What a 1,200-Mile Skateboard Journey Teaches Returning Skaters About Grit

This past summer, a skateboarder named Skyler King — a Horn Lake, Mississippi native based in Oxford, where he was president of the Oxford Skateboard Association — pushed off from the Oxford skatepark on August 1 and rolled into New York City on September 12, the city he’d been planning to move to and used the trip itself to get there. That’s nearly 1,200 miles across nine states in 43 days, with only a day and a half of rest along the way. The trip was in honor of his older brother, Justin Judkins, who died by suicide on September 3, 2024 — and who was the one who’d taught Skyler to skate in the first place, at the Latimer Lake Park skatepark a couple of miles from their childhood home.

The trip was King’s way of turning that loss into something that moved forward instead of sitting still. His fundraiser, which he called Push for Prevention, brought in almost $11,000. Donations mainly covered his own costs on the road — food, lodging, and emergencies — with whatever was left over going to the American Foundation for Suicide Prevention and the Ben Raemers Foundation, a UK-based charity working specifically to reduce the stigma around mental health inside skateboarding.

King is in his late twenties, not a returning 40-something — this isn’t his comeback story, and this isn’t a site about extreme endurance stunts either. But someone pushing a skateboard across nine states, alone, for a reason that mattered enough to him to keep going for 43 days, has more to say to this site’s readers than it might look like at first.

You don’t need his mileage to recognize his problem

The logistics of King’s trip are not relatable to most returning adult skaters. Few of us are going to push 20-plus miles a day on a board with a backpack. What is relatable is the structure underneath it: a hard goal, a body that wasn’t built for the specific demand being placed on it, and a schedule that didn’t care how tired he was on any given morning.

That’s a smaller, quieter version of what every adult comeback actually requires. You’re not skating across nine states, but if you’re coming back in your 40s or 50s you are asking a body that’s 20 or 30 years past its skating prime to relearn something it used to do without thinking, on a schedule that competes with work, family, and everything else already on your plate. The scale is different. The problem — sustained effort on a body under more strain than it’s used to — is not.

Strangers showed up, and that’s the actual story

The detail that comes up again and again in coverage of King’s trip isn’t the mileage. It’s the people. Along the route, strangers stopped to ask what he was doing, then offered food, water, a place to sleep, a ride for his gear, or just company for a stretch of road. Several told him their own stories about mental health or losing someone to suicide.

None of that was organized. It happened because a person doing something hard and visible, for a reason worth caring about, tends to pull other people toward him rather than past him.

That’s also, in miniature, what a skatepark does for adults who show up consistently. Finding other adults at your local park rarely happens because you joined something formal. It happens because you kept showing up at the same time of day, and eventually someone else who’d been doing the same thing said something. Groups like the Old Dude Skater Crew didn’t start as organizations either — they started as a couple of guys who kept showing up.

Why this matters for a comeback specifically

A long comeback — six months, a year, longer — needs more than motivation on day one. It needs a reason that still holds up on the mornings when motivation doesn’t show. King’s reason was about as concrete as they come: his brother’s memory and a destination he intended to reach, 43 days of pushing a board between him and it.

Most returning adult skaters don’t have a story that dramatic, and you don’t need one. But it’s worth being honest with yourself about what your own version of that reason is. “I want to get back in shape” rarely survives a bad week. “I’m doing this because skating is one of the only things that quiets my head down” tends to survive a lot more, because it’s a reason you can feel the absence of when you skip it.

The part worth borrowing

You’re not going to skate 1,200 miles, and you shouldn’t try to. What’s worth taking from King’s trip isn’t the scale — it’s the shape of it: a real reason, a willingness to keep going one day at a time for as long as it takes, and an openness to the people who show up along the way instead of trying to do it entirely alone.

If skating is part of how you’re processing something — stress, loss, the general weight of being 45 and trying to feel like yourself again — that’s not a lesser reason to be at the park than training for a competition. It might be the better one. It’s also, per King’s own story and the growing body of coverage connecting skateboarding to mental health support work, exactly the kind of reason that tends to keep people coming back.

Skyler King’s trip raised money, raised awareness, and by most accounts put him in touch with more strangers-turned-supporters than he expected when he pushed off from Oxford. None of that happened because the mileage was impressive. It happened because the reason underneath it was real, and he let people see it.