City2Surf (or City to Surf) is a popular road running event held annually in Sydney covering a 14-kilometre (8.7 mi) course.

The event attracts more than 80,000 entrants who start in staggered groups based on previous running times and early entry.

[6] Non-Australian athletes typically won the race from 1995 to 2007, including repeat winners Laban Chege (1999–2000), Patrick Nyangelo Lusato (2003–2005), and Dickson Marwa (2006–2007).

The most difficult part of the course is "Heartbreak Hill" at the halfway mark, a 2-kilometre-long (1.2 mi) steep ascent from Rose Bay to Vaucluse along New South Head Road.

[citation needed] Features en route include many amateur bands performing along the suburban roads, and many City2Surf participants dressed in novelty themed costumes.

[11][12][13] After the 2008 death, medical academic Michael O'Rourke noted that a runner developing arrhythmia and cardiac arrest happens most years but that the sufferer is usually revived.