In 1977, members of the NSW Outward Bound Ex-Students Association organised a canoe race along the river they had paddled during their course. Apart from the challenge, the 111 km race was going to help the community by raising money for medical research. That first race attracted 250 paddlers and raised $8,500. Now the race attracts more than 500 paddlers and raises annually more than $250,000.

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Over the years records have been set and broken time and again. The fastest time outright stands at 7 hours, 11 minutes and 7 seconds, set in 1985 by Garry Byrne, Grant Hughes, Cameron Tunbridge and Brett Worth in a K4. John Harmer, one of the original 250 starters in 1977, paddled every race up to 2023 and retired after notching up 44 Classics.   Richard Barnes continues to paddle every year and in 2025 completed his 42nd Classic.  Greg Thompson in 2025 paddled his 41st at the age of 70.  A rare group of 39 paddlers have completed 20 or more. 

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The race was originally run overnight to take advantage of the calmer weather conditions and the lighter traffic on the river. It also allowed the slower paddlers to make those last painful strokes in daylight. What the organisers did not realise when they made this decision was that the beauty and magic of paddling in moonlight would far outweigh any of their practical reasons for running the event overnight.

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The race is held each year on a weekend near the end of October or early November, as close to the full moon as possible.  The weather at this time of year is generally more stable, with reasonably long daylight hours. Hundreds of volunteers work hard throughout the night to help maintain the excellent safety record that has been achieved by the Hawkesbury Canoe Classic.

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