Sydney's Second Jail

Sydney’s first purpose-built civil gaol stood on George Street near Essex Street in The Rocks. Governor John Hunter ordered gaols for Sydney and Parramatta in the mid-1790s; the Sydney timber gaol of about 1797 (with cells and a separate debtors’ building) was destroyed by fire 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 the corner of George and Essex Streets.

That sandstone gaol held male and female prisoners convicted of offences within the colony (it was not primarily a holding place for transportees on arrival). 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 in a street that was becoming more commercial. Prisoners were removed 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 occupied by the Four Seasons Hotel (formerly the Regent). An RAHS Green Plaque later commemorated the site of Sydney’s first gaol. Keep the post clearly about the George Street / Essex Street gaol, not Darlinghurst itself.