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A satire by Patrick White.

Prior to white settlement, the area from Broken Bay to Sydney Harbour was inhabited by the Guringai people. However, by the 1840s, most had been wiped out by smallpox or driven away. Over 800 sites record the Aboriginal culture and their bond with the land, including rock engravings, axe-grinding grooves, burial sites, cave shelters, middens (sea-shell mounds) and ochre hand stencils.

Richard Rouse (1774–1852), Superintendent of Public Works and Convicts at Parramatta, once occupied this estate and was succeeded by seven generations of descendants. The 1813 Historic Houses Trust property features a convict-built Georgian residence, outbuildings and gardens. The furniture dates from the 1830s to the 1960s.

The irascible and disliked Governor Bligh threatened to curtail the privileges enjoyed by officers of the NSW “Rum Corps”, so named for their use of liquor as a form of currency. They “arrested” Bligh as retaliation in 1808, but their coup was short-lived as they were soon ordered back home to England.

From a penthouse atop the Woolloomooloo Finger Bay Wharf, the star of Master and Commander continues to enjoy water views.

Park’s two most famous novels, The Harp in the South , (1948) and its sequel Poor Man’s Orange (1949), explored life in 1930s Surry Hills, which was then one of Sydney’s poorest slums. She is also a prolific children’s author and penned the much-loved Muddle-Headed Wombat series.

A five-time premier of NSW, Parkes was a major proponent of Federation in the late 1890s (see Federation Pavilion).

Artist and writer Norman Lindsay (1879–1969), much loved for his 1918 classic children’s book The Magic Pudding and his paintings and sculptures of satyrs, nymphs and sirens, occupied this Blue Mountains property from 1912 until his death. Springwood, as it came to be known, is now a museum and gallery with an extensive collection of Lindsay’s work, including novels, watercolours and sculptures. The main house, studios and pleasure gardens are all open to the public.

Australia’s oldest Gothic Revival cathedral was designed in 1868 by Edmund Blaket, who also designed St Stephen’s (see Camperdown Cemetery). It contains many memorials to Sydney pioneers, such as the 19th-century merchant-prince Thomas Mort, a major figure in the history of Sydney’s harbour.