(MANITOU SPRINGS, Colo.) — Dawn has yet to break the horizon at the Manitou Incline when we meet Raymond “Superman” Bailey. He was preparing to start his 496th trek to the top of the incline. The chill of the late October air swirls as only the sounds of crunching dirt echo. A stream of headlamps and flashlights illuminates the 2,768 stairs.

Late last November, Bailey set a goal of reaching the summit 500 times in less than a year. On Saturday, Oct. 25, starting at 9:30 in the morning, he’ll make the journey to meet that goal.

Only 36 people since the 500 Incline Club started in the ’90s have become members. Bailey is set to become the 37th.

“I like doing hard things,” Bailey said. “I quit drinking six years ago, and the addiction doesn’t leave you, so you have to find something else to get addicted to.”

Truly, his journey to the 500 Incline club started six years ago when he opted for a life of sobriety. “I have an amazing, supportive wife named Stephanie. When I quit drinking, I went to San Francisco the day before to see Metallica and dropped almost $1,200 on alcohol that weekend. I came back and she discovered all of it and said it’s me and the boy or the drink, so I chose wisely and put the drink down.”

Shortly after, Bailey took to running. His passion for the Incline followed. His attire for each trip up sticks out: a Superman onesie, which he says he wasn’t searching for, but found at a Target a month or so into sobriety. “I wore it out on a run, and I saw people laughing and smiling, and I said, ‘We need more smiles in this world.'”

On Saturday, Bailey plans to finish his trek up and down the incline by 11:30 a.m. If you would like to attend to cheer Bailey on, keep in mind that Manitou Springs will be hosting the Emma Crawford Coffin Races that day.