Ossington makes exclusive list as one of the coolest streets on the planet

Arts and Entertainment guide Time Out named Toronto’s Ossington Street in the city’s west end one of the coolest in the world. Ranked at number 14 out of 33, Ossington Street grabbed the guide’s attention thanks to trendy bars, restaurants, and shops.

Ossington is home to several hot spots where, according to Time Out, where one can find live music and other assorted distractions any night of the week. Known to city-dwellers as a go-to spot for several years, Ossington recently went through a rebirth post-Covid, with new businesses opening and many old haunts welcoming more crowds than ever.

Time Out describes Ossington nightlife as “…the kind of nights out that call for leather jackets, not heels.” We couldn’t love this description more. This stretch of Ossington is definitely more thrifty than Louis (unless it’s vintage, of course) and has that urban grit we’ve all come to know and love.

The ’33 Coolest Streets in the World’ list, curated by local guides and editors, sought out the trendiest streets home to independent businesses, artists, and all those tiny details that make locals flock to a particular part of town time and again.

Specifically, the guide notes the stretch of Ossington between Dundas and Queen street where “… you can parade the street and shop for everything from carefully selected vintage to garms by rising Canadian designers.”

Ossington’s favourite cold spot, ”Bang Bang Ice Cream and Bakery” was noted in the guide’s review of Ossington as the place to grab something delicious, while fan favourite ”Sweaty Betty’s’‘ is described as a ”true dive bar experience.” If dive bar life isn’t your scene, Bellwood’s Brewery also garnered a mention as one of the top places to grab a brew.

Of course, the ever-popular permanent jewellery trend didn’t escape the eyes of Time Out reviewers through the mention of the Melanie Auld jewellery shop that will solder a bracelet around your wrist for a minimal fee (a true expression of love or friendship!).

We have to agree that Ossington is a great street to explore when searching for vintage goods or something to eat and the perfect destination for TO tourists.

As with anything great in the city, you may want to visit Ossington during the week when suburbanites are at bay or choose to mingle in the overly dressed crowds on the weekends – either way, Ossington is an easy pick for a night (or day) out.

Ossington isn’t the only Canadian city to make Time Out’s list. Montreal’s ”Rue Wellington’ snagged the top spot as the coolest city in the world, beating out Melbourne’s ”Gertrude Street” (number two) and Glasgow’s ”Great Western Road’ ‘ (number three) for the coveted position. As with Ossington, Wellington is home to several beloved restaurants and unique shops.

To see the full list of the best streets in the world according to Time Out, check out the complete article here. We’re feeling pretty fortunate to live in a city with one of the coolest streets and a short flight or drive away from the number one street.

And, for an inside look, check out musician Ron Hawkins’ fave Ossington finds here.