5 Toronto neighbourhoods that should be considered some of the coolest in the world

You've probably already heard by now, but Toronto failed to register on Time Out's 2026 round-up of the coolest neighbourhoods in the world — a fact that I take issue with, because Toronto is undoubtedly cool.

"Toronto is cool, Toronto is cool," I, like scores of fellow Toronto residents, mutter to myself, rocking back and forth in the corner of my bedroom forever and ever. 

But it actually is. While Ontario earned a nod on the list this year for downtown St. Catharines (an inclusion I enthusiastically agree with), in past years, Toronto's own Davenport Village and Ossington have both gotten their nods, too.

Rightfully so: they are both cool areas. Or, at least, areas where cool people go, but I think that Toronto, being the mosaic of micro-enclaves that it is, is home to a whole lot more "cool" neighbourhoods that deserve recognition, so I've compiled a list of my favourites.

But first, let's define my method of measuring a neighbourhood's "cool" factor. A "cool" neighbourhood is the sort of neighbourhood that you walk away from a day in with a camera roll hundreds of images heavier than it was when you woke up. From interesting architecture to scenic streets to aesthetic latte art, it's the sort of area that people want to prove they visited.

A diverse selection of restaurants, bars and cafes always helps, alongside decent retail options to keep you bopping from storefront to storefront all day, and a unique history also adds a distinct character edge that's lacking from the city's more decidedly un-cool neighbourhoods.

Leslieville

Situated on the southeastern reaches of the city, this idyllic enclave has been on the come-up for a few years now, particularly thanks to its multiplying lineup of buzzy restaurants.

Stroll along the neighbourhood's main Queen East drag, and you can tuck into lunch at Tatsuro's or Masa Deli, grab a cocktail at Bar Mini or Bar Bokeh, or score a delish dinner at staples like Corduroy Lounge or Ricky + Olivia. To say that Leslieville is a burgeoning culinary destination is an understatement: it's burgeoned.

Ricky + Olivia is just one of the restaurants that's quickly making Leslieville a destination. Photo by Fareen Karim.

Originally largely occupied by gardeners who frequented the nurseries of George Leslie (hence, Leslieville), the neighbourhood's penchant for all that's green and leafy is alive and well. In the spring and summer months, residential streets burst with life from loaded gardens and mature trees, while, just over the neighbourhood border in Riverside, the Queen Garden Centre poses as a lush neighbourhood hangout.

Little India

Speaking of culinary destinations, this eastern neighbourhood that officially goes by the name Gerrard India Bazaar serves up flavour in spades.

A historic enclave and cultural hub for South Asian immigrants since the late 1960s, the neighbourhood's history remains embedded in its businesses, from longstanding restaurants like Lahore Tikka House and Udupi Palace to grocery and clothing stores selling imported comforts.

It's not just South Asian cuisine that's found a home in Little India, though. More recently, the area has become an incubator for talented chefs to embark on bold experiments. The results, like Lake Inez, Harry's Charbroiled, Belle Isle and Puerto Bravo, speak for themselves.

Mirvish Village is eagerly upping the Annex's curb appeal. Photo by Kris Yue.

The Annex

Like it or not, young people create the current of coolness in the city, and this neighbourhood, which borders on UofT campus, is home to scores of them, so there's got to be something to it, right?

A deeply tight-knit community, the area's numerous cafes (Typist Studios, Yellow Flower, First + Last are among some of the favourites) become de facto clubhouses, regularly adding vintage pop-ups, music shows, and meet-ups for communities of all stripes and colours, nearly as often as they pull shots of third-wave espresso.

Stroll down Bathurst, and you'll be met with a handful of trendy restaurants, including Tiny Market Co. and Daisy May's, before stumbling upon the rapidly blossoming Mirvish Village development, which is home to plenty more, including Book Bar, Badiali and Blackbird Baking Co.

If sightseeing is more your scene, you're in luck. One of the city's older neighbourhoods, residential streets like Palmerston, Markham and Euclid are rife with century homes that'll excite your curb envy to no end.

At night, the area also comes to life with the help of an assortment of spots that appeal to a variety of audiences, like performances at the 918 Bathurst Centre, DJ nights at 915 Dupont or concerts at the beloved Lee's Palace.

The Junction

Situated at the intersection of two CP rail lines, this western neighbourhood boasts a history that dates back as far as the late 19th century, when the addition of rail lines, race courses and, later, vast industrial projects, began building it up as a then-independent city.

The Junction (and other communities in what was then the City of West Toronto) officially amalgamated with Toronto in 1909, but its varied history can still be seen in the post-industrial shells that now house apartments, artist studios, and an impressive suite of cafes, bars and restaurants.

Revamped industrial facades hide groovy hangouts in the Junction. Photo by Fareen Karim.

Now a hub for artists and musicians, you can always find a good time in this neighbourhood, whether at live performances at Osler Records (once an aluminum manufactory), dancing the night away at Cafeteria, or grabbing a slice at Gram's Pizza.

Brockton Village

A truly multicultural neighbourhood, the best of what makes Toronto tick can be found in this area that spans the area of Dundas West and College between roughly Dufferin and Lansdowne.

Bordering on the city's unofficial Little Portugal, the area has historically been home to a diverse array of European immigrants from, yes, Portugal, and plenty of other countries, too.

Unstuffy and laid-back, this is the neighbourhood equivalent of those meandering summer days spent with friends where you pass from one location to another, to another, to another, unwilling to go home because you're simply having too much fun hanging out.

Gather your crew and set out to Brockton Village, and you'll find good times abounding at haunts like Swan Dive, Maria's Sports Bar, Lula Lounge and the Baby G.

Take some time to explore the surroundings, popping into local independent businesses like Sixteen Eleven Studios or Souvenir, and you'll quickly learn that the area's diversity hasn't dwindled: it's only grown more vibrant.