There are easier ways to get from Oxford, to New York City. You could get in a car and be there in about 17 hours. You could catch a flight out of Memphis and be looking at the Manhattan skyline a few hours later.
But for Ole Miss graduate Skyler King, who recently took a postgraduate job in New York City, he decided to skateboard there.
On August 1, King rolled away from the Oxford Skatepark with New York City somewhere more than 1,100 miles in front of him. Equipped with a skateboard, camping gear and whatever he could carry. But a reason much bigger than simply seeing if he could do it.
King calls the journey Push for Prevention. He hopes to reach New York by September 3. That date isn’t random as September 3 will mark two years since King’s older brother, Justin Judkins, died by suicide. And Justin was the person who helped put Skyler on a skateboard in the first place.
That’s what makes this journey different. This isn’t really a story about traveling 1,100 miles on a skateboard. It’s a story about two brothers.
And the thing they shared.
To understand why King chose a skateboard for this journey, you have to go back long before August 1.
Growing up in Horn Lake, Justin Judkins was a skateboarder himself. According to his obituary, Justin spent his teenage years skating and eventually passed that love of skateboarding down to his younger brother. Skyler would go on to travel throughout the South skating with friends and eventually turn what started as something between brothers into a major part of his life.
Justin didn’t leave skateboarding behind when he got older, either. He shared it with his own son, Blaine. The two would go to parks together to fish, ride bikes and skateboard. Even after Justin’s death, skateboarding remained part of the family’s connection to him. Instead of asking for flowers, his family requested that memorial donations be made to the Oxford Skateboarding Association.
So when Skyler decided to honor his brother, there probably wasn’t a more fitting vehicle than four wheels and a piece of wood.
It would be easy to see the headline and picture someone deciding on a whim to skateboard halfway across the country. That’s not Skyler King. King has been part of the skateboarding scene for years, and his résumé stretches well beyond Oxford.
The Boardr, which tracks skateboarding competitions around the world, lists King as an Oxford-based sponsored skater with support from Satori Wheels, Olympia Bearings, Dickies and New Balance flow. His competition history includes the USA Skateboarding National Championships, Vans Park Series, Tampa Am, Phoenix Am and events throughout the country.
In 2019, King reached the men’s park semifinals at the USA Skateboarding National Championships, finishing 19th in a field that included some of the best park skaters in the country. In 2024 he won the Advanced Bowl division of The Boardr Series event in Tupelo.
At Red Bull Terminal Takeover, an annual skateboarding event that transforms the abandoned former terminal at Louis Armstrong New Orleans International Airport into a massive indoor skatepark. During the 2023 event, King took on one of the old terminal’s escalator handrails, grinding down the rollercoaster-style rail in one of the event’s more memorable tricks. The run even caught the attention of Skateboarding.com, which featured it in its coverage of Terminal Takeover.
King returned to Terminal Takeover in 2024 and took home the Maui Jim Best Trick Award. That’s a pretty long way from somebody cruising around the Oxford Square on a board.
King has also helped build the skateboarding community around him. The Oxford Skateboarding Association was incorporated in Mississippi in June 2022. The organization’s mission includes improving Oxford’s skateboarding facilities, mentoring younger skateboarders, organizing events and giving Oxford’s skating community a voice.
Years before Push for Prevention, King was one of the subjects of an Ole Miss documentary called Skater Boys. Filmmaker Elise-Joelle Denoulet originally began documenting King’s friend Austin Beard before realizing how closely the two men’s stories mirrored one another. The documentary’s description says both came from complicated home situations and found something in skateboarding that went well beyond tricks and competition.
It became, in the filmmaker’s words, a refuge and gateway. A place that gave them friendship and helped shape who they became. That context makes what King is doing now hit a little differently.
For some people, a skateboard is something you grow out of. For King, it became part of how he found his community. And now he’s using it to talk about something people still struggle to talk about at all.
King recently graduated from Ole Miss and was preparing to relocate to New York. Most people would have packed a U-Haul. King decided to make the move mean something.
He announced Push for Prevention with the goal of traveling from Oxford to New York almost entirely under his own power, skateboarding whenever the road allows and walking when conditions make riding impossible. His expected distance has been reported between roughly 1,100 and 1,200 miles.
He left Oxford on August 1. The goal is to arrive in New York by September 3. That gives him just over a month to cross a huge section of the eastern United States. Anyone who has spent even a few hours on a skateboard knows what repeated pushing does to your legs. Now add Mississippi and Tennessee summer heat, hills, rough pavement, traffic, rain, carrying gear and figuring out where you’re sleeping every night.
Then wake up the next morning and do it again.
And again.
And again.
For more than a thousand miles.
King’s plan is about as stripped down as the idea itself. He has said he intends to use public campgrounds whenever possible and only turn to hotels when weather, safety or the lack of a camping option requires it.
Money raised through Push for Prevention is being used for the basics needed to complete the trip: food, water, campsites, occasional lodging, replacement skate shoes, skateboard equipment, emergency expenses and documentation of the journey.
Anybody who has skated seriously knows the equipment part is real. Shoes get destroyed. Wheels wear down. Bearings take punishment. Decks break. Now imagine doing it while trying to cover the distance between northern Mississippi and New York City.
King has also encouraged people along the route to help in ways that don’t involve money: sharing the fundraiser, offering local information, providing a meal or helping him find a safe place to stay. Whatever money remains after the expenses of the trip is expected to benefit the American Foundation for Suicide Prevention and The Ben Raemers Foundation.
The second organization makes the skateboarding connection especially important. The Ben Raemers Foundation was created in memory of British professional skateboarder Ben Raemers and works to change the way mental health is discussed within skateboarding.
For King, the mission and the sport aren’t two separate things. They are tied together. Of everything surrounding Push for Prevention, September 3 might be the hardest part to get past. Justin Judkins died on the morning of September 3, 2024, at the age of 30. His obituary paints a picture much fuller than a single sentence about how he died.
He loved motorcycles. He tinkered with things. He quoted movies. He rode BMX and inline skates in addition to skateboarding. He was a father who took his son to the park and built him a motorized bicycle so they could ride together. And he was the older brother who showed Skyler how to skateboard.
Two years later, that little piece of their relationship is carrying Skyler toward New York. There is something incredibly simple about the symbolism.
Push. Coast. Push again.
Every mile requires another decision to keep moving forward.
King has said one of his goals is to make people more comfortable talking about mental health, checking on friends, asking for help and seeking therapy when they need it. You don’t need to know anything about skateboarding to understand that message.
Mississippi produces plenty of sports stories. Most of them happen under Friday night lights, inside SEC stadiums or on baseball diamonds. But this one is happening on back roads and stretches of pavement somewhere between Oxford and New York.
There won’t be 60,000 people waiting when Skyler King rolls into another small town. There won’t be a scoreboard. There won’t be a trophy waiting for him at the end. There may be mornings when he’s tired, nights when the weather doesn’t cooperate and stretches of pavement where New York still feels impossibly far away.
But somewhere along that route is September 3. And if everything goes according to plan, King will eventually put his skateboard down one more time and push into New York City two years to the day after losing the brother who taught him to skate.
That’s why I don’t think the mileage is really the biggest part of this story. Skyler King isn’t skateboarding 1,100 miles because he wants people to see how far he can go on a board. He’s using the thing his brother gave him to make sure people remember why he’s going at all. Every push is for Justin.
And somewhere between Oxford and New York, maybe somebody sees Skyler roll past, hears his story and decides to check on somebody they haven’t talked to in a while.
Maybe somebody struggling realizes it’s okay to say something.
If that happens even once, those 1,100 miles become about a lot more than skateboarding.
Follow Skyler’s Journey
You can keep up with his progress, see updates from the road and follow the final miles of the journey on Instagram at @skyylord.
With more than 1,100 miles between Oxford and New York, every day of the trip brings a different stretch of road, a different challenge and another part of Justin’s story. Follow along as Skyler continues pushing toward his September 3 finish.
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