Toronto is home to one of the world’s coolest streets, one of the world’s coolest neighbourhoods, one of Canada’s greatest neighbourhoods and now, apparently one of Canada’s trendiest neighbourhoods! A new ranking by Airbnb named Kensington Market one of the top 10 trendiest areas in Canada, and we’re not surprised.
The list looked at neighbourhoods all over Canada and judged “trendiness” based on the year-over-year growth in bookings made in the first quarter of 2026 versus the first quarter of 2025, specifically looking at stays booked for this summer. The top 10 neighbourhoods were the ones with the biggest “surge” in bookings this summer — and Kensington Market placed number six on the list.
The report noted that bookings in the top 10 neighbourhoods are up nearly 180 per cent year-over-year, with a typical guest in Canada spending over $300 per day — and 50 per cent of that spending happens in the neighbourhood they’re staying in.
Kensington Market is likely one of the first places we’d recommend family and friends visiting Toronto go to, so we’re not surprised it topped the list. For a tiny square streets, it’s got all the food, shopping and entertainment you would need for a full day of city adventures.
New food spots that always draw a crowd are constantly opening in the area, like this sweet and savoury cookie shop. And when one door closes in Kensington, another one pretty much always opens — like when news spread that Jumbo Empanadas would be closing and new Mexican street food spot announced its opening days later.
Same with the closure of popular local gift shop Blue Banana, which was quickly replaced with sprawling vintage store Public Butter.
The tried and true institutions can’t be missed either, though, like Wanda’s Pie in the Sky, which recently fought the threat of demolition of its dining space.
There’s also a flea market that runs down an alleyway in Kensington every weekend.
Pedestrian Sundays have even made a return to the neighbourhood after a brief pause last year, meaning the last Sunday of every month until October removes cars completely from the neighbourhood and makes strolling around even easier and safer.
And don’t forget the neighbourhood’s thriving vintage scene, home to OGs like Courage My Love and new spots like Plethora.
Kensington Market also has a rich, deep history in this city — making it an ideal place to stay for new visitors to Toronto.
For those of us who already live here, there are nine other neighbourhoods that got the “trendy” stamp of approval on this list, including another one in Ontario. Check out the list below to inspire some last minute summer travel plans.
Canada’s trendiest neighbourhoods of 2026
- Hastings-Sunrise, Vancouver, B.C.
- North End, Kelowna, B.C.
- Shaganappi, Calgary, Alta.
- McKernan, Edmonton, Alta.
- Central St. Boniface, Winnipeg, Alta.
- Kensington Market, Toronto, Ont.
- The Glebe, Ottawa, Ont.
- Le Mille Carré Doré (Golden Square Mile), Montreal, Que.
- Saint-Sauveur, Quebec City, Que.
- Downtown Halifax, Halifax, N.S.
