Skyler King poses in downtown Gate City, Virginia. Photograph by Sally Ammerman.
For Skyler King, the idea of skateboarding from Mississippi to New York began with a few different pieces of his life coming together.
King had already planned to move to New York City after graduating from college. He had spent time there before, and also been offered a place to stay. But in December 2025, another idea began to take shape. Instead of simply making the move, King would skate there.
The idea was inspired in part by his friend Demarcus James, whom King met in California. James had previously skateboarded from San Francisco to New York, and watching that journey left an impression on King.
King had also seen others undertake long-distance journeys to call attention to causes that mattered to them. One friend had ridden a bicycle from Oxford to South America and had also completed a 1,000-mile walk.
Those examples gave King a way to combine his own upcoming move with something larger.
The journey is also deeply personal. In 2024, he lost his brother, Justin Judkins, to suicide. At the time, King was in the middle of transferring from Northwest Community College to Ole Miss, making an already difficult transition even harder.
Now, as he travels north on a skateboard, King is raising awareness about mental health and suicide prevention while honoring his brother.
The trip began in Oxford, where King had spent several years involved in the local skateboarding community. He had operated the Oxford Skateboarding Association, a nonprofit organization focused on keeping skateboarding active in the community.
The association has worked on efforts to revitalize and expand the local skate park, as well as hosting competitions, skate clinics, and other programs.
“I was kind of carrying the weight of that,” King said of his work with the organization.
So, his journey has become more than a trip from one city to another, but a continuation of the work he has already been doing in Oxford, only now on a much larger scale.
Life on Four Wheels
King first picked up a skateboard when he was six years old. Growing up in Horn Lake, he had a skate park just a couple of miles from home, and his older brother was an avid skateboarder.
By the time King was ten, he was spending more time skating and began to take it seriously.
For his cross-country trip, King is riding a Creature 8.75-inch, a fish-shaped board with a square tail and rounded, pointed nose. He had been riding the same board for about six months before setting out, putting it through considerable preparation for the journey.
As part of his training, King skated the Tanglefoot Trail, which stretches about 43 miles from Houston to New Albany. On one occasion, he and a friend skated the trail roundtrip.
By August 28, King had already been on the road for nearly a month, and there had not yet been a typical day.
Every morning he wakes up in a new town, encounters new people, and adjusts his plans according to the road, the weather, and whatever else happens. Sometimes those adjustments are minor, but other times plans are completely changed.
During one stretch in Virginia, King was caught on a back road by a severe thunderstorm. With night approaching and no obvious place to take shelter, he stopped near a farm. A woman noticed him and offered him the use of her barn.
The storm quickly intensified, and King took her up on the offer.
Later, the woman’s elderly mother came to check on the unexpected visitor. After learning what King was doing, the family eventually offered him a place to spend the night.
King left early the next morning, but the encounter stayed with him. That kind of hospitality has become one of the defining parts of his journey.
People have stopped along the road to check on him. Others have offered food, rides, or lodging. In small towns, residents sometimes see him skate by and simply want to know what he is doing.
The physical demands are considerable, too.
Early on in the trip, in Tennessee, he took a hard fall and suffered a road rash on his arm that took weeks to heal. There were other times of difficult weather, including one day when he covered about 30 miles during storms.
His route changed as a result, sending him through towns he had not originally planned to visit. Even so, King has come to see those unexpected detours as part of the experience.
Meeting People along the Way
Perhaps the most meaningful part of King’s journey has not been the miles themselves, but the people he has encountered along the way.
Again and again, conversations with strangers have turned into something deeper.
King said many of the people he meets have their own experiences with depression, mental health struggles, or the loss of someone close. Sometimes a brief roadside conversation becomes an emotional exchange with folks he had never met.
“There’s so many specific moments I could bring up,” King said.
One encounter came after King had skated through a small town during more bad weather. Near the end of the day, he passed a man who was fishing and casually asked if he had caught anything, then continued down the road.
A short while later, the man caught up with him in his truck. He had recognized King from earlier and was amazed at how far he had traveled.
When King explained that he was skating across the country to raise awareness for mental health and suicide prevention in honor of his brother, the man shared his own history with mental health and suicide attempts. He also told King that he was now a local preacher.
For King, encounters like that have reinforced the reason he decided to make the trip.
One family he met at a campground turned out to live in Phoenixville, Pennsylvania, which was along his route. They told him to contact them when he gets close so they can provide him with a meal and a place to stay.
Another woman in Virginia has been checking in with him regularly, and that type of support has helped make an otherwise lonely journey feel less isolated.
“It’s pretty lonely out on the road,” King said. “But I’ve got a big group text and people online are checking in, making me feel a lot better.”
As King moves north, he has also changed his approach to the trip. Originally, he had a target date for reaching New York, but after making it more than halfway, he decided to slow down. He realized that moving too quickly meant missing out on some people and places in the process.
There is still a destination in mind. King hopes to reach the legendary skate spot Brooklyn Banks, although he is not sure exactly what his arrival will look like. He is not particularly interested in turning the finish into a spectacle.
And while New York was supposed to be the end of this journey, it may not be the end of the story. King said his mother has already suggested that he keep going. Perhaps even skating through all fifty states.
Whether that happens remains to be seen. For now, the important thing is the road ahead, the skateboard beneath his feet, and the people he continues to meet.
Back in Oxford, the skateboarding community he helped build remains part of that journey. At the local skate park, a bench made from skateboards donated by local skaters stands in memory of King’s brother. Lafayette High School students built the bench before donating it to the park, where anyone can sit, watch the skaters, or simply spend some time. It is a fitting reminder of where King’s journey began.
From Oxford to New York, he is carrying that community with him, one mile, one friendly conversation, and one push of the skateboard at a time.
September is National Suicide Prevention Awareness Month, a dedicated time to share resources, promote mental health awareness, and break the stigma surrounding suicide.
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