Sydney Road has a history as long and tortuous as the road itself. The then unnamed route was first surveyed by William Govett who was appointed assistant surveyor in the NSW Surveyor-General’s Department in 1827. In November 1829, Govett wrote to Surveyor-General Mitchell: “Having left ‘Barrenjoey’ it is my intention to work my way back to North Head taking in as I proceed all the Country between the Main Ridge and the Sea Coast agreeable to your memorandum on my plan.”
On 13 January 1830, Govett sent Mitchell the map of his route. He had explored and surveyed “Pitt Water Range” (later Mona Vale Road) and “North Head Range” (later the route of Forest Way, the Wakehurst Parkway between Frenchs Forest and Seaforth, and Sydney Road between Seaforth and Manly). No roads were made or named although indigenous tracks may have traversed parts of these ridge-tops.
The 1890s Depression brought Sydney Road’s slow development to a halt. While a number of families moved in and out, the total number of households in Sydney Road remained almost unchanged between 1894 and 1899 (Sands’ directory of 1895-1900). Mrs McGaw’s The Castle (formerly Dalley’s Castle) was now listed in Sydney Road. Otherwise John Paxton’s Altamira on the scenic crest of Thornton’s Hill opposite what is now Crescent Street, was the first house between what is now Belgrave Street, Manly and the current Fairlight shops. Altamira’s site on the south side of Sydney Road is now occupied by a 1940s? block of flats of the same name.