Before Darlinghurst’s big sandstone gaol became the prison people mean when they say “the jail,” Sydney kept its civil prisoners at the corner of George and Essex Streets in The Rocks. Governor John Hunter ordered gaols for Sydney and Parramatta in the mid-1790s. The Sydney timber gaol of about 1797 — cells plus a separate debtors’ building — burned in early 1799. It was rebuilt on the same site in sandstone: the “second” Sydney jail of this post’s title, behind high walls at George and Essex.
That sandstone gaol held men and women convicted of offences within the colony (it was not mainly a holding pen for new transportees). Public hangings took place in the grounds; the timber gallows rose high enough to be seen from outside the walls and from a hill to the west. By the 1830s the building was overcrowded, insecure and widely regarded as an eyesore on a street turning commercial. Prisoners went to the new Darlinghurst Gaol in 1841, and the George Street gaol was subsequently demolished.
The site was archaeologically investigated in a 1979 rescue excavation before hotel development; the corner is now the Four Seasons Hotel (formerly the Regent). An RAHS Green Plaque later commemorated the site of Sydney’s first gaol. Keep this post clearly about the George / Essex gaol — not Darlinghurst, not Cockatoo Island.
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