Jail break

From its rough origins two centuries ago, this city has undergone wrenching changes that made it what is today. Few places encapsulate the evolution from disease-ridden, convict hell-hole to prosperous, 21st-century metropolis better than Darlinghurst Jail. One of Sydney's best-preserved colonial buildings, the jail dominates the trendy inner-city district of Darlinghurst but remains a secret to most people, hidden behind thick walls.

Once a place of unimaginable hardship and misery, the prison contains underground tunnels, ghastly punishment cells, convict-era graffiti and tales of ghosts. Rapists, murderers and Aboriginal bushrangers were among the 76 people who swung from the hangman's noose there, between 1841 and 1908.

Their bodies were cut down and taken to the morgue, a handsome little building close to the main gate. A sinister skull-and-crossbones motif above the front door was recently restored with a grant from the state government. Its naive style is a faithful replica of the original, which was deliberately destroyed in the 1920s when the jail was converted to a technical college.

'It was an embarrassment for people who didn't want any reminder of the prison period, so they chipped it off,' said Deborah Beck, a drawing lecturer who has published a history of the site, Hope In Hell. The jail's origins go back to 1822, when the perimeter walls were built by convict labour.

Its radial design, with seven two-storey cell blocks built around a circular chapel, was modelled on the Eastern State Penitentiary in Philadelphia. It was meant to allow guards to easily monitor the prisoners from a single central location.

Darlinghurst Courthouse, next door, which is still in use, was completed in 1844 and is linked to the jail by an underground tunnel. That passage has been blocked off, but you can see the steps leading down to the entrance in a damp corner of the prison known as the sculpture garden. Among the most chilling remnants of the prison era are the jail's tiny punishment cells - there's one right outside Ms Beck's office. The size of a toilet cubicle, they would have been horrifyingly claustrophobic - so small that a prisoner could stand or sit but not lie down.