The road was to follow the route of the Aboriginal foot track Maroo, which contoured between south head and Sydney.

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.

By the early 1930s New South Head Road had become a major route as it linked the wealthy suburbs on the harbour foreshore to Sydney's centre.

In the late nineteenth century a tram line was added to New South Head Road.

The line left New South Head Road in Vaucluse as it became a single track down to Watson's Bay.

Today the road serves as a major link to the city from the predominantly upper and middle class suburbs of the Woollahra municipality.

The road is serviced by a number of bus routes connecting the Sydney CBD to Vaucluse, Watsons Bay and Dover Heights.

The road also serves as the major leg of the Sydney City to Surf running event, and is famous for the steep ascent from Rose Bay to Vaucluse known as Heartbreak Hill.

[9] The route was allocated State Route 76, just after the opening of the Kings Cross Tunnel, in 1976, along New South Head Road and Hopetoun Avenue; the north-eastern end was re-aligned in 1993 to run along the complete length of New South Head Road and end in Vaucluse.