The horseshoe-shaped valley that is located just east of
Sydney and stretches from William Street to the Harbour is known as
Woolloomooloo. Once a swampy hunting ground for the Gadigal people,
Woolloomooloo was not one of Sydney’s most desirable early settlements.
Although the valley was eventually drained, which left mudflats in the wake of
the swamps, the area was still largely impassable when the creek ran high. The
more disreputable members of society tended to congregate here and often
waylaid unwitting travellers.
Although the wetlands may not have initially been attractive, they were quite
fertile. The early settlers struggled to farm the new land in the unfamiliar
Australian climate, but Woolloomooloo was ideally suited to farming. Commissary
General John Palmer built a home and a farm here after being given a land grant
in 1793, and his fruit trees and tobacco crops proved extremely successful. The
valley was originally christened Wallabahmulla, but Palmer called his home by
the creek Woollamoola House, a name that eventually inspired rhymes, poetry and
By 1822, Palmer had sold his home and property to Edward Riley, who had begun
to develop a large estate in Surry Hills. Sydneysiders soon discovered the
allure of Woolloomooloo’s naturally enclosed swimming area, the Fig Tree Baths.
Governor Ralph Darling soon began to offer land grants to those of high status
and encouraged the building of homes that could meet specific standards along
the higher lands along the ridge. The lower land began to be subdivided in the
mid-19th century and was used to build smaller cottages.
Woolloomooloo enjoyed a brief period of popularity and was considered to be
quite a fashionable suburb, but by the late 19th century, its heyday was over.
As the wharf expanded, the population deteriorated. The finer houses were left
to crumble, and Woolloomooloo became overcrowded, dirty and cluttered with
brothels and pubs that serviced the sailors that came in and out. Once-pretty,
well-regarded Woolloomooloo was now left in tatters with an increasingly rough
population and a dire housing situation.
The suburb could have been left to itself, but in the mid-20th century, a new
day began to dawn for this little valley. The State Planning Authority cleared
the way for high-rises, and a section of railway was designed to travel
overhead across the Domain. There were plenty of naysayers who assumed that
Woolloomooloo could never be brought back from the edge, and the population
fled in droves. However, developers continued to buy property with plans to
redevelop it in the hopes of recreating this forgotten suburb while many others
fought to save the culturally and historically significant places. An agreement
was finally reached in 1975 that allowed land to be used for public housing,
preserved the heart of Woolloomooloo and still allowed for specific
Today, Woolloomooloo offers close access to Sydney’s CBD and top attractions,
such as Darling Harbour, Chinatown and the various markets. Woolloomooloo Wharf
has been restored and continues to be a favourite location for visitors who
seek its incredible views of the Sydney skyline. Woolloomooloo is also home to
Finger Wharf, the largest wooden structure in the world. Its dining options
include a variety of ethnic restaurants ranging from Asian to Italian, and
visitors can enjoy a quick meal before heading off to the historic Old Fitzroy
Theatre for a show.