HomeWhy Trail Running Feels Like Skateboarding but Isn’t

Why Trail Running Feels Like Skateboarding but Isn’t

Trail running culture is starting to look a lot like skateboarding—crews, aesthetics, a more raw identity.

But if you’ve ever wondered whether that comparison actually holds up, this episode breaks it down.

There’s a reason the connection feels right—and a deeper reason it might not be. This isn’t about dismissing what’s happening in running, but trying to understand what it actually is.

This episode is for runners who care about the culture of the sport, not just the miles.

Please give us a follow, rate the podcast, and give a review.

Presented by Kiprun.

 

Topics / Timestamps

  • 1:20 Culture and Identity in Trail Running
  • 4:19 The Shift from Results to Experience
  • 06:41 The Intersection of Trail Running and Authority
  • 10:21 The Intersection of Skate Culture and Trail Running

Resources / Links

Related Episodes

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Transcript
Speaker A:

People keep saying that trail running is becoming like skateboarding.

Speaker A:

It's more raw now.

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It's more about the cruise, more about identity than structure.

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And if you look at it, it kind of checks out.

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The footage looks familiar, the energy feels familiar.

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There's something about it that feels real, no doubt.

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But I think there's something off in the comparison, because what made skateboarding culture real was never how it looked.

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It's like the idea from SLC Punk, if you ever saw it.

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The most punk person in the room isn't the one who looks the part.

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It's the one who doesn't need to.

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Sometimes the truest punk rockers wore a suit and tie.

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You remember that dude in the movie, more punk rock than anybody else had a day job, wore the suit and tie because rebellion isn't aesthetic.

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It's rejecting something you don't like.

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The aesthetic of rebellion is what it is because they were dressing in a way that pushed against a status quo that was making itself other than the status quo.

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A status quo.

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Or maybe it was a statement of the abomination of a status quo they wanted to preserve.

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And that's where this starts to feel different.

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Because trail running can copy the look, the grain, the crews, the attitude.

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But trail running still has to ask permission.

Speaker A:

The Borderlands Trail and Ultra Running podcast, presented by Kip Run.

Speaker A:

My name is Josh Rosenthal.

Speaker A:

If you haven't checked them out yet, take a look at the new Kip Run trail shoes called Kip Summit.

Speaker A:

They're thoughtfully designed, built to handle legit distance, and genuinely just a joy.

Speaker A:

And speaking of joy, I would really love, if you are enjoying this show, that you would give us a follow or subscribe wherever you're listening.

Speaker A:

And if you can, leave a rating review, it really helps grow the show.

Speaker A:

All right, so this idea that running is becoming like skateboarding, I keep coming back to it, and I get why that comparison shows up.

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Because if you've ever been a part of something like that, something that has had its own rhythm, its own identity, its own sense of belonging, you don't forget it.

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Like being somewhere you're not supposed to be.

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Sun going down, everything's still there.

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No one really saying it out loud, but nobody wants to leave that feeling that something is happening and you're inside of it.

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It's an incredible feeling.

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For me, that was ages 13 to, like, 17, 16 years old.

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You spend a long time trying to find that feeling again, whether you realize it or not.

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And when something in running starts to look even remotely like it.

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Crews forming Shared language, certain kind of energy.

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It's hard not to reach for the comparison, to say, this is it, this feels like that.

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But I think there's something off in the connection.

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But before you even get into whether that comparison is right or wrong, it's worth looking at why it simply feels right and celebrate the reasons that it feels right.

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Because visually, trail running has moved in a very specific direction lately.

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At least the bulk of it.

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Grainy footage, handheld cameras, blurred photo edits, moments that feel captured instead of produced.

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It doesn't feel polished, it feels immediate, like someone pulling out a camera, maybe mid run.

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Not to capture a result, not a finish line, but just because the moment feels worth remembering.

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And that language is familiar because skateboarding already built it.

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And it goes beyond visuals, too.

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Crews instead of clubs, you know, identity built around who you run with.

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Not even just where you run, but who you run with.

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Moments that matter more than results.

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That's huge.

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Right now, even the imagery has shifted away from the finish lines towards something in the middle.

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Effort, atmosphere, being there.

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Because all of that signals the same thing.

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This is real.

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And that's why this comparison is so compelling.

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Because when something looks real, it's easy to assume that it is.

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And to be fair, that doesn't happen by accident.

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Something real is happening here.

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This isn't just brands manufacturing a look out of nowhere.

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You see it in the way crews are forming organically, groups that aren't built around races like, you know, Sam Losey and his crew.

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Active cultures meeting at the track every week for an early morning speed work session.

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But it's around, showing up together week after week, same people, same time.

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You start to recognize faces that were once unfamiliar.

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You become friends with them.

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You know who's going to be there before you even show up.

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Not because they have to, but because they want to.

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They often have family and lives, and it's really hard, but worth prioritizing it.

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And you see it in the way people linger around it.

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The run isn't the whole thing anymore.

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People stay, they talk, run clubs built around what you do before it or what you do after it.

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They hang out extends well beyond the miles and kilometers.

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And you see it then most vividly in how it's documented.

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As I said, not the finish line, not the result, but the middle, the effort, the feeling of being there.

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And if you're inside of that, it probably doesn't feel manufactured at all.

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It feels like something you're building.

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But even if all of that is true, trail running still depends on permission to exist.

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Skateboarding never did.

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And once you see it that way, a lot of things start to look different.

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In skateboarding, the environment is something you push against.

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Streets, rails, stairs, things that weren't built for you.

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And frankly, you're not welcome at.

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In trail running, the environment.

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In trail running, the environment is something you move through, something you rely on staying opened, maintained, accessible.

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In skateboarding, getting kicked out is part of the experience.

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But in running, losing access affects everyone.

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In skateboarding, it's a.

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It's a crown to get kicked out.

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It's footage and running, you lose access for everyone.

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You shut down a trail, that's not just your moment, that's everyone's morning.

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And the relationship to authority is very different.

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In skateboarding, authority is often the obstacle.

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In running, authority is part of the system.

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Land managers, permits, organizations, they're not something you push against.

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They're part of how this exists at all.

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It doesn't really seem like a culture built on pushing against authority.

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It seems like one that works with it.

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And if that's true, then it also explains something else.

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Because once something lives inside a system, it can be shaped by it.

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Refined, distributed, sold back in a form people recognize.

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And that's what's happening here.

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The moment this look becomes identifiable, it becomes something you can buy into, commodify not just the gear, but the feeling of it, too.

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A singlet that looks worn in a hat that feels like it's been through something.

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It's designed to feel undesigned.

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It's designed to feel used before you use it.

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And that's the shift.

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What used to be a byproduct worn in gear holes is now something you can access directly.

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You don't have to live it.

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You can just step into it.

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And that's not necessarily a bad thing.

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It just changes what it is.

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And at a certain point, it starts to feel like something else, like we're not actually doing the thing.

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We're presenting ourselves as if we're doing the thing, but we're not doing the thing.

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We're wearing the stuff.

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We're signaling, you know, properly.

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Our Instagram feeds look correct without ever having having to deal with what made it that way in the first place.

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So the question becomes, what are we actually looking at here?

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Because if this sport operates differently, it depends on access, on shared systems, on a relationship with the land, then it's not missing something, it's just something else.

Speaker A:

And maybe that's enough.

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And maybe I'm not the perfect person to say any of this.

Speaker A:

I came up in a completely different world.

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West Texas, sparsely populated punk rock shows.

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Some of them were the ones that I was playing, some that we were attending.

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Psycho ska bands traveling through, playing in little tiny warehouses, chasing moments that felt like it mattered.

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Skateboarding.

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So maybe part of this is just me recognizing those things don't Translate cleanly.

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This 90s skateboard vibe just doesn't translate cleanly to trail running, like many are trying to make it.

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But I do know this.

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You can copy how it looks, you just can't copy what it means.

Speaker A:

Do you agree?

Speaker A:

I'd love to hear from you in the notes and the comments.

Speaker A:

This is meant to be a reflection on 90s skate culture being infused into trail running and those who are trying to do it.

Speaker A:

Hoping to foster conversation and if nothing else, just an interesting conversation.

Speaker A:

Interesting look at the industry.

Speaker A:

See ya.

Written by

Founder of Borderlands Trail Running, Host of the Borderlands Trail +Ultra Running Podcast