Canberra's John Harmer is the only person to have completed the Hawkesbury Canoe Classic a gruelling 38 times.
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The marathon has a mission: participants paddle 111km overnight to raise funds for Arrow Bone Marrow Transplant Foundation.
Mr Harmer plans to do it again this year and is among the Burley Griffin Canoe Club members entered for the Sydney race on October 24 and 25.
He has had his share of challenges on the course, experiencing "almost every weather condition available", from wind and fog to rain and thunderstorms.
Some races were bathed in moonlight; others were murky journeys in near total darkness.
His navigational skills have been tested, especially on the earlier occasions when he had to consult the map on the canoe's floor.
"We've used the GPS now, for the last few years," Mr Harmer said.
He has tackled the most recent 27 marathons with one of his sons, Steve, and they paddle on opposite sides of the boat.
"We have to call a change to keep straight," Harmer said, explaining how they set targets to stay on course.
The route is long and can be arduous, so he makes sure to do "no more, unless you have to" when it comes to distance.
Getting lost is a real possibility and there is a high risk of capsizing the small craft, which has happened three times in his history of the event.
In particular, he recalled a year when he was paddling in a single kayak and rounded a bend into a very strong headwind.
Flipping the craft means clothes and food get wet or lost and the element of night adds to the difficulty of recovering things.
There are timed checkpoints along the route and participants have land crews, but Mr Harmer said the terrain and geography of the region meant they had access to the boats in only four places.
Sharing the Canoe Classic with his son has become the highlight of the annual marathon.
Another motivation is adding to the tally of medals and acknowledgements he has collected while supporting Arrow Bone Marrow Transplant Foundation's medical research.
