The 14 km route taken by the participants commences in the city centre of Sydney and passes through the suburbs of East Sydney, Kings Cross, Rushcutters Bay, Double Bay, Rose Bay, Vaucluse, Dover Heights and Bondi Beach. The most difficult part of the course is "Heartbreak Hill" at the halfway mark, a 2 km long steep ascent from Rose Bay to Vaucluse along New South Head Road.[7]
Features en route include many amateur bands performing along the suburban roads, and many City2Surf participants dressed in novelty themed costumes.
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