Wedged between up-market Paddington and the red light district of Kings Cross, Darlinghurst has something of the ambience of both, with its beautiful architecture and undercurrent of adrenaline. The odd mix is a result of the topography; Darlinghurst’s a mixture of hills and ridges, which in the earliest days brought rich people to the heights, and working families to the valleys.

Polar opposites

The contradictions can also be seen on Oxford Street, the road that divides Darlinghurst from Surry Hills. Today, Oxford Street is the artery of Sydney’s gay community, with Taylor Square, in the middle, its beating heart. Named for the convict Robert Taylor, who once owned the land, it’s home to a number of iconic nightclubs, including Kinselas, which used to be a funeral parlour. Yet across the road from all this debauchery is the very solid Darlinghurst Courthouse, whose sandstone edifice glowers at its neighbours.

Past the Courthouse is Forbes Street, the home of the National Art School. It boasts one of the most imposing entrances in Sydney, thanks to the two massive half towers on either side of the doors. There’s a reason it’s so secure-looking – it used to be a jail. In its time was home to some of the colony’s most notorious criminals, including the bushrangers ‘Captain Moonlite’ and Jimmy Governor.

Building began in 1822, and prisoners moved in around 1840. Sited on a hill, the jail was supposed to dominate the skyline so that Sydney-siders would look up and think about the consequences if they stepped out of line.

The thing was, life inside wasn’t all that bad, thanks to Governor Henry Keck.

Convict life

An Irishman, Keck had arrived in Sydney a few years earlier with his mistress – who was masquerading as the governess of his six children. As for his actual wife, he claimed she was dead, though he later employed her as the jail’s Matron. Keck fathered 12 children between the two women, so perhaps it wasn’t surprising that he – along with his turnkey, and a corrupt local magistrate – set out to make money from the convicts “in every possible way”.

They sent prisoners out to earn wages as servants and coachmen, and set others to work making clothes, shoes and hats. When demand was high, prisoners would work through the night. Livestock were kept on the grounds and fed with the prisoners’ rations; if the prisoners wanted to eat, they had to buy food from Keck’s shop. There was even a jail brother, which proved so popular, prostitutes had to be brought in to keep up with demand. Perhaps surprisingly, given the amenities, there were 25 escapes during Keck’s tenure. When the authorities finally investigated him, it turned out he’d got the job with forged qualifications. But he wasn’t punished for his corruption and died a wealthy man.

Jail life wasn’t all rum and prostitution, however. After noted Australian poet Henry Lawson was incarcerated for alcoholism, he wrote of his experience in the poem One Hundred and Three – which refers to his cell number – and called the place ‘Starvinghurst’ because of the terrible rations.

Used as an interment camp in World War I, it became a technical college in 1921.


But the criminals didn’t disappear when the jail closed. The building boom of the 1840s had brought large numbers of men to the area, and prostitutes followed. By the 1890s, the thriving sex trade had attracted gangs of criminals who brought bootlegging, gambling and drugs in their wake. Because heavy penalties were imposed on anybody carrying a concealed weapon, criminals carried razors rather than guns, and Darlinghurst became known as ‘Razorhurst’.

The two most notorious crime bosses of the twentieth century were women: Kate Leigh, mistress of prostitution, sly grog and cocaine, and Tilly Devine, queen of the bordellos. The two women, who kept up a famous feud, became famous for their flashy furs and diamonds.

The war years brought soldiers and their money into the mix, keeping the black market buoyant. But during 1960s, the criminals were gradually displaced by bohemians, artists and the gay community. The first gay Mardi Gras caused a riot and more than 50 people were arrested; today, the Sydney Gay and Lesbian Mardi Gras is one of Australia’s biggest festivals.

Other landmark Darlinghurst buildings include the Australian Museum – a noted natural history museum – and the Sydney Jewish Museum, which focuses on the Holocaust and on Australian Jewish history. There’s also the Darlinghurst Fire Station, a three-storey brick and stone building built in 1910.

Where to eat

Victoria Street, the main thoroughfare, has become a restaurant strip. Two Sydney institutions are here: Tropicana café, where you can get a hearty pasta meal or a breakfast fry-up, is the birthplace of the Tropfest film festival, which began as an informal film screening in the café. Across the road is Bar Coluzzi, dating from the 1950s, and credited with introducing espresso coffee to the city. Today, the shoebox café walls are crammed with photos of patrons past and present, and people sit outside on stools, small chairs and even milk crates to sip their coffee.

A few doors down is the German restaurant Una’s, best known for serving schnitzels so big, that they’re a test of manhood to eat in their entirety. On the other side of the road, the French are represented at Sel et Poivre, an eatery serving snails, brioche and bowls of coffee, among other French delights. The upscale a tavola has been making waves with its Italian cuisine; around the corner, in a converted terrace house on Liverpool Street, is Bills, created by celebrity chef Bill Granger. Best known for its breakfasts, including the world’s tastiest ricotta pancakes, this is the place for serious celebrity spotting. At night, the place to see and be seen is the Victoria Room, where you can enjoy a drink in British India surrounds.

There is also a second restaurant strip, Stanley Street, which features a range of cuisines from Japanese to European. Perhaps the best-known eatery here remains Bill & Toni’s, where the pasta and schnitzel isn’t posh – nor, for that matter, is the plastic chair-on-tile décor – but where you can get a hearty meal that won’t destroy your wallet.

The move upmarket

Part of the reason there’s so much variety on offer is that today’s Darlinghurst is because of successive waves of migration, from convicts, to mill workers, to black marketeers and prostitutes, to post-war Italians and Greeks, to the current wave of young professionals who have gentrified the houses.

How gentrified is it? Well, the mill workers who once huddled in the cottages in the ridges of Darlinghurst would have been astonished to learn that their tiny houses now fetch more than a million dollars each when they come on to the market,. The houses on the hills are now only for the extremely wealthy, and that’s assuming they haven’t been divided into flats. Even so, there are still enough writers, artists and bohemians around to ensure that, for all the new money that’s poured into the area, Darlinghurst has still got quite an edge to it.

Felicity Carter


This article first appeared in Where magazine.

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