Australia - Dark Stories True Crime Tours

1809: Thomas Dowlan Hanged in Sydney for Burglary at Hawkesbury

Thomas Doolan, described as an old offender who had been tried several times in the colony, was convicted of forcibly breaking into the house of John Styles at Hawkesbury. He had previously saved himself from execution by turning informant against his accomplices, some of whom were hanged on his testimony.

Doolan was hanged in Sydney on 26 August 1809. Court records from the same period reveal he had also been among those who burglariously broke into the dwelling of a settler named Thomas Harley, beating the occupants and ransacking the house, though he did not live to face that additional charge.

Motorway 1 bridge over Hawkesbury River near Sydney with traffic

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Australia Burglary Execution Hawkesbury NSW Prison Robbery Sydney

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1877: Martin Cash, the Bushranger Who Cheated the Gallows, Dies at His Farm

Martin Cash, Irish-born convict and bushranger, died on 26 August 1877 at his farm cottage in Glenorchy, Tasmania, aged 68. Twice he escaped from the supposedly escape-proof Port Arthur penal colony, the second time by swimming the shark-infested waters. On Boxing Day 1842, Cash and two companions absconded from a work party and launched an eight-month bushranging spree across Van Diemen’s Land, robbing mail coaches and homesteads before his eventual recapture. His 1870 autobiography, The Adventures of Martin Cash, ghostwritten by a fellow former convict, became a bestseller. He was one of the few bushrangers of his era to die of natural causes, cheating the gallows.

Martin Cash Author: The Bushranger of Van Diemen's Land in 1843 — Martin Cash Author: The Bushranger of Van Diemen’s Land in 1843

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Australia Bushranger Convict History Death TAS

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1840: The Coorong Executions after the Maria Massacre

In June 1840, the ship Maria wrecked on Margaret Brock Reef off Cape Jaffa, South Australia. All twenty-six aboard reached shore, but the survivors later split into groups as they attempted to make their way towards Adelaide. Those travelling along the coast entered the territory of the local clan, where they were killed in a series of attacks. The remaining survivors were also pursued and subsequently killed.

Major O’Halloran, acting under orders, rounded up members of the local clan and conducted a summary field trial on the Adelaide frontier. Two men were hanged on 25 August 1840, in what colonial authorities framed as justice for the massacre, but which many historians regard as an act of punitive colonial retribution.

Major OHallorans 1840 expedition scene with mounted party

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Adelaide Australia Cape Jaffa Colonial Crime Coorong Execution Historical Crime Massacre SA Trial

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1909: Long Bay Gaol Opens on the Shores of Botany Bay

Sydney‘s Long Bay Gaol opened in 1909 on the shores of Botany Bay, and over the following century it would become one of the most storied prisons in the country. Its walls held razor gang queens Tilly Devine and Kate Leigh, escape artist Darcy Dugan, and gangsters Chow Hayes and Neddy Smith.

Long Bay also housed some of the darkest figures in modern Australian criminal history, including corrupt former detective Roger Rogerson and serial killer Ivan Milat, who died there in 2019. Russell ‘Mad Dog’ Cox staged a daring breakout from the prison’s maximum-security unit, cementing the gaol’s reputation as a place where Australia’s most dangerous and notorious converged.

Historic prison buildings at Long Bay Gaol in Australia

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Australia Corruption Escape Gang Murder NSW Organised Crime Prison Serial Killer Sydney

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