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Bars and pubs have thrived in the area since 1916, when ”six o’clock trading“ was introduced by the New South Wales state government. This local version of Prohibition forced all licensed venues to close at 6 pm, and sly-grog shops proliferated in the Cross as a result. During World War II, late-night clubs opened to entertain American servicemen on leave, a tradition that grew during the Vietnam War. In 1967, US Air Force veteran Bernie Houghton, who ran covert air operations for the CIA in Vietnam, opened the infamous Bourbon & Beefsteak bar-restaurant, a favourite haunt of both American GIs and the city’s criminal classes. Now known as The Bourbon, this local watering hole reopened in March 2013 after a major renovation. Some locals are lamenting the loss of its rough-as-guts decor and ambiance, while others are relieved that its bar-room brawls, sticky floors and ever-present aroma of stale beer are things of the past. Instead, patrons can enjoy live music and New Orleans-style cuisine, from jumbo shrimp to jambalaya.

The resident boho crowd may be wary about the slick renovations of local institutions, but they have welcomed recent initiatives at the Kings X Hotel with open arms. Since mid-2011, this six-storey building on the corner of William Street has hosted FBi Social, a venue run by the alternative radio station of the same name (94.5FM). Live music by up-and-coming local bands and one-off art and performance events are staged from Thursday to Saturday; on other nights of the week the hotel’s rooftop bar is a popular draw. Patrons include locals, backpackers staying in nearby hostels and music fans from across the city.

It seems unlikely that the tawdry scene along Darlinghurst Road will change any time in the near future, but the rest of the Cross is benefitting from an influx of residents who are firmly committed to retaining, promoting and building on the neighbourhood’s rich bohemian heritage. For a fascinating guide to the area’s past, follow the City of Sydney’s heritage walking tour. And for a glimpse into its future, wander north of the famous red-and-white “Enjoy Coca-Cola” billboard and into the many streets and laneways off Darlinghurst Road, where the true heartland of this fascinating neighbourhood lies.

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