Where to Stay: a Guide to the Coolest Neighborhoods 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 together before. The pace and energy are frenetic. All of this activity makes the neighborhood one of the louder spots to stay, so it’s best for those looking to extend their exploration of the city into the early hours.

Toronto has a vibrant Greektown, known as the Danforth. 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 nightlife hub on Fridays and Saturdays. The neighborhood is home to the Danforth Music Hall, which hosts big-name acts, and its schedule is worth checking out, even if you’re only in town for a few days. It’s 45 minutes (by transit) from the city center, so staying here requires a little more planning if you want to see all the city has to offer.

In 2001, the Distillery District was nothing more than a bunch of Victorian-era buildings, but a group of developers set about turning it into a space for creatives, artists and entrepreneurs. What they created is now one of the most picturesque spots in Toronto, with galleries and exhibits punctuating the streets. The district feels like a mix between a European patio district and New York City’s SoHo, complete with a hip vibe. The Distillery District is a hive of activity during the day, but in the evening, it’s a quiet spot for dinner and drinks.

Old Town is home to the most famous building and market in the city: the Gooderham Building, also known as the Flatiron Building, and St Lawrence Market. The market, established in 1803, draws crowds from across the city, with National Geographic positioning it as one of the top 10 food markets in the world. As a place to stay, Old Town is fairly central, making it easy to access any part of the city. It also has plenty of office space, offering great people-watching opportunities during the week.

The smallest neighborhood on this list is a small section of Ossington Avenue that runs north to south between Queen Street West and Dundas Street. It’s the ultimate trendy spot in Toronto’s West End. Not only is it a foodie’s dream and bar-crawl heaven but also a browser’s paradise. The area is perpetually busy and has the beautiful Trinity Bellwoods Park next door. Staying on Ossington Ave itself isn’t 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 of Music, this neighborhood is the place to stay for those who want to dive into the city’s history. It’s also an area with quiet roads and green spaces alongside cafes, restaurants and bars – a microcosm of how the seemingly conflicting forces of old and new have met and bonded in Toronto. The Annex has a superb location for strolling into the city’s core while not having to navigate the busiest areas on your way home.

The Beaches is the sort of neighborhood that makes you forget you’re in a city at all. It has everything you need, from entertainment to amenities, and essentially exists as a town in its own right. Sitting within the East End, the area offers volleyball, sunbathing and swimming as typical weekend activities, highlighting that it’s possible to live the life of a beach bum on the edges of one of the most populous cities in North America. The Beaches is a quiet spot to stay, ideal 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. In Toronto’s West End, close to the glorious High Park, it’s a family-friendly, charming neighborhood. Despite how much Roncesvalles has to offer, it’s somewhat removed from the hustle and bustle of city life and never feels too crowded. Transit into the city is easy, as is access to lakeside cycle lanes, meaning you can enjoy some peace while not giving up on seeing the more lively areas of Toronto.

West Queen West is the epicenter of Toronto cool. Vogue called it the second-coolest neighborhood in the world in 2014, and it most certainly lives up to the hype. With places to drink, dance, eat and shop, the neighborhood has everything to make your day out a great one. What’s so interesting about this area is feeling it evolve as you walk through. If you start at Bathurst Street and walk west until Lansdowne Avenue, you’ll see how each intersection has a unique character, from mainstream to hipster, and is home to both globally recognized names and chic local spots. The area never fully shuts down, so if you want to be at the center of the action, it’s a great neighborhood in which to stay.

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 ranging 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. It’s another neighborhood for those looking to enjoy Toronto’s nightlife or those who aren’t too concerned about night-time 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 Pride Toronto every year and is a living, breathing hub of entertainment. During the day, it’s a regular, bustling city spot. However, when the street lights come on, the music and laughter follow. The Village sits in the middle of the city, offering you opportunities to experience Downtown Toronto and access all major transit networks.

Cabbagetown has retained its spirit. Most of the stores and restaurants are of the mom-and-pop variety, giving the 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 sits in the East End, so both The Beaches and Downtown Toronto are a short stroll away.