The land adjacent to the Pittwater was occupied for many thousands of years by the Kuringgai peoples, an Aboriginal Australian grouping of uncertain origin.

Amongst the Dharug there were many smaller units called clans, of which the Garigal were most prominent in the area surrounding Pittwater and the Northern Beaches.

[1][6] The first regular water transport across Pittwater was the cutter Francis which carried settlers and farm produce from Sydney between 1793 and 1800.

[7] By 1803 a fleet of privately owned coasters had begun operating between Pittwater, Cowan Creek and Berowra Waters, usually travelling in convoy to reduce the risk of piracy by escaped convicts living along the shore.

[10] The greater Sydney metropolis has extended to Palm Beach, Church Point and offshore communities in Pittwater, however its early character has been largely retained.

However, in 2016 the race was held as Pittwater to Southport (in Queensland) since the facilities at Coffs Harbour had been badly damaged by East coast storms.