East Sydney Historical WALKing tour
Be guided by a qualified historian and archaeologist on a walking tour along East Sydney (Darlinghurst) Sydney’s most infamous historical neighbourhood. This former centre of sex, vice and murder is hidden amongst the narrow lanes, convict-built cottages and in the shadow of the old Sydney prison.
About the East Sydney Historical Walking Tour
Approximately 2 Hours
The ultimate historical walking tour of Sydney for those who want to avoid the tourist traps, explore back streets and see where the locals eat, drink and party.
Fashionable Today
East Sydney (Darlinghurst) is one of Australia’s oldest and most notorious inner-city suburbs. Most people know it for Oxford Street, the Sydney LGBT Mardi Gras and the bars and nightclubs, but beyond that, it is shrouded in mystery.
A Deadly Past
For much of its history, Darlinghurst was synonymous with sex, drugs and murder. Known as Razorhurst in the roaring 1920s, it was the centre of the violent razor gang wars between the crime queens Tilly Devine and Kate Leigh. For over 100 years, the alleys and laneways teemed with prostitutes, dope dealers, and thugs.
There were once more than 50 pubs in East Sydney. One you will see, the East Village, was one of the most dangerous places in the world between 1900 and 1950. The pub where 1930s crime queen, Tilly Devine, Australia’s most dangerous woman shot the man she would later marry; one of the only pubs in Sydney where African American servicemen could drink during WW2; and the only pub ever in Sydney to completely ban women (ladies are more than welcome today).
LGBT History
Hear the fascinating history of the LGBT community of East Sydney dating as far back as the 1870s. See where the first Mardi Gras happened in 1978.
Enjoy a gentle walk from Hyde Park to Taylor Square and see the most beautiful little streets and lanes lined with old shady trees (flowering jacarandas from September to November), convict-built cottages, elegant rows of terraces and grand hilltop mansions from the Victorian age.
You will discover the hippest cafes, cocktail bars, restaurants and pubs that you will definitely want to return to.
Why choose this East Sydney Walking Tour?
Some of the Unique EAST SYDNEY locations you will explore
Hyde Park
Better known as the location of the iconic Sydney Opera House, was once the location of a colonial military fort.
Darlinghurst Prison
Part of the Sydney Domain, the gardens are full of beautiful plants, unique animals, cool history and strange mysteries.
Taylor Square & Oxford Street
Famous for its long tongue-twisting name, it is one of Sydney’s oldest and mysterious hidden neighbourhoods.
Frequently asked questions
Sydney Harbour Walking Tour Gallery
Clients Reviews
These guys have all done one of our Sydney walking tours.
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Explore the old laneways of Surry Hills and hear the stories of the gangsters and tough cops who battled for control of what was once Sydney’s most infamous neighbourhood. See the home of Australia’s prohibition-era crime queen, explore trendy Crown Street and finish at a classic Aussie pub that has operated since 1879.
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east Sydney Historical Walking Tour
Starting in Hyde Park, you will explore the winding narrow laneways of historic East Sydney. Today this area is very trendy and pretty. However, it was once the centre of Sydney’s red-light district; the battleground of the female crime lords that ruled Sydney’s prohibition era; and a battleground for US Servicemen during WW2.
Walking. 2 hours.
You won’t find this in Lonely Planet.
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