Over the past few years, Moondog Roop has done three major thru-skates. First in 2021, he spent 45 days on the 1,100 mile Florida Trail. In 2022, he thru-skated across the entire state of New Mexico, and in 2023 he skateboarded 444 miles on the historic Natchez Trace, a trail which passes through parts of Tennessee, Alabama, and Mississippi.
Over the past few years, Moondog Roop has done three major thru-skates. First in 2021, he spent 45 days on the 1,100 mile Florida Trail. In 2022, he thru-skated across the entire state of New Mexico, and in 2023 he skateboarded 444 miles on the historic Natchez Trace, a trail which passes through parts of Tennessee, Alabama, and Mississippi.
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Moondog Roop:
When you're tired and you're just hiking, you have to keep going. And so there's nothing to really break up the monotony. So the benefit of bringing the board is that whenever I hit a road, I put the board down, I start skating. So it really doesn't matter what my day was like. When I hit that pavement, it just starts being fun again.
Shelby Stanger:
Recently I got an email from Moondog Roop telling me about a wild idea he's been chasing, called thru-skating. Thru-skating is like thru-hiking, but with a skateboard. At some point, most thru-hikes hit pavement and hikers have to walk through towns or on the side of the road to find the trail again. Moondog alternates between hiking the trail sections and skateboarding the paved parts. Personally, I think this is genius and one of the most unique wild ideas I've heard to date.
I grew up skateboarding, and I love that thru- skaters bring some childlike fun to long distance treks. Of course, it's also a big commitment. Carrying a board and a helmet can easily add another eight pounds of weight to your pack. And unlike food, that weight never gets any lighter. Maybe that's why there aren't that many people doing it. Moondog estimates that he's only one of a handful of thru- skaters in the country. Just to note, Moondog is his trail name.
I'm Shelby Stanger, and this is Wild Idea's Worth Living an REI Co-Op Studios production brought to you by Capital One.
Over the past few years, Moondog Roop has done three major thru-skates. First in 2021, he spent 45 days on the 1,100 mile Florida Trail. In 2022, he thru-skated across the entire state of New Mexico, and in 2023 he skateboarded 444 miles on the historic Natchez Trace, a trail which passes through parts of Tennessee, Alabama, and Mississippi.
The concept of thru-skating wasn't so foreign to Moondog. He's been hiking since he was a kid, but he only started skateboarding when he was 33 years old.
Moondog, welcome to Wild Ideas Worth Living. You are our first thru-skateboarder ever on the show.
Moondog Roop:
Thank you. I'm glad to be on and it's nice to be the first, I guess.
Shelby Stanger:
So okay, skateboarding, thru-skateboarding. I'm so excited to talk to you about this because like I said, you are our first, and I read that you didn't start skateboarding until you were an adult. Is that true?
Moondog Roop:
Yeah, I actually picked it up almost four years ago and picked up for my 33rd birthday because a friend just had his first kid and whenever we were growing up he would always skateboard and I was too afraid to actually do it. And so when he had this kid I was like, he's going to teach this kid how to skateboard, and so I want to be able to do it together with them and so I started skating and so it all kind of worked out.
Shelby Stanger:
So isn't learning to skateboard as an adult hard?
Moondog Roop:
Yeah, actually a little embarrassing as well, because when you're around other skaters, they're generally pretty young and if they fall down they could get right up. If I fall down, I'm going to lay there for a couple minutes and maybe consult a physician or something like that.
Shelby Stanger:
And when we talk about skateboarding, you're not going to a park and using a short skateboard down ramps, you are riding a long board.
Moondog Roop:
Actually, I pretty much just, yeah, just starting out, just kept to the streets and it was actually about the time that the Covid shutdowns were happening and so nobody was really driving, so I would just skateboard on the streets with no cars, which was one of the benefits of a dark time, I guess.
Shelby Stanger:
So what was the learning process like? Any injuries?
Moondog Roop:
Actually, I did break three ribs skating. Actually, almost exactly three months before I started the Florida Trail. I just was skating along, it wasn't really paying attention and happened to fall. I Just fell in the worst way. And actually whenever I broke the ribs, I basically had to just lay in bed as much as I could and I was just laying there thinking about skating and that's whenever I was like, okay, this is actually something you really love.
Shelby Stanger:
As Moondog recovered from his injury, he knew it was time to make a change. He took the money he'd saved up from work and set out on his first ever thru-skate. Moondog decided to do the Florida Trail, which has 800 miles of dirt and natural terrain and 300 miles of paved roads. While thru-hikers dread pounding their feet on the pavement, thru-skateboarders can pull out their board and roll right along. For this thru-skate on the Florida Trail, moondog started in Pensacola and made his way 1,100 miles south to the Everglades. The trip was life-changing.
Okay, so first you did the Florida Trail, which probably was incredible. Do you have any highlights from that one?
Moondog Roop:
Actually, yeah, I made so many good friends on that trail. I was actually hiking it alone and just happened to meet a big group of people and we ended up becoming friends and almost all of us talk on a weekly basis. We're just still in the same little group chat and we always share what we're doing, where we're at, things like that. I just made some incredible friends on that trail.
Shelby Stanger:
Was there any misadventures?
Moondog Roop:
The only real misadventure is you're kind of wet all the time, so it constant humidity, it rains a bunch, even hiking in rain.
Shelby Stanger:
My experience with skateboarding is that when it rains, it's no fun to skateboard in the rain on wet pavement.
Moondog Roop:
Correct, yeah. You're still wet. Actually, on a skateboard, it's actually a little bit worse because my back tire kicks water up directly into my shoe, so my right shoe is always wetter than my left.
Shelby Stanger:
And isn't it like slippery? Do you ever skid out?
Moondog Roop:
Yeah, a great thing about the wheels that we use is they are actually fantastic at gripping, so it's not necessarily like you would have on a just regular skateboard deck, but you do go slower and you do still have that possibility. I try to watch out for wet leaves and things like that, but it'll hold to the pavement pretty good. The problem is slowing down if you have to put your foot down to slow down, it doesn't work as well, so you got to be a lot more cautious.
Shelby Stanger:
So for people who are just still completely clueless on how this works, let's talk about the Florida Trail. What does it look like and what are you riding? Are you just riding in the bike lane on a big road?
Moondog Roop:
Yeah, so I would hike all the trail sections and I had a regular, it's called Popsicle Stick kind of deck that was strapped to my backpack and then whenever I would hit a road section, I'd take the board off and I would skate that.
Shelby Stanger:
Oh, so you're going way faster than regular hikers?
Moondog Roop:
Yeah, I can generally skate on that kind of deck at about five to six miles an hour.
Shelby Stanger:
Okay, I love that. What did you learn besides, did you have any epiphanies about yourself, work, life transformation on this Florida Trail?
Moondog Roop:
Yeah, I realized, I don't know if you've ever heard of the term hiker trash, but it's a very positive term for hikers that can sleep in the dingiest of places, can live as cheaply as possible, really just have honed in their gear and things like that. And so on that trail I realized I was definitely hiker trash and I really quite embraced it and it was like this should be more of a lifestyle for me than the one I was living beforehand. And even beforehand, I don't think I was living a terrible lifestyle, but I was just like, this is definitely the happiest you've ever been.
Shelby Stanger:
So you realized that you could live with less and enjoy more?
Moondog Roop:
Exactly. And I was actually pretty much a minimalist before. I lived in a van, still live in a van, and so I didn't have a lot, but I was like, "Oh, even that feels like too much. Let's scale it back a bit."
Shelby Stanger:
thru-skating the Florida Trail allowed Moondog to reflect on his life, his career, and where he finds joy. But what happened after the trip was nearly as transformative. Once some friends caught wind of what Moondog was up to, they introduced him to another thru-skater named Justin. You know that moment when you meet someone who you can tell is going to be your best friend? That's what happened when Moondog met Justin. Within 24 hours of meeting each other, the two decided to go on a thru-skate together across the entire state of New Mexico.
What did skateboarding all of New Mexico look like?
Moondog Roop:
So we met in El Paso and we had kind of a rough outline of what we were going to do, but it was real kind of rough. We knew basically two days ahead of where we would be, and then we just kind of figured it out from there. We knew we were going to follow the Rio Grande so that we could have water access the whole time, and so we had a general idea, but we just kind of figured it out as we went along. And so then that way if we hit a road that wasn't great, like the pavement was bad or something like that, we could change path and go somewhere else.
Shelby Stanger:
Where did you sleep? What did you eat?
Moondog Roop:
So I'll start off with eating because that's actually easier to explain. We ate basically foods that you would eat when you're doing a thru-hike, really unhealthy foods that we'd carry with us. Big fan of candy. And we also eat at quite a lot of restaurants. One of the benefits that the skateboards allow us to do is go further in a day, and so we can hit towns a little bit sooner. And so there's times where we will be skating through a town at breakfast and we'll be like, maybe we should grab something to eat while we're here, and then we skate another 40 miles and you've hit a town for dinner time. So we're like, ah, maybe we should eat here. And so we really enjoy that about our trips.
So in New Mexico, we actually spent a lot of time sleeping under bridges. I think it was our second night that we were on trail, Justin was like, we would pass the Rio Grande, and he pitched the idea that we sleep on the dry water bed. And I was like, "Man, I'm not sleeping under a bridge." And we had this big back and forth about it and he won and so we slept under the bridge that night and we were just hooked. We just thought it was so much fun, kind of like being in a fort when you're a little kid. And so we did that pretty frequently. Other than that, we just do cowboy camping where you just sleep out under the stars.
Shelby Stanger:
Can you describe some of the scenery you saw?
Moondog Roop:
Yeah, so in the bottom of the state it's a lot of flatland desert and you see a lot of the influences of Mexico there, where it's more like adobe houses and then as you start going further north, it becomes more high desert, and so you start getting more mountains. But it is kind of deceiving because you're still out in the desert, you're just higher up. It feels a little bit colder, a little bit more wind, things like that.
Shelby Stanger:
It sounds beautiful. Was there anything on that trip that really stuck out?
Moondog Roop:
I would say probably the biggest story of that trip is the place I live now happened because of that trip. I live in a little town called Madrid, New Mexico, and it was actually just a stop along the way in which we were going to get water, and we were on the edge of town actually refilling our water bottles, and somebody that we had seen driving past us, like the day earlier, she ended up seeing us and she was like, "You all should stay the night and go to hip hop night." And so this is a town of 300 out in the middle of the desert and they had hip hop night and we ended up getting talked into going to it, and it was the most fun I'd ever had. And it was a little bit later that night, I was like, "I think I'm going to move here." And we were going to leave the next morning, made our way back into town and ended up staying another day just hanging out in town, talking with people, and it's just so much fun. So about three months after that, I ended up moving to Madrid.
Shelby Stanger:
And what is hip hop night? What does that consist of?
Moondog Roop:
It's like Santa Fe rap artists that all get together and the guy that runs it has the best rapper name, O.G. Willikers, and so he runs this hip hop night and it's so much fun and there's people that are there that are 18 years old. There's people that are there, they're like 75, and everybody's just there to enjoy hip hop and the town and the night and enjoy each other.
Shelby Stanger:
Hip hop and New Mexico by O.G. Williker, that is a very unlikely hip hop name. It sounds like a Saturday Night Live episode, but I love it. Talk to me about the difference between skate hiking and hiking. What are the benefits?
Moondog Roop:
So the benefit of bringing the board is that whenever I hit a road, I put the board down, I start skating. So it really doesn't matter what my day was like, when I hit that pavement it just starts being fun again. And if I get tired of skating, I can pick up the board and start walking.
When you're tired and you're just hiking, you're just tired and hiking, you have to keep going and so there's nothing to really break up the monotony. On the adverse side, the con of having that board with you is while you're hiking, it's basically just like a five or six pound paperweight. It doesn't do any purpose out in the woods.
Shelby Stanger:
Except for maybe you can sit on it. Yeah, I was thinking about that. It seems like you put that skateboard down and it's instant fun and play. It must trigger this reaction in you. For me, every time I skateboard, I'm a little kid again.
Moondog Roop:
Right yeah, the magic never goes away and it doesn't matter how bad your day is, you don't see people frowning on a skateboard.
Shelby Stanger:
When we come back moondog talks about his most recent wild idea to thru-skate the Natchez Trace and he shares his tips for people who want to try thru-skating.
For Moondog Roop, the last few years have consisted of a series of wild ideas. He started skateboarding, left behind an unfulfilling career, took up thru-skating and moved to New Mexico. Now he works as a carpenter around town to save up for his thru-skating adventures.
Moondog and his friend Justin recently spent 12 days skateboarding the Natchez Trace together. The Natchez Trace is a 444 mile scenic trail that passes through Tennessee, Alabama, and Mississippi. It's completely paved, almost like a parkway that bikes and skateboards can also ride on. Moondog and Justin started their trip in Nashville on October 3rd.
So you decided to do the Natchez Trace. What kind of prep goes into something like that?
Moondog Roop:
So kind of ignorantly, we don't do a whole lot of prep. One of the things that actually I like about skating with Justin, we have the same skill sets in the ability to sleep in tents wherever. Basically the backpacking and being hiker trash kind of skillset, we know how to get out of emergencies if we're in an emergency and we trust each other a lot. And so that really helps with our skating, kind of making it more fun.
Shelby Stanger:
How much did you skate every single day?
Moondog Roop:
It ended up taking us about 12 days. I think we ended up skating about 40 miles on average.
Shelby Stanger:
Is that tiring? Do you get tired skateboarding?
Moondog Roop:
You do. Your legs get kind of sore the same way in which they would if you're hiking all day, it's just a different set of muscles, and so we're generally pretty tired. But you could actually skate a lot more. Forty miles is basically us keeping a good pace, but still having fun. We're big fans of the goof off, and so we goof off constantly.
Shelby Stanger:
So what's a typical day? You wake up and then just like talk me through it. How long does it take to skateboard? When do you stop? What do you eat?
Moondog Roop:
So when we wake up, we generally lay in bed for about half an hour, just kind of groaning and drinking coffee, and then we get up and start packing up. We're generally kind of slow. We just goof off a lot while we're doing everything and we kind of talk about our route just a little bit. And then we just start skating. The morning time is some of the best time to skate because there's generally not as much traffic. You're a little bit cold, so you want to warm up a little bit, and so you're just kind of cruising and enjoying skateboarding. And so we carry a lot of snacks on us while we're skating, so we typically don't stop until we get to about lunchtime.
Shelby Stanger:
Okay. So you hike about 40 miles a day, you break it up with some lunch, then you have dinner, then you find a place to camp, and you're camping anywhere.
Moondog Roop:
Correct. We generally look for designated campsites. We actually do get invited into people's homes quite often. People will just think it's interesting what we're doing. Actually, when we were in New Mexico as we were going by a brewery, there was a guy that popped out and he asked if we were skateboarding. We're like, yeah. He's like, "Oh man, I'm getting off work right now. You want to go?" And we're like, sure. So he went in and grabbed it and we just started skating with him like a minute after we met this guy and within three minutes of knowing him, we had agreed to stay at his house that night.
Shelby Stanger:
Moondog and Justin have met tons of people while thru-skating. Some are curious about skateboarding, some invite them in for a sandwich and some become friends. Most of their interactions are positive, but of course there are important safety concerns that the pair take very seriously. For example, when Moondog is skating on the road, he communicates with drivers using his body language. He says it's safest to take up lots of space. Moondog rides down the middle of the lane, and when cars come up behind them, he waves them past. There are also some more basic things to consider that make things easier for thru-skaters on the trail, like dialing in their gear and getting comfortable with changing conditions.
For people listening who want to get into thru-skateboarding, what are a few things they need to know?
Moondog Roop:
It would be incredibly beneficial to have skill sets that are like thru-hikers. So you actually need to have all of your gear pretty dialed in. So you don't want to be skateboarding with a 30 pound pack because the second you hit a gravel, it's all over. You just have to be good at being outside in uncomfortable situations. When it rains, we're just getting wet, but just still have to keep skating. And I think that's a huge skillset, is just being able to kind of deal with the suckiness that's out there.
Shelby Stanger:
How many people do you think are out there thru-skateboarding? How many thru-skateboarders are out there?
Moondog Roop:
I would actually speculate that it's less than 50. I would almost say it's probably like 12 people, but there's got to be people all over that we just have never heard of. I met a guy in Florida and unfortunately, we didn't get long to talk because we were just kind of passing by at the wrong time, and he was just brought a skateboard on the trail with him, told nobody about it. Nobody had really met this guy or heard of him or anything like that, but was just out there doing it himself. And so I think there's a lot of people that are out in the world doing something similar but don't have social media and just never talk about it.
Shelby Stanger:
Tell me about gear. What are you guys using?
Moondog Roop:
The boards that we use are built for long distance and they're effectively just built to go really far in a straight line. So the board is pretty straightforward, just things that could do lots of miles. We don't particularly worry so much about weight with boards. Our packs, we use ultralight packs, we sleep on ultralight mats and everything that we bring is a good balance of both weight and comfort. And so everything's dialed in just as much as we can get it.
Shelby Stanger:
So what backpack are you using? What brand?
Moondog Roop:
So I actually have a custom-made backpack that was built for me that can hold a skateboard, so it actually has a special flap on it that could be opened up and then I can strap the board to it.
Shelby Stanger:
What about shoes? Are you wearing hiker shoes or are you wearing skate shoes?
Moondog Roop:
I actually wear trail runners and I wear the same pair for hiking that I do for skating. I wear Ultras.
Shelby Stanger:
I wear those too.
Moondog Roop:
Yeah, they're great. And you actually get about the same mileage on a skateboard as you would hiking with shoes, but I always wear down my right one faster.
Shelby Stanger:
Because your right one is pushing?
Moondog Roop:
Right and stopping and yeah.
Shelby Stanger:
Are you listening to music? Do you bring music with you?
Moondog Roop:
I do. So because we're on the road, we bring, we generally just put one headphone in and then leave our right ear for listening to traffic. But we do typically like to listen to music and I just have a playlist of songs that are fun to skate to, and I just kind of play it over and over and just enjoy being out there. Everything's just like an upbeat, fun song. And then him and I do a whole lot of just talking to each other and we joke around constantly, so we're basically just telling jokes and making fun of each other.
Shelby Stanger:
Hearing Moondog talk about thru-skating warms my heart. I love how he's made choices that bring more joy into his life. Moondog is living proof that it's not too late to try a new sport. If you're interested in skateboarding, do it. Please be safe. Wear a helmet and pads and start slow.
If you want to learn more about thru-skating and Moondog's life in general, check them out on Instagram at RoopTown, that's R-O-O-P-T-O-W-N. There you'll find chronicles of his journeys on the road and so much more.
If you like this episode, check out our episode from 2016 with Cindy Whitehead, who skateboarded down the 405 Freeway Wild Ideas Worth Living is part of the REI Podcast Network.
It's hosted by me, Shelby Stanger, produced by Annie Fassler, Sylvia Thomas, and Sam Pierce Nitzberg of Puddle Creative. Our senior producers are Jenny Barber and Hannah Boyd, and our executive producers are Palo Motala and Joe Crosby.
As always, we love it when you follow this show. Take time to write a review wherever you listen. And remember, some of the best adventures happen when you follow your wildest ideas.