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.