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Journey Walks

Gangsters, Girls & Grog in Old Surry Hills

64 Foveaux St
Surry Hills NSW 2010
Australia
Meeting outside El Loco at Excelsior
When
  • Sunday 9 November 2025 from 2:30pm to 5pm
Cost

Adult: $58

DISCOVER THE DARK AND DANGEROUS HISTORY OF SURRY HILLS:

Once an underworld teeming with gangsters, gambling, sly grog, prostitutes & drug lords.

THE GORY STORY

Known in the 1920s and 1930s as the ‘Chicago of the South’ —  Sydney’s Eastern Suburbs were once famous for vicious gang rivalries; terraced slum houses; midnight robberies; destitute sex workers; razor wielding thugs; cocaine addicts and illegal sly-grog shops. From the labyrinth of laneways littered across Surry Hills and Darlinghurst, the criminal empires of an emerging underworld began to make their mark in response to a series of local laws that almost seemed made to be broken.

To make matters more unusual, the most notorious of these criminal empires were ruled by two rival mob bosses with a difference – these bosses were women.

Hailed as Queens of Vice: Tilly Devine and Kate Leigh had crawled their way up from obscure origins over the bodies (sometimes literally) of men to become the most powerful women in Sydney. As they each slashed for supremacy of the Sydney underworld, they recruited every type of crook in town to protect their interests and began transforming everyday dwellings into dens of debauchery.

During these roaring inter-war years, Surry Hills and its surrounds became riddled with stories of murder and mystery, and at the same time grew to be one of the most multi-cultural and interesting suburbs in Australia.

Now, a century later, we are fortunate that so many of the historic houses, pubs and hang-outs of old Surry Hills still remain. On this true crime and architecture tour: we’ll dig beneath the trendiness of Surry’s contemporary surface to reveal the Gangsters, Girls and Grog that lurk below.

HIGHLIGHTS

  • Join a local crime historian on a professionally guided exploration of the lesser known laneways, historic structures and secrets of Surry Hills.

  • Rewind the clock to reveal a criminal empire viciously fought over by Australia’s legendary female mob bosses Tilly Devine and Kate Leigh.

  • Meet the colourful collection of working girls, gangsters, drug-dealers, hit-men, cops and robbers who called this place home.

  • Enjoy the chic surroundings and charming terrace houses once labelled as the worst slums in Sydney as we explore the fashionable neighbourhood that exists today.

Contact event organiser

Journey Walks

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