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Darlinghurst Road runs from the court house to the Alamein Fountain. “The Wall”, a sandstone wall running beside the gaol, is a nocturnal beat for male prostitutes. The pleasant Green Park is thought to be named after a former hangman at the gaol, Alexander “The Strangler” Green. Beyond the park is a colourful strip of terrace houses, hotels and cafés that ends at William Street. In the 1920s and 30s the area beyond William Street had some bohemian charm, but since WWII it has been Australia’s most notorious red-light district.

This dandelion-shaped fountain in the Fitzroy Gardens is especially pleasant when illuminated at night. Though many consider it overrated, it is still probably Sydney’s most popularly known public artwork. Designed by Robert Woodward in 1961, it commemorates the participation of Australian soldiers in the Battle of El Alamein in Egypt during WWII, which precipitated Germany’s defeat in North Africa.

Alexander Macleay, Colonial Secretary of NSW from 1825 to 1837, had architect John Verge design this residence for his large family in 1839. Macleay was also a distinguished botanist and the first president of the Australian Museum. This Greek Revival residence is said to contain the finest example of a Colonial interior anywhere in Australia. Macleay’s family subdivided the original 23 ha (56 acres) of land following his death. In 1941 the house was further divided into 15 apartments. The NSW government purchased the property in the 1960s and the Historic Houses Trust undertook major restoration. It finally re-opened as a museum in 1977.

Rushcutters Bay, now the mooring of choice for some of Sydney’s finest yachts and the home of the Cruising Yacht Club, was the site of one of the settlers’ first run-ins with the local Eora people, on 30 May 1788. The Eora speared two convicts, who were collecting rushes for roof thatching after having stolen a fishing canoe. Today, this pleasant park contains tennis courts, a quaint picket-fenced cricket ground and stadium, lovely Moreton Bay fig trees and a pleasant kiosk and café. The park is much loved by both locals and their poodles.

Following WWII almost 30,000 Holocaust survivors migrated to Australia, many of them settling in Sydney. This museum explores Australian Jewish history and presents recordings of survivors, audio-visual displays and photographs. The ground floor deals with Jewish life following white settlement, and the upper levels focus on the Holocaust, whose survivors act as guides.

These stone stairs link Woolloomooloo Bay with Potts Point and The Cross. Near the bottom of the stairs on Cowper Wharf Road is Harry’s Café de Wheels, a pie cart that’s been a Sydney late-night institution for over 50 years. Its walls are festooned with photos of famous patrons, mostly politicians and pop stars, tucking into meat pies. Nearby is the Woolloomooloo Finger Wharf (see Harbourside Mansions & Penthouses), which houses upmarket bars and restaurants.

“Villa conditions” were actually established in the 1830s to ensure that the hillside overlooking Woolloomooloo Bay attracted the “right sort”. All new houses had to face Government House, cost a fortune, and be approved by the governor of the day. John Verge designed both Tusculum and Rockwall. The Australian Institute of Architects now occupies the former, which has a great bookshop specializing in architectural titles. Rock-wall is a private residence originally built for engineer John Busby, whose bore delivered Sydney’s first permanent fresh water supply.