest neighborhoods, to help you find the right place to stay in Downtown Toronto.

Nowhere in the city quite compares to the cheerful bustle of Kensington Market on a summer’s day. With bars, coffee shops, restaurants, organic grocery stores, bookstores, vintage clothing stores and all manner of other little oddities, the market is as eclectic as the people who live there. The neighborhood is varied, but the music is constant. Each restaurant produces a smell from a different corner of the world, fusing flavors that have never been put together before. The pace and the energy are frenetic.

All this activity makes the market one of the louder spots to stay, so it’s a neighborhood for those looking to extend their exploration of the city into the early hours.

The Danforth is Greektown in Toronto. Although it started as a quiet community for Greek immigrants in 1907, it has since become one long strip of restaurants and bars. There are plenty of things to do during the week, but it transforms into a hub of nightlife on Fridays and Saturdays. The neighborhood is home to The Danforth Music Hall, known by everyone simply as ‘The Danforth.’ It hosts an array of household names, and its schedule is worth checking out even if you’re only in town for a few days.

Located 45 minutes (by transit) away from the city centre, staying here requires a little more planning if you want to see all the city has to offer.

Just 20 years ago the Distillery District was nothing more than a bunch of historic Victorian-era buildings, but a group of developers saw it for what it could be and set about turning it into a space for creatives, artists and entrepreneurs. What they created was exactly that. It is now one of Toronto’s most picturesque spots, with galleries and exhibits punctuating the streets. The district feels like a mix between a European patio district and the hip vibe of New York City’s SoHo.

During the day the Distillery District is a hive of activity, but come the evening it’s a lovely, quiet spot for dinner and drinks.

Old Town is the home of Toronto’s most iconic building and its most famous market: the Flatiron Building and St Lawrence Market. The historic market, established in 1803, draws crowds from across the city, with National Geographic positioning it as one of the top ten food markets in the world.

As a place to stay, Old Town is located centrally enough that all of the city is accessible to you. It also has a lot of office space, meaning that during the week it offers great opportunities for people watching.

The smallest neighborhood on this list is a small section of Ossington Avenue that runs north to south between Queen Street and Dundas Street. It is the ultimate trendy spot in Toronto’s West End. It is a foodie’s dream, a bar crawl haven and a browser’s paradise. It’s perpetually busy, but it also has the beautiful Trinity Bellwoods park right next door.

Staying on Ossington itself isn’t really a possibility, because of the real estate values there. But staying nearby gives you the best chance of sampling the Toronto West End way of life.

Trendy Toronto meets age-old scholarship in The Annex. Housing the University of Toronto, the Royal Ontario Museum and the Royal Conservatory, The Annex is the place to stay for those who want to dive into the history of Toronto. It is also an area with quiet roads and green spaces, alongside its array of cafés, restaurants and bars. The mix is a microcosm of how the seemingly conflicting forces of old and new have met and bonded in Toronto.

This is a superb location for strolling into the city’s core, while not having to navigate its busiest areas on your way home after a day of exploring.

The Beaches is the sort of neighborhood that makes you forget you’re in a city at all. The area is filled with everything you could possibly need, from entertainment to amenities, and essentially exists as a town in its own right. Located in the East End of the city, locals list volleyball, sunbathing and swimming as typical weekend activities, highlighting that it is possible to live the life of a beach bum on the edges of one of North America’s most populous cities.

The Beaches, with its easterly location, is a quiet spot to stay. It’s the ideal place if you need to find some renewal and rejuvenation on your trip.

If The Beaches is a town within the city, ‘Roncy’ is a village. Roncesvalles Avenue itself is one small strip lined with charming coffee shops, used bookstores and quaint restaurants and bars. Located in Toronto’s West End, a stone’s throw from the glorious High Park, it’s a family-friendly, effortlessly charming neighborhood. Despite how much Roncesvalles has to offer, it’s somewhat removed from the hustle and bustle of city life and so never feels too crowded.

Transit into the city is easy, as is access to lakeside cycle lanes, meaning you can enjoy some peace and quiet while not giving up on seeing the more lively areas of Toronto.

Queen West is the epicenter of Toronto cool. It has been voted the second-coolest neighborhood in the world, and most certainly lives up to the hype. With places to drink, dance, eat and shop, the neighborhood has everything a great city day out should offer. What’s so interesting about this neighborhood is feeling it evolve as you walk along it. If you start off at Spadina Avenue and walk west until Lansdowne, you’ll see how each intersection has its own personality, from mainstream to hipster, and from globally recognized names to chic local spots.

Queen West never fully shuts down. If you want to be at the center of the action, it’s a great neighborhood to stay in.

The next major street up from Queen West is Dundas West, which is the edgier, less polished sibling of the two. It’s a regular night-out spot for locals, with bars galore that range from tiny watering holes to underground dance parties. During the day it offers more coffee shops than you could ever visit, making it a great place to start a day of exploring.

This is another neighbourhood for those looking to enjoy Toronto’s nightlife or those who aren’t too concerned about nighttime noise.

The most colorful spot on the list goes to the historic home of Toronto’s LGBTQ community. Adorned at all times with art, culture and rainbow flags, the Village hosts Toronto’s Pride Festival every year and is a living, breathing hub of entertainment. During the day it’s a regular city spot with typical Toronto hustle and bustle. But when the street lights come on, the music and laughter follow and the free-spirited fun begins.

The Village is located in the middle of the city, offering you opportunities to experience Downtown Toronto and access to all major transit networks.

Cabbagetown is one of the few neighborhoods in Toronto that has really kept the essence of its spirit as the world around it has changed. Most of the stores and restaurants are mom and pop stores, giving the whole area a quiet, community feel. Nothing proves the point more than the working farm you can find in the middle of Cabbagetown’s mix of Victorian homes and global cuisine.

It’s located in Toronto’s East End, so both the Beaches and Downtown Toronto are a short stroll away.

This is an updated version of a story originally created by Sahar Aman.