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By Brett Warren

The world’s ‘coolest’ streets for 2022 (and 2 are in Australia)

Australia has some of the most luxurious properties, best beaches, and now… some of the ‘coolest’ streets in the world.

So what makes a street particularly ‘cool’?

That’s what Time Out asked more than 20,000 people for their Time Out Index for 2022.


According to the locals in each city, it's down to a whole range of things.

It can be about food and drink establishments, museums, parks, or art galleries.

And a cool street can be a vibrant community space, a thriving business district, or just a place that oozes fabulous vibes.

Since Time Out’s inaugural street hotlist last year, the world has crept further back towards normality.

And many countries around the world still face ongoing health restrictions and rising living costs.

But now restrictions have eased, and travel has picked up to levels not seen since the pandemic began.

And there are some places in particular which are attracting the most attention.

From grand avenues and shopping strips to pedestrianised backstreets and leafy squares, these 33 streets are some of the world’s most exciting cities – each one chock-full of independent businesses, creative humans, and everything else that makes urban life brilliant.

And the best part?

Australia features on the list… twice!

Which Aussie streets made the list?

Gertrude Street in Melbourne ranked in an impressive second place on the top 33 ‘coolest’ streets list.

“Once upon a time, Gertrude Street was just a well-trodden Fitzroy thoroughfare,” the ranking reads.

“But as the rest of the suburb has steadily fallen victim to gentrification, Gertrude – beautiful, unassuming, and devoid of the rampant nightlife of its comparatively rowdy siblings – has steadily added a wealth of independent retail, drinking, and dining joints to its cultural portfolio.”

The 850-metre long street is very leafy, slow, and peaceful and is surrounded by heritage-listed buildings.


Elsewhere on the list, Enmore Road in Sydney placed at number 24 thanks to its haven of excellent restaurants, bars, pubs, and boutiques.

“The local ‘weird is welcome’ edge is very much in evidence here, with the action centred around the historic Enmore Theatre: an art deco landmark-turned-legendary culture hub with serious cred for live music and comedy gigs,” Time Out says.

“While some of the portals to the street’s old character have succumbed to shiny new fit-outs (RIP, Sly Fox Hotel) there are still remnants of Enmore Road’s rough-’n’-ready, laid-back charm and inclusive spirit.”

Which cites make the top of the list?

Top of this year’s list is Rue Wellington in Montreal, thanks to its gastronomic prowess and a vast number of thriving local businesses.

In second place was Melbourne’s Gertrude Street, which has slowly but surely added to its cultural portfolio in recent years, followed by Great Western Road in Glasgow, which boasts vintage shops, craft beer breweries, and swanky coffee shops galore.

The fourth was indie food paradise Yongkang Street in Taipei, while the fifth was Copenhagen’s Værnedamsvej, the epicentre of the hyper-cool Vesterbro neighbourhood.


Top 33 coolest streets in the world

  1. Rue Wellington, Montreal
  2. Gertrude Street, Melbourne
  3. Great Western Road, Glasgow
  4. Yongkang Street, Taipei
  5. Værnedamsvej, Copenhagen
  6. Karangahape Road, Auckland
  7. Tai Ping Shan Street, Hong Kong
  8. Yaowarat Road, BangkokFlinders Station View From Flinders Street Melbourne Australia
  9. Oranienstrasse, Berlin
  10. Hayes Street, San Francisco
  11. Avenida Ámsterdam, Mexico City
  12. Kolokotroni, Athens
  13. Virgil Avenue, Los Angeles
  14. Ossington Avenue, Toronto
  15. Via Provenza, Medellín
  16. Calle Ocho, Miami
  17. Deptford High Street, London
  18. Praça das Flores, Lisbon
  19. Oxford Street, Accra
  20. Wentworth Avenue, Chicago
  21. Cutting Room Square, Manchester
  22. Capel Street, Dublin
  23. Jumeirah Beach Road, Dubai
  24. Enmore Road, SydneySydney
  25. Kagurazaka, Tokyo
  26. Kloof Street, Cape Town
  27. Süleyman Seba Caddesi, Istanbul
  28. Calle Echegaray, Madrid
  29. MacDougal Street, New York
  30. Carrer del Comte Borrell, Barcelona
  31. Newbury Street, Boston
  32. Colaba Causeway, Mumbai
  33. Everton Road, Singapore

About Brett Warren Brett Warren is National Director of Metropole Properties and uses his two decades of property investment experience to advise clients how to grow, protect and pass on their wealth through strategic property advice.
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