Toronto’s Ossington Avenue named one of the ‘coolest’ streets in the world

Written by
Laura Hanrahan

There’s a subset of Toronto residents who can’t seem to help but talk about how cool Ossington Avenue is, and it turns out they might just be justified. Free time released its list of the 15 coolest streets in the world, and Toronto’s Ossington Avenue came out on top.

According to the ranking, Ossington is the 14th coolest street in the world, with Free time noting that West-end Avenue is home to “some of the best restaurants in town, live music most nights of the week, and the kind of parties that require leather jackets, not heels”.

The street certainly has some of the city’s most popular spots, from Bang Bang ice cream to Sweaty Betty’s dive bar. One of the street’s newest additions, Melanie Auld, has gone viral for her permanently soldered jewelry.

“The most notable stretch is between Dundas and Queen Street West: here you can parade down the street and shop for everything from carefully curated vintage to up-and-coming Canadian designer clothes,” Free time writing. “For a relaxing afternoon, head to Bellwoods Brewery or make yourself comfortable in one of the many trendy and cozy cafes and wine bars.”

But Ossington isn’t the only Canadian street to make the list. In fact, Montreal’s Wellington Street took home the top spot thanks to its upscale cocktail bars, brunches, and even its urban sandy beach. It also doesn’t hurt that the causeway becomes pedestrian-only in the summer, with a free tuk-tuk service running from one end to the other.

“When a street is booked by one of the best bars and one of the best new restaurants in town, there’s no doubting how cool it is, especially when the city in question is one of the foodie capitals of the world,” the ranking reads.

The full list of the coolest streets in the world is as follows:

  1. Wellington Street, Montreal
  2. Gertrude Street, Melbourne
  3. Great Western Road, Glasgow
  4. Yongkang Street, Taipei
  5. Vaernedamsvej, Copenhagen
  6. Karangahape Road, Auckland
  7. Tai Ping Shan Street, Hong Kong
  8. Yaowarat Street, Bangkok
  9. Oranienstraße, Berlin
  10. Hayes Street, San Francisco
  11. Avenida Amsterdam, Mexico City
  12. Kolokotroni, Athens
  13. Virgil Avenue, Los Angeles
  14. Ossington Avenue, Toronto
  15. Via Provenza, Medellin
Written by
Laura Hanrahan

Laura has covered real estate in Toronto, New York, Miami and Los Angeles. Before coming to STOREYS as an editor, she worked as an urbanized editor in Toronto for Daily Hive.

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