Two skateboarders embark on epic journey along the 444-mile Natchez Trace Parkway

Moondog Roop and Justin Bright skateboarding along the Natchez Trace Parkway
(Image credit: David Roop)

Welcome to the world of thru-skating. Never heard of it? Well, you can probably guess what it means, but if not, we’ll let one of its most enthusiastic proponents, David 'Moondog' Roop, tell you: “It’s essentially long-distance hiking on a skateboard.”

And currently Moondog Roop and fellow skateboarder Justin Bright are undertaking just such an epic feat of endurance skateboarding.

They’re about to complete an epic two-week, 444-mile journey along the Natchez Trace Parkway in Tennessee and Mississippi on their boards – the first people to do so. And Roop also intends to carry on a further 90 miles to Baton Rouge, reports CW39. They began their wheeled voyage on 3 October and are on course to complete it on 17 October. 

“We are really just doing this to have fun and because it hadn’t been done,” says Roop. “Someone mentioned this trail to us, and within hours we had decided to do it.”

It’s not even their biggest skateboarding trek. They first met when they were both individually skating 1,100 miles of the Florida Trail in 2021-2, and have since also skated almost 500 miles around New Mexico, Roop’s home state.

Roop, who was already a seasoned thru-hiker, was inspired to take up long distance skateboarding after hearing about Alex Fogt hiking the Florida Trail with a skateboard in 2018. He had to learn how to skateboard first, but now he truly has the bug.

Carrying tents, food and water, Roop and Bright only get off the road to eat, recharge their electronic devices, buy supplies or sleep.

“In the hiking world we’re known as ‘hiker trash’,” says Roop. “Basically meaning we will sleep anywhere, eat the most unhealthy food and drink the sketchiest water. It’s a title that is earned and worn with pride.”

Their gear is built for long trips and rough treatment. Roop is using a “Pantheon Quest longboard with the new Pantheon Karma wheels,” and Justin has a board by Underground Longboards with Oragatang Caguama wheels.”

For Roop, it’s now the only way to travel, so long as you don’t need to get somewhere fast. “Skating is definitely our favorite form of travel. Have you ever seen someone frowning on a skateboard? Me neither.”