The traditional Aboriginal owners of much of the Woollahra district were the Cadigal clan, while the harbour area around Watsons Bay and South Head was inhabited by the Birrabirragal clan. Both the Cadigal and Birrabirrigal clans belonged to the coastal Dharug language group.
The devastating impact of European settlement in 1788, felt particularly in the effects of introduced diseases such as smallpox, resulted in the eventual disappearance of the local Aboriginal population. While there is limited information on the lives of the Cadigal and Birrabirragal at Woollahra some of their heritage is preserved in the form of rock art, shell middens and the Sydney language. Go to Aboriginal heritage for more information.
The first European settlement in Woollahra occurred two years after the arrival of the First Fleet when a flagstaff was erected at South Head (near the site of the Signal Station) in 1790 to serve as a landmark for ships arriving at the Heads.
During the first 40 years of European settlement, the land at Woollahra was broken up and acquired by members of the colony by grant and/or purchase. The largest of the estates was the Point Piper Estate (the sole property of Daniel Cooper by 1847) which covered 1,130 acres of land in Woollahra, parts of Edgecliff, Double Bay, Point Piper, Bellevue Hill and Rose Bay.
The Woollahra district became a local government area, then known as a municipality, in 1860. In 1968, the Woollahra Municipality was enlarged with the addition of the northern half of the suburb of Paddington. Vaucluse and Watsons Bay broke away from Woollahra in 1895 to form the Vaucluse Municipality but were reunited with Woollahra in 1948.
The name Woollahra may have its origins in the Aboriginal word/s variously recorded in the 18th and 19th centuries as 'Woo-la-ra', 'Willarra' and 'Wallara'. In 1788 the First Fleet officer Daniel Southwell translated the Aboriginal word 'Woo-la-ra' as meaning 'The Look-out'. Surveyor James Larmer in 1832 reported the Aboriginal name for Point Piper as 'Willarra', also recorded as 'Wallara' by Surveyor General Sir Thomas Livingstone Mitchell ('Aboriginal placenames: naming and renaming the Australian landscape', ed. by Hercus & Koch, ANU Press, 2009).
In 1856 Daniel Cooper chose the name Woollahra for his planned mansion at Point Piper. Woollahra was adopted as the name for the newly formed Municipality of Woollahra in 1860.
Woollahra largely developed as a residential locality. In the 19th century a few local industries were established, such as a foundry and brewery in Woollahra, and distillery and tannery in Paddington; but it was Paddington that produced the biggest concentration of industries and factories during the 20th century. With the gentrification of Paddington and West Woollahra in the 1960s, most of these industries had vanished by the end of the century. Dairying and market gardens were the predominant agriculture in Woollahra, the last market gardens disappearing from Rose Bay by the 1930s. Fishing was popular, particularly around the village of Watsons Bay. Land releases and improvements in transport shaped the development of the individual suburbs and the resulting appearance of Woollahra throughout the 19th and early 20th centuries.
Woollahra's cultural heritage has been enriched by the influx of people from many different cultural backgrounds. Some of the influential immigrants to Woollahra have been the Chinese market gardeners, who began leasing land in Double Bay gully and Rose Bay in the 1880s; the Portuguese whalers who settled at Watsons Bay in the 19th century, building a church and becoming a part of the village life, and the many Europeans who migrated after World War II and helped change the face of commercial centres such as Double Bay.