It all started because Kevin Reilly needed something to do. He was reading about the exploits of endurance athletes and researching difficult mountain linkups that combine multiple peaks into epic hiking feats. And he decided to pursue one of his own.
Just 2 years after he and his wife moved to Colorado from Massachusetts, Reilly was in a lot of pain. In 2023, he was diagnosed with psoriatic arthritis, forcing him to take a break from his longtime career as an electrician.
He experienced intense pain if he tried to work — but it also hurt if he just sat around for too long. Reilly needed a project, so he started looking at Colorado’s biggest mountains and dreaming about something that would push him to his limits. Though he’d only hiked two of the state’s 14ers (a local moniker for mountains over 14,000 feet), Reilly felt attracted to the grandeur of the Rockies.
That’s how he came up with a linkup of La Plata Peak, Mount Massive, and Mount Elbert, three of the highest mountains in the state. With over 14,000 feet of elevation gain across nearly 31 miles, he realized his pet project could be a worthy addition to Colorado’s endless supply of outdoor challenges.
After months of intense training and planning, the 35-year-old set out on Sept. 14 and crushed the linkup in less than 24 hours. It wasn’t until later that he spoke with Fastest Known Time. It turned out that he’d “accidentally” recorded the feat sufficiently for inclusion with the record-keeping organization.
So say hello to the Cloud City Highline. It might sound daunting, but Reilly is sure of one thing: “If an asthmatic, arthritis-ridden, former smoker can do it, what’s your excuse?”
Kevin Reilly: Planning, Training for Pain and Gain

When Reilly started planning the logistics for his 14er linkup, he told GearJunkie that he had very little experience with high mountains — or endurance sports in general.
Before he began daily training that would last for many months, the longest race he’d completed was a 5K. His diagnosis in 2023 came shortly after he hiked his first 14ers: Mount Bierstadt and Mount Huron, the latter of which was his first solo ascent up a Colorado peak. But as Reilly became enamored of hiking in the mountains, he also had to confront the realities of his arthritis and its impact on his life.
“It was a really humbling thing at age 33 to ask guys to move a ladder for me,” Reilly said. “I wasn’t handling it well.”
Ultimately, Reilly said he had to take a break from his electrician job with the support of his wife, Alayna. He needed to pursue something different — find a new project. So, he began researching Colorado’s toughest mountain hikes, looking for a goal that was intense but doable.
He considered known linkups like the popular Decalibron Loop, which includes the summits of four 14ers along its 7-mile trail. But with only 3,700 feet of elevation gain, that still seemed too easy to Reilly.

‘Cloud City Highline’ FKT: 19 Hours, 53 Minutes, and 5 Seconds

