For the first few years of construction progress was slow and only parts of the road began to develop, as work was treacherous with the route offering a range of harsh environments such as the low lying swamplands of Rushcutters Bay, Double Bay and Rose Bay, to the steep cliff faces of Vaucluse and Watsons Bay; in addition, the bush lands surrounding the Maroo Track were reportedly infested with snakes.
 However, by 1834 efforts had increased, and the road began to take shape.
Where the road crosses Rushcutters Creek, a succession of bridges were built, starting with a timber bridge around 1834, followed by a stone bridge erected between 1837 and 1839.
Bentley's Bridge, as it came to be known, was built by convicts under supervision of Lieutenant ACD Bentley.
By the late 1830s, the road was able to cater for carts and stretched from Rushcutters Bay to Vaucluse, finally providing Sydneysiders a coastal thoroughfare along the southern banks of the harbour.
For the first few years of construction progress was slow and only parts of the road began to develop, as work was treacherous with the route offering a range of harsh environments such as the low lying swamplands of Rushcutters Bay, Double Bay and Rose Bay, to the steep cliff faces of Vaucluse and Watsons Bay; in addition, the bush lands surrounding the Maroo Track were reportedly infested with snakes.  However, by 1834 efforts had increased, and the road began to take shape. Where the road crosses Rushcutters Creek, a succession of bridges were built, starting with a timber bridge around 1834, followed by a stone bridge erected between 1837 and 1839. Bentley's Bridge, as it came to be known, was built by convicts under supervision of Lieutenant ACD Bentley. By the late 1830s, the road was able to cater for carts and stretched from Rushcutters Bay to Vaucluse, finally providing Sydneysiders a coastal thoroughfare along the southern banks of the harbour.
New South Head Road, Sydney