The world opens up to David Roop when he rides his longboard long distances.
Roop, who goes by the trail name Moondog, picked up thru-skating in his mid-30s and now has the pleasure of explaining what that is to curious townsfolk when he rolls in with his backpacking gear and an eye out for a good time.
It’s not all that hard to describe. Thru-skating is basically thru-hiking or bikepacking but with a skateboard. In Moondog’s case, it also involves embracing chance opportunities, accepting invitations into strangers’ homes within minutes of meeting them and getting into serendipitous adventures.
“If you try to stay too much on a certain path, you kind of control what’s happening, and you’re not opening yourself up to what’s unexpected,” said Moondog, a 36-year-old former hearing aid specialist who grew up in Eastern Tennessee.
Taking what the path gives has led Moondog to new friendships, countless stories and finding a new home in New Mexico since he began skating just a couple of years ago.
He recently calculated that he’s put about 2,000 miles on his Pantheon longboard in a year and a half. That includes a 24-day, 492-mile thru-skate of New Mexico in the spring of 2022 and a skate on the 444-mile Natchez Trace Parkway — a National Scenic Byway between Nashville, Tenn., and Natchez, Miss. — that he just finished in October.
Both odysseys were taken with thru-skating compadre Justin Bright, who Moondog met while on his first thru-skate in the winter of 2021-22 on the 1,100-mile Florida National Scenic Trail.
While thru-hiking and bikepacking have ballooned in popularity in the last decade, thru-skating is a much more novel form of adventuring that a small number of people participate in.
Moondog and Bright are the first two people known to have skated the full length of the fully paved Natchez Trace. They’ve become thru-skating ambassadors of sorts, promoting long-distance skating as an option for those who love to be on their boards and offering tips to people who have reached out on social media with inquiries about gear and trip planning.
Four to five years ago, before he became Moondog, Roop read about a man named Alex Fogt who brought his skateboard on the Florida Trail, which passes through the swamps, forests and prairies of the Sunshine State. About one-third of the trail is road or bike trail, which allowed for him to take his 5.2-pound board off of his pack for stretches and skate instead of hike.
To most ultralight backpackers, carrying the extra weight of a skateboard for two-thirds of a thru-hike would be considered insane. Roop had a different view when he read through Fogt’s first-person account and saw the many gator-, swamp-, and skate-filled photos included from the trip.
“I didn’t even know how to skate at the time, but I was like, ‘This sounds amazing,’ ” he said. ”It was just one of the coolest things I’d ever heard.”
Roop was already an avid hiker who knew what to expect and how to plan for long trail treks. He soon learned how to skate and, inspired by the article, built up the confidence to try to replicate Fogt’s feat.
Roop had the time of his life in the nearly eight weeks it took to complete the trail. He also gained the trail name Moondog and had the chance to meet Bright, who was skating across Florida for charity. The two became fast friends and made plans to thru-skate New Mexico together two months later.
They chose the Land of Enchantment because they hadn’t been there before and wanted to see what it was all about. They had a general idea that they’d follow the Rio Grande from El Paso up to the Colorado border but weren’t bound by any set route or time limitations. They’d just stick to the less-trafficked roads to get the most enjoyment out of the experience and sleep outside wherever they could find a place to rest their heads.
“You don’t really make plans that far ahead besides your food and water and what you need to survive. Everything else is just kind of left up to chance,” Moondog said. “That’s kind of how we like to do it. You just have complete freedom.”
What they found in New Mexico was welcoming people, incredible landscapes and absurdly strong spring winds.
“There were days where we would be going downhill and there was such a headwind that it would stop you, so it was almost worth walking because there was so much wind,” said Moondoog, who made the trip from late March to early April 2022.
Longboarding on rural roads and through small towns with a pack on your back is a pretty good conversation starter, they found. Throughout their journey, Moondog and Bright were approached by colorful characters who offered them a glimpse of life in the towns they call home.
While passing through Truth or Consequences they were stopped by a man who was just getting off work at a brewery. He asked what they were up to, then got out his electric longboard and started skating with them. Within three minutes of meeting, he had invited them to stay the night at his home.
The man shared with them the story of how his vehicle broke down in Truth or Consequences some years back. While waiting for a part for the repair, he fell in love with the town and decided to move there.
Also in T or C, a middle-aged woman hollered at them to come over as they were going by her house. Within 30 seconds they were inside, and she was telling them that she’d had a premonition about them coming through. The woman had some friends over, and they all spent the afternoon telling Moondog and Bright about their interesting little town.
Later in the trip, the skaters were expecting to spend about an hour in Madrid to resupply with food and water while riding up the Turquoise Trail on their way to Santa Fe. They got to talking to a local who said they had to go to a hip-hop night and dance party at the Mine Shaft Tavern. Moondog said he was tickled to learn that a town of a few hundred people had a hip-hop night at the local bar.
“A few hours later I was like, ‘I think I’m gonna move to this place,’ ” Moondog said. “It was one of the best concerts I’d ever been to. It was just so much fun.”
They ended up staying in Madrid for a couple days, sleeping in the dugout of the old ballpark and hanging with the locals of the artsy, quirky former mining town.
A few months later, Moondog did indeed move to Madrid. Since there’s no hearing aid industry in Madrid, he does general labor ranging from landscaping to building projects. He said the work supports his lifestyle of travel and adventure.
Moondog soon plans to take a solo trip to Puerto Rico, where he’s going to see if it’s possible to skate the 300-mile circumference of the island. A Santa Fe outdoors store called Tourist that supported him with gear and food on the Natchez Trace is shipping him some gear for the journey.
Next year, Moondog wants to try to do a thru-skate version of the Continental Divide Trail, making his way about 3,000 miles from the U.S.-Mexico border all the way up to Canada.
Moondog said he hasn’t really had any issues with drivers while on his thru-skates. They tend to get out of the way and leave room for him when passing, which usually isn’t hard on rural roads. And it’s easy to look both forward and back while standing sideways on a skateboard, he said.
Moondog gets excited when he thinks about the possibilities of thru-skating. It’s truly a choose-your-own-adventure activity, he said, allowing a person with the right skills to string together roads and trails through beautiful, interesting areas and fashion epic experiences.
While thru-hikers may average 10-20 miles per day, Moondog said he can go 40-50 miles on his longboard, which expands his opportunities.
Though he’s able to cover ground faster while skating, the potential for chance encounters is still much greater on a board than it would be if he were traveling by car. It’s those moments getting to know people, and in turn getting a real feel for a place, that Moondog said really stick with him from his journeys.
That’s how he settled on his new home in New Mexico. Drawn in by hip-hop night at the Mine Shaft, he got to know how fun Madrid and its residents can be.
A year and a few months after making the move, he said he’s loved every minute of it.
“I think it’s one of the last Wild West-type places where anything goes and people are eccentric,” Moondog said. “It’s definitely lived up to what I thought it was going to be. It’s an amazing place. It’s definitely weird, but it’s weird in the right ways.”