Fifty years ago Trevor Hamilton took part in the very first City to Surf fun run, at the encouragement of a mate.
He recalls having to walk a reasonable amount of the 14km course, and finishing in about 85 minutes.
The Springwood resident, now 72, hasn't missed a City to Surf since, earning him 'legend' status.
"To me, 14km is quite do-able at a reasonable speed," Mr Hamilton said. Running helps maintain his fitness over winter when he doesn't always feel so inclined to get out in the cooler weather.
While he'd been looking forward to a big celebration for the 50th year, coronavirus has forced the popular event to be run virtually this year.
On October 18, Mr Hamilton ran 14km in the national park at Glenbrook, making sure to log his 50th run.
He never imagined he would still be doing the race 50 years later, and plans to enter the event for as long as he can.
One of the most eventful years was at around age 35, when having torn his cruciate ligament, he decided to complete the entire race on crutches, which took about three hours.
Mr Hamilton was matter of fact about the challenge.
"It was not a big ask. I've done harder things than that," he said, alluding to cross country skiing for five to six days from Kiandra to Thredbo wearing a 28kg backpack and surviving blizzards.
His quickest City to Surf time was 56 minutes when he was in his mid-30s.
A teacher for more than 40 years, Mr Hamilton was awarded a Medal of the Order of Australia for his service to the Blue Mountains community in 2018.