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Taylor Square is a locality in Sydney, New South Wales, Australia. Taylor Square is located beside a major road junction, where Oxford Street meets Flinders Street and Bourke Street. Taylor Square is also on the border of the suburbs of Darlinghurst and Surry Hills. The square sits above the tunnel section of the Eastern Distributor part of Metroad 1. The area formerly bound by the traffic of the three streets is popularly known as "Gilligan's Island". Construction of the Eastern Distributor also entailed the realignment of traffic flow in the area. Direct vehicle access across Oxford Street via Bourke Street is no longer possible.

The locality is a centre of the city's nightlife, especially for its gay community. It features many pubs, bars, nightclubs, restaurants, cafes and shops.

Darlinghurst Courthouse is an imposing sandstone building on Taylor Square. It was designed by architect Mortimer Lewis (1796 - 1879) in 1844, and has a Greek Revival style facade. The central block is adapted from an 1823 design in Peter Nicholson's 'The New Practical Builder' (Apperly, Irving & Reynolds, 1989).

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