If you've ever waited for a bus at Taylor Square, you've stood right next to two of the oldest public buildings in Sydney. Behind the big sandstone columns of the Darlinghurst Courthouse on Oxford Street, and running down Forbes Street and along Darlinghurst Road, are the high walls of the old Darlinghurst Gaol. These days art students wander in and out with sketchbooks and a coffee, but for more than seventy years this was Sydney's main prison, and around 76 people were hanged here. The courthouse next door has been hearing criminal trials since 1842, and it still does.
I wrote a short piece on the Darlinghurst Gaol back in 2015 and another on the Darlinghurst Courthouse in 2021. This time I wanted the full story: why the gaol was built, how it was built (very slowly), who ended up inside, and some of the famous trials heard next door.
Out With the Old: The George Street Gaol
Before Darlinghurst, Sydney's gaol stood on the corner of George and Essex Streets in The Rocks (I wrote about it in Sydney's Second Jail). By the 1830s it was falling apart and hopelessly overcrowded. When the High Sheriff, Thomas Macquoid, reported on it in 1835, he found 110 men sharing one dormitory 32 feet by 22 feet. In another room, 27 feet by 22 feet, there were 40 women and 10 children. From 1826 the overflow had been put aboard an old prison hulk, the Phoenix.
A new gaol had been on the cards for years. In 1820 Commissioner John Thomas Bigge, sent out from London to report on Macquarie's colony, directed that one be built on a conspicuous site. Governor Brisbane reserved three and a half acres on the high ground above Woolloomooloo, on the edge of town, where a prison could be seen from all over Sydney. That was the point.
Greenway's Walls and the Woolloomooloo Stockade
Francis Greenway pegged out the site in 1821, and convict gangs started on the walls in 1822. The Register of the National Estate says S. L. Harris saw them finished in 1823–24. Then the money ran out, and for about twelve years there was little more than a big walled yard on the hill.
It didn't sit empty, though. The enclosure was used to hold convict gangs working on the roads and other public works, and it became known as the Woolloomooloo Stockade. John Ramsland, writing for the Dictionary of Sydney, describes it as "an elevated area of windswept bush and sand dune", a detention camp for prisoners who couldn't be squeezed into George Street or onto the Phoenix. The name hung around. In 1844 people were still calling the new prison "Woolloomooloo Gaol".
Stone From the Ridge
The sandstone didn't have to travel far. The State Heritage Register says convicts quarried it nearby, around the corner of William and Forbes Streets, and hauled it up the hill, where other gangs dressed the blocks by hand. Some historians say it came from Thomas West's Barcom Glen estate, which was also close by. Ramsland reckons 30,000 tons of stone went into the walls alone.
Each convict cut his own sign into the blocks he'd quarried so his quota could be counted. Once he'd cut his quota, he could be assigned out to a settler. About eighty different marks turn up again and again, and you can still spot plenty of them today, especially high on the Darlinghurst Road wall. The walls are up to eight metres high in places, with watchtowers along them.
Hyde Park, Museum, Darlinghurst Gaol, Sydney Grammar School, Burdekin's & Lyons' Terraces, 1842, by John Rae. The new gaol stands on the skyline up on the Darlinghurst ridge.
Credit: John Rae, State Library of New South Wales, public domain, via Wikimedia Commons.
Mortimer Lewis, George Barney and the Radial Plan
Things got moving again under Governor Bourke. A Select Committee reported on the plans in August 1836, and building started up again that year. The new design came from Mortimer Lewis, who had become Colonial Architect in 1835, and Captain George Barney of the Royal Engineers. According to the Dictionary of Sydney, Barney "radically altered" Lewis's plans. Lewis also suggested building the new courthouse right beside the gaol to save money, and that's why the two still stand side by side.
They came up with a radial plan, following the ideas of the Society for the Improvement of Prison Discipline in London and Jeremy Bentham's "panopticon". The cell blocks were set around a central point so they could all be watched from one place, and Ramsland says the model was the Eastern State Penitentiary in Philadelphia. Seven two-storey wings were planned around a central round building. The government soon changed the plans to fit more people in. Cells meant for one were redesigned for three, and some blocks got six-person cells. The full radial layout was never finished.
In 1836 a chain gang of about eighty convicts lived inside the walls while they built, sleeping at night in portable wooden boxes. Free tradesmen worked there too.
At the centre is the round building, two storeys high with a glassed watchtower on top. Its ground floor was in place by 1847 and was used for a while as a kitchen. It was finally finished as the chapel in 1872, with fittings that could be reversed for Catholic or Protestant services and iron bridges linking it to three of the cell blocks. Henry Lawson even mentions its gilded weathercock in one of his poems.
The March From George Street, 7 June 1841
On 7 June 1841, nearly twenty years after the walls went up, the inmates of the George Street gaol were marched through town and up the hill while crowds jeered. Ramsland says the heavily ironed bushranger Patrick "Paddy" Curran was at the head. Behind him came about fifty women prisoners, veiled and dressed in black. The women went on wearing that drab outfit until 1909.
The place still wasn't finished. Only the porter's lodge, the Governor's Residence and A Wing were complete, D Wing was nearly done, and B and C had only just been started. Building went on for decades. B Wing came in 1849 and C Wing in 1861. In 1864–66 the walls were pushed out to Burton Street, and then a Y-shaped E Wing was added. A new gatehouse and a male hospital followed in 1885, and by 1891 the gaol had sewerage and electricity. The Dictionary of Sydney reckons it took about fifty years to finish.
Darlinghurst Gaol, painted by one of its own prisoners, Henry Louis Bertrand, in 1891. That's the round chapel in the middle, with men cutting stone in the yard.
Credit: Henry Louis Bertrand, State Library of New South Wales, public domain, via Wikimedia Commons.
Life Inside the Walls
Life here was meant to be hard. Under the "separate" system borrowed from Philadelphia, some prisoners spent up to nine months in solitary. From 1867 prisoners were sorted into classes A, B and C, and class C covered drunks, harmless lunatics and debtors. By the 1870s Darlinghurst was a "labour gaol". Inmates made mats, shoes and mattresses, and did tin-smithing, blacksmithing, bookbinding and stonemasonry.
It was always crowded. At the end of 1877 there were 596 prisoners (453 men and 143 women), and 8,016 people had come through the gates that year, but there were separate cells for only 348. By 1885 a gaol built for 650 was holding more than 700.
The women were held in D Wing, which is now the Cell Block Theatre. Many of them came back again and again. Margaret Greenwood, in the photo below, came out as a convict in 1833 and was convicted twelve times over the years. Her picture went into the gaol book in 1875. NSW gaols began photographing prisoners in 1871, and those description books are haunting to look through. From 1909 women went to the new State Reformatory for Women at Long Bay instead.
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Margaret Greenwood, "an Imperial convict", in the Darlinghurst Gaol photographic description book, 1875.
Credit: NSW State Archives (State Records NSW, NRS 2138), CC BY 2.0, via Wikimedia Commons.
Owing money could land you in here too, because the gaol had its own debtors' section. When Henry James O'Farrell was charged with shooting Prince Alfred in 1868, his preliminary hearing was held in the debtors' prison. Café NAS now sits in the old debtors' quarters.
Henry Lawson knew the place all too well. Between 1905 and 1909 he was locked up there several times for drunkenness and for not paying maintenance to his wife, and he nicknamed it "Starvinghurst". The National Art School says he wrote "One Hundred and Three" (his prison number) while he was in the debtors' section. It tells you more about the place than any official report:
They shut a man in the four-by-eight, with a six-inch slit for air,
Twenty-three hours of the twenty-four, to brood on his virtues there.
And on the food: "Bread and water and hominy, and a scrag of meat and a spud".
The Gallows
The National Art School counts 76 people hanged at Darlinghurst between 1841 and 1907. The Dictionary of Sydney says 79. (For Sydney's earlier gallows, see my posts on the first execution in the colony and the first public gallows at the Barley Mow.)
At first hangings were public and took place right outside the main gate on Forbes Street. The first man hanged at the new gaol was John Knatchbull, a former Royal Navy captain who'd been transported for theft. In January 1844 he killed a shopkeeper, Ellen Jamieson, with a tomahawk. His barrister, Robert Lowe, argued "moral insanity", which the heritage listing calls a first for a British court. It didn't work. Knatchbull was hanged on 13 February 1844, and Caroline Overington writes that more than 10,000 people came to watch.
"Woolloomooloo Gaol": the crowd outside the gate for the execution of John Knatchbull, 13 February 1844.
Credit: Artist unknown, State Library of New South Wales, public domain, via Wikimedia Commons.
The hangman then was Alexander Green, who lived in a hut outside the eastern wall. The last public hanging outside the gaol was on 21 September 1852, when Francis Thomas Green was executed. After that executions moved out of public view, for a time on a gallows over the gate. Then in 1869 a purpose-built gallows went into E Wing. From 1876 to 1904 the hangman was Robert "Nosey Bob" Howard, who hanged 61 men and one woman.
'The Gallows' from the Keep Yard: The Scaffold at Darlinghurst, drawn by a confinee (a prisoner) in the 1800s.
Credit: Unknown prisoner-artist, State Library of New South Wales, public domain, via Wikimedia Commons.
Henry James O'Farrell was hanged on 21 April 1868. Andrew George Scott, the bushranger "Captain Moonlite", went to the gallows on 20 January 1880 alongside Thomas Rogan, one of his gang. The gang had been caught after the siege at Wantabadgery near Wagga Wagga in November 1879, in which Constable Edward Webb-Bowen was fatally shot. On 7 January 1887 four young men were hanged together over the Mount Rennie rape case. The National Art School also records at least four Aboriginal men executed here: Mogo Gar in 1850, John McGrath in 1875, Jimmy Governor in 1901 and Thomas Moore in 1903. The last hanging at Darlinghurst was in October 1907.
The gaol's record sheet for A. G. Scott, "alias Captn Moonlight", photographed on 26 November 1879. The sheet records his sentence: death, executed 20 January 1880.
Credit: NSW State Archives (State Records NSW), CC BY 2.0, via Wikimedia Commons.
The two best-remembered hangings, Louisa Collins in 1889 and Jimmy Governor in 1901, came after trials in the courthouse next door. I'll come back to both below.
Some Famous Faces Behind the Walls
The gaol's guest list is a fair slice of colonial Sydney. J. F. Archibald and John Haynes, the founders of The Bulletin, did time here. So did Sir George Dibbs, later Premier three times, who was locked up in 1880 for slander. It didn't hurt his political career one bit. Henry Louis Bertrand, convicted over the 1865 murder of Henry Kinder, spent most of his 28-year sentence here and painted the watercolour above. The National Art School's list also includes the woman bushranger Jessie Hickman and Kate Leigh, later the sly grog queen of Surry Hills in the "Razorhurst" years. Her old rival Tilly Devine didn't arrive in Sydney until 1920, after the gaol had closed.
Closing Time, and the War Years
By 1912 there were only 323 prisoners left. The new State Penitentiary at Long Bay was proclaimed on 1 June 1914, and within about six weeks every prisoner was gone. Then war broke out, and Defence took the site over as the Darlinghurst Detention Barracks. From 1914 to 1920 German, Russian and Irish nationals were held there. The army stripped out lead and timber and left bullet marks, and many people expected the place would simply be knocked down.
From Gaol to Art School
Luckily it wasn't. In 1921 Sydney Technical College took over the site as East Sydney Technical College. The idea came from Thomas Mutch, the Minister for Public Instruction, along with James Nangle. The art department moved in in 1922, and by 1924 all of the state's technical art courses had been brought together there.
From 1926 the college offered a five-year Diploma in Art under Samuel Rowe and the sculptor Rayner Hoff, and Hoff's students helped him with the sculptures for the Anzac Memorial in Hyde Park. "East Sydney Tech" turned out artists like Margaret Olley, who graduated in 1945, John Olsen, Cressida Campbell and Fiona Hall.
From the air, about 1930. The radial plan and the round chapel are easy to spot, and the courthouse sits at the front with its curved driveway.
Credit: Mitchell Library, State Library of New South Wales (as reproduced in a history of St Vincent's Hospital), public domain, via Wikimedia Commons.
In 1955 Katharine Hepburn, who was touring Australia with Robert Helpmann, announced the Cell Block Theatre project for the old women's wing. She said how fitting it was that a member of the second oldest profession should open a building that had housed women of the oldest profession. The theatre opened in 1957. The National Art School went its own way from TAFE in 1996, became fully independent in 2009, and in 2022 marked a century on the site and two centuries since the walls went up.
The Courthouse on the Hill
When Governor Bourke arrived in 1831, prisoners were still being marched through town to the court in King Street, and he wanted a court beside the new gaol. Ambrose Hallen drew some Grecian plans that went nowhere, and then Mortimer Lewis took over. Convict gangs laid the foundations from 1835, and the building went up from 1836, mostly by private contractors. The Quarter Sessions were sitting there by 1 February 1842, and it was finished in 1844.
It was the first purpose-built courthouse in New South Wales, and for about sixty years it was the template for courthouses across the colony. The Greek Revival portico has fluted Doric columns and a pediment with the royal coat of arms. It's said the fluting stops short of the ground so passing traffic couldn't chip it.
Before it was finished it was used as a church, and in 1840 it hosted the St Patrick's Ball for 300 to 400 guests. Cows grazed among the columns until a fence went up in 1849. James Barnet, the Colonial Architect, added the court pavilions on either side in 1884–88. In 1901 the front columns were rebuilt to match his wings.
Gaol and Court House, Darlinghurst, 1872. You can see the Doric portico, cabs waiting out the front and one of the gaol's watchtowers peeping over the top.
Credit: Charles Percy Pickering, NSW Government Printing Office, State Library of New South Wales, public domain, via Wikimedia Commons.
The High Court of Australia sat here from 1903, got its own building on the site in 1923, and didn't move to Canberra until 1980. In 1954 the Royal Commission on Espionage, set up after Vladimir Petrov's defection, sat here, and Dr H. V. Evatt appeared before it. When the Quarter Sessions were abolished in 1973, the District Court took over. Today there are seven courtrooms, and it's one of only two NSW courthouses with a court keeper still living on site. In the old courtrooms you'll find graffiti carved into the timber by people waiting in the dock. (For more on the street out the front, see Oxford Street – Darlinghurst – 1788 Onwards.)
The Tunnel
You'll often hear that a tunnel ran from the gaol to the court, and this time the legend is true. The heritage listing records 434 feet of tunnelling between the two by 1846, built so prisoners could be taken to court without ever seeing the street. Lawson mentions it: "I've seen the remand-yard men go out, by the subway out of the yard". At Jimmy Governor's trial in 1900, the Sydney Morning Herald described him mounting "the staircase leading into the dock". The tunnel's entrance is still in the National Art School's sculpture garden, but it's blocked off now.
Famous Trials at Darlinghurst
For most of its life the courthouse was home to the Central Criminal Court. These are a few of the big trials I've been able to pin down to Darlinghurst.
Louisa Collins, 1888. Louisa Collins of Botany had been married twice, and both husbands, Charles Andrews and Michael Collins, died of arsenic poisoning. She was tried four times in 1888. The first three juries couldn't agree, and in December, before Chief Justice Sir Frederick Darley, she was found guilty of murdering Michael Collins. Women couldn't sit on juries in those days, so 48 men decided her fate across the four trials. Overington says Louisa walked to court through the tunnel. The Governor, Lord Carington, refused to step in. She was hanged on 8 January 1889 by Nosey Bob Howard and his new assistant, and it went badly. The lever jammed, and the pin under the trapdoor had to be knocked out with a mallet. She was the only woman hanged at Darlinghurst and the last woman hanged in New South Wales.
Louisa Collins, photographed in Darlinghurst Gaol on 28 July 1888. She was hanged there on 8 January 1889.
Credit: Museums of History NSW – State Archives Collection, public domain, via Wikimedia Commons.
Jimmy Governor, 1900. In July 1900 Jimmy Governor, a Wiradjuri man, and Jacky Underwood killed members of the Mawbey family and their schoolteacher at Breelong near Gilgandra. Jimmy was declared an outlaw, and the manhunt went on for months. The Herald reported that his trial for the murder of the teacher, Helen Josephine Kerz, opened "at the old court, Darlinghurst" before Mr Justice Owen on 22 November 1900, "punctually as 10 o'clock struck from the neighbouring belfry". His barrister argued that an outlaw couldn't also be tried, but the judge brushed that aside. Jimmy was found guilty and hanged at Darlinghurst on 18 January 1901, aged about 26.
Shirley Beiger, 1954. In August 1954 a young model, Shirley Beiger, shot her former boyfriend Arthur Griffith dead in King Street. On 23 November an all-male jury at the Central Criminal Court, sitting before Justice McClemens, acquitted her. About 150 people in court cheered, and someone in the crowd outside shouted "Good on you, Shirl". In 2025 a play about the case, A Model Murder, was staged in the Darlinghurst Courthouse for Sydney Festival.
Stephen Bradley, 1961. In 1960 eight-year-old Graeme Thorne was kidnapped and murdered just weeks after his family won the first Opera House lottery. Stephen Bradley's trial opened at the Central Criminal Court at Darlinghurst on 20 March 1961 and ran for eight days. It's remembered for its forensic evidence: hairs from the Bradleys' pomeranian, cypress seeds and pink mortar all linked him to the crime. Justice Clancy sentenced him to life.
Bruce Burrell, 2006. The big cases still come here. In June 2006 a Darlinghurst jury found Bruce Burrell guilty of kidnapping and murdering Kerry Whelan.
Heritage
The gaol went onto the Register of the National Estate in 1978 and the NSW State Heritage Register in 2021, which calls it "the oldest surviving early gaol complex in Australia". The courthouse has been on the State Heritage Register since 1999. Around the corner on Forbes and Burton Streets is the old Lunatic Reception House, another part of the same story.
Visiting Today
The National Art School is at 156 Forbes Street, and there's another entrance on Burton Street. The NAS Gallery is free and normally open Monday to Saturday, 11 am to 5 pm. In early October 2026 it was showing Margaret Olley: Australian Intimiste, a nice fit since Olley studied here. The gaol and campus tours are unavailable at the moment, so keep an eye on the NAS website. The Open Day and the Grad Shows are good chances to look around, and Café NAS is open to visitors.
Even when the gates are shut, you can walk the outside of the walls along Forbes Street, Burton Street and Darlinghurst Road and look up for those convict marks.
Darlinghurst Courthouse is still a working court, hearing criminal trials. Hearings are generally open to the public, so you can sit quietly in the public gallery. Dress sensibly, switch your phone off and do what the sheriff's officers tell you. You go in from Oxford Street, and access for people with limited mobility is restricted, so check ahead.
One last tip: the Justice & Police Museum isn't here. It's in the old Water Police Court on the corner of Phillip and Albert Streets, near Circular Quay, and it makes a good partner to a walk around Darlinghurst.
Sources
- Dictionary of Sydney, "Darlinghurst Gaol" – dictionaryofsydney.org
- Dictionary of Sydney, "Darlinghurst Courthouse" – dictionaryofsydney.org
- John Ramsland, "Prisons to 1920", Dictionary of Sydney, 2011 – dictionaryofsydney.org
- Dictionary of Sydney, "Darlinghurst" – dictionaryofsydney.org
- NSW State Heritage Register, "National Art School Group, Former Darlinghurst Gaol, Former East Sydney Technical College" (SHR 02048) – apps.environment.nsw.gov.au
- NSW State Heritage Inventory, "Darlinghurst Courthouse and Residence" – apps.environment.nsw.gov.au
- Register of the National Estate, Darlinghurst Gaol (place 2198) – environment.gov.au
- National Art School, "History" – nas.edu.au
- National Art School, "Campus" and "Visit" – nas.edu.au
- NSW Government, "National Art School (old Darlinghurst Gaol)" – nsw.gov.au
- Supreme Court of NSW, "Darlinghurst Courthouse" – supremecourt.nsw.gov.au
- Museums of History NSW, "Convict case study: John Knatchbull" – mhnsw.au
- Caroline Overington, "Where Louisa died: a tour of Darlinghurst Gaol", 2014 – carolineoverington.com
- Mark Tedeschi, Forbes Flyer No. 11, Forbes Society, 2006 – forbessociety.org.au
- Sydney Morning Herald, "The Breelong Tragedy: Trial of the Aboriginal Jimmy Governor", 23 November 1900 (Trove) – trove.nla.gov.au
- Sydney Morning Herald, 24 November 1954, Shirley Beiger verdict (Trove) – trove.nla.gov.au
- Limelight, "A chequered past", 20 December 2024 – limelight-arts.com.au
- Sydney Morning Herald, "National Art School given heritage protection", 11 February 2021 – smh.com.au
- Henry Lawson, "One Hundred and Three" (1908), Wikisource – en.wikisource.org
- Wikipedia, "Darlinghurst Gaol", "Darlinghurst Courthouse", "Louisa Collins", "Jimmy Governor", "Andrew George Scott" and "List of people legally executed in New South Wales" (cross-checks) – en.wikipedia.org
- Wikimedia Commons, Category: Darlinghurst Gaol (images) – commons.wikimedia.org
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