On Monday 6 June 2011 a commemoration, organised by the Woollahra History and Heritage Society, was held at Watsons Bay to mark the 200th anniversary of the building of the Old South Head Road.

The construction of the road to South Head commenced on 25 March 1811 and was undertaken by 21 soldiers of Lachlan Macquarie’s 73rd Regiment. The road followed the approximate route of an earlier track cleared to the look-out post (later site of the Signal Station) and was completed in ten weeks.

Initially referred to as the South Head Road, it became known as the Old South Head Road to distinguish it from the New South Head Road built along the Harbour’s edge from 1831. Part of the road, from Paddington to Bondi Junction, was gradually renamed Oxford Street from 1875. A stone obelisk marking the road’s completion stands near Robertson Park, Watsons Bay.