The Joey Okesson Interview

-Continuing The Long Line Of Darkside Halfpipe Riders-

Story // Jake Sullivan. April 3, 2025

Joey Okesson - Steamboat Springs - photo: Jeff Urbahn

Throughout the 90s and early aughts, Killington and Okemo consistently had some of the best halfpipes in the country, spawning generations of riders that would go on to shape snowboarding in various ways. Danny Kass, Lane Knaack, Abe Teter, and many other massive names in our world cut their teeth in these icy ditches in Southern Vermont. At Darkside, first-generation team riders like Mark Reilly, Aaron Carr, and Brian Regis would be seen hiking Killington’s pipe on Highline any given day back then, absolutely destroying it.

Aaron Carr - Killington - Late 90's

Brian Regis - Stratton - photo: Gary Land

Aaron consistently did some of the biggest airs I had ever seen in that pipe when I was young, and legend has it he tapped a K1 gondola car on a backside air. Mark Reilly and Brian Regis made everything they did look so good, eventually moved to Mammoth, put out multiple video parts, and got photos in the magazines. Mark even landed the cover of the Feb 2002 issue of Transworld Snowboarding.

Mark Reilly - Killington 90s - photo: Gary Land

The next generation included myself, Graham Bayne, and many others, flying the shop’s flag high. Being the token halfpipe guy in the crew, I eventually found myself in Grand Prix starting gates above some of the country's best halfpipes, and even a US Open final one year, strapping in next to some 15-year-old Japanese prodigy named Kazu Kokubo. The whole time, though, we all represented Darkside as hard as we could.

Jake Sullivan Airing over Graham Bayne - 2005 Killington Promo

When I moved back to New England years later and started to immerse myself back in the East Coast snowboard community, people kept telling me about this kid to keep an eye on. He was a halfpipe rider from Okemo who repped the shop super hard, named Joey Okesson. My first time seeing him ride was watching the 2020 US Open, where he stayed on his feet for his third run, ending it by stomping a massive front 10 landing him in 5th place.

Then, in the corral at the bottom, he held his board up to the camera showing a Darkside sticker and yelled Darkside into the mic. I loved it. The announcer on the broadcast was saying how stoked Joey must’ve been to put a full run down on his last attempt at his first US Open. I knew exactly what he meant as I had been in the same position as Joey 16 years before at the same event. I hadn’t met the kid yet, but I had his back from there on out.

Joey Okesson - 2020 US Open - photo: Cole Pates

For the past few years, he has been competing on the halfpipe circuit, traveling the world as part of a small elite group of about 30 men and women riding at the highest level ever seen. He is helping to write the book for this modern era of halfpipe snowboarding while keeping his own unique style and East Coast mentality at the forefront. We are stoked to have him flying the Darkside banner and adding his name to the long list of halfpipe riders who have represented the shop over the years.

He stopped by the shop to sit down and fill us in on his season and share some of his thoughts on the world of competitive halfpipe snowboarding today. Check it out!!

Dude, thanks for coming by! It looks like you’ve been traveling nonstop this year. Where have you been and what have you been doing?

Joey: I've been bouncing around. I spent a lot of time in Colorado and Switzerland. Just chasing the halfpipe scene.

You competed in the inaugural Snow League this season. Shaun White's new high-profile halfpipe event. What were your initial thoughts?

Joey: It felt like a modern-day US Open. They even hired a bunch of people that used to work that event, so everybody knew what was up. Lots of familiar faces and people who are passionate about snowboarding and competition.

The format was unique, with the head-to-head matchups. How was it from a riders perspective?

Joey: I was pretty stoked on the run I did, but didn’t get scored too well. I had a conversation with the judges after the fact where I spoke my part, and it was well received. There’s such a big disconnect between the industry and competition - one reason being spin to win is king. I feel like this event is a chance to make competing cool, while showcasing superhuman riding, so let’s not let it turn into another FIS event.

How was the crowd in Aspen?

Joey: Funny-looking influencers and lots of fur coats made for a weirdly awesome time (laughs). I hope these events can serve as snowboard reunions in the future.

The invite list was pretty much a who's who of modern halfpipe riders that you travel around the world with all winter. How is it traveling with that crew? The Japanese guys seem super fun to kick it with.

Joey: We are all homies, but the Japanese crew are my dudes! Lately, I’ve kind of gravitated towards that crew a lot.

You went over to Japan last year, right?

Joey: I did, and it was the best trip I’ve ever been on. We went to Aomori Spring Resort, which is where the whole Japanese halfpipe scene is based. There are like 30 absolute rippers that you have never heard of. They're like 14 years old and all so good. Japan is nuts, man. That's one thing I am so grateful for, being introduced to that culture.

Yeah, it’s my favorite place in the world. Didn’t you guys get some really good powder when you're over there, too?

Joey: Yeah, and there was like no one at the resort. There was like absolutely no line all day, every day.

That’s so sick. Where did you head after Snow League?

Joey: I went back over to Laax. There's this dude named Jeremy Carpenter. He's from Iowa. I don't know how he got his start in shaping halfpipes since it’s a super niche career path, but he got contracted to work in Switzerland and posts up at Laax all year. So any time I have between events, I like to go there. It’s so sick. There's a t-bar right next to the pipe, so you can get like 50 laps a day.

Joey Okesson - Laax Switzerland - photo: Mike Dawsy

What's the snow usually like there?

Joey: In March, it softens up a little, and the pipe is super good in the morning. I'll go up with two boards, a pipe board for the morning, and once the pipe gets chewed out, I go free riding. Laax is like a dream; it's my favorite place to go.

Do they have airbags for the pipe out there?

Joey: I think they just got one at Laax.

Do you like using them when you’re learning tricks, or is it weird?

Joey: It depends on the trick. They are very useful, but you can still get broke off on them. Kaishu broke his ankle and was out for the whole year from the airbag. Like, that stuff happens. I like the balance of having both because there are some tricks where I want to feel it out more, and other tricks, like a triple cork, where I need the bag. During the year, I like to ride the pipe, and then when we go to Mount Hood, or Saas Fe in October, it’s like, “Ok, it’s airbag time.”

You are no longer on the US Team, correct?

Joey: I’m no longer on the US Team.

What happened?

Joey: I was on it, and they had a switch-up of management, and some new people came in, fired our head coach, and were just like, “This is our show now”. They're just really into numbers and stuff like that. I always had a weird relationship with the team anyway, even before I got on. I was never on the rookie team. They kind of teased me with that for a while, like, “Oh, I don't know if you're ready”. And then I qualified straight to the pro team, so they had to put me on.

(laughs) Damn that’s one way to do it, straight to pro team.

Joey: Haha, yeah. But nowadays, I still get support from the coaches, and they pay for my lodging and stuff like that. So I have a good deal, you know, it works for me.

It sounds like you have more freedom to kind of do your own thing now.

Joey: Definitely. I love all the people on the team and who are a part of the team. But the dynamic of it all kind of switched up, and that was tough. But that brought me to a new crew, hanging out with Ayumu, Kaishu, Jake Pates, and some others. I get to bounce around a little bit; it's cool.

It’s always good to bounce around with different riders; it keeps it fresh, and you can learn some stuff being around other people instead of the same crew all the time.

Joey: Oh, for sure. This is an experience I've needed, too. Just being away from that whole thing. As we all know, the Olympics can really take the soul out of why we all started to do this in the first place. So, it's been a good experience.

Joey - X-Games 2025 - photo: Isami Kiyooka @isami_kiyooka

Let’s throw it back a bit. Do you remember your first time ever going to a Darkside?

Joey: My first time at a Darkside was at Okemo back in the day. I remember I was kind of scared (laughs). I was like, oh my God, it's hardcore in here, dude.

(laughs)That old shop was all dark and dingy, too. So sick. How old were you?

Joey: I was like 8 or 9, and my mom was like, “Oh, it smells like weed in here.” Looking back on it, the new shop at Okemo is so cool; it looks great, but I loved it when there was just stuff written on all the walls and just the feeling of being in that old shop.

Yeah, I feel like we went through that at the Killington shop when we moved from the original location to where we are now. It took a few years to break it in; it was so bright and clean compared to the old store, but it got there eventually.

Speaking of Okemo, they got the pipe back up!

Joey: Dude, that’s a win for sure!

It was sick seeing you on TV at X-Games with “Save The Okemo Halfpipe” written on your board.

Joey: I had to, bro! They still hadn’t turned it around at that point. I was getting hit up by like news reporters to do interviews about it, crazy.

Is that where you learned how to ride pipe?

Joey: Yeah, I mean, that's like my life right there.

Joey Okesson at 9 Years Old - Okemo, Vermont

You've been riding Okemo since you were a kid. Did you go to Okemo Mountain School?

Joey: I have spent a lot of time at Okemo. I went to this school where they would give us a super long March break, pretty much the whole month, so I started off just going up there and living with a host family for the month. Then started going to OMS when I was probably 11 or 12. My school back home wasn’t really down for me to leave for part of the year, so I eventually got a scholarship and went to Stratton Mountain School for two years. It was a full-year school, but we weren't riding halfpipe, really. So then I went back to Okemo my senior year and kept doing the pipe thing.

Well, you’re killing it, dude, so I think that was a good decision. It’s crazy nowadays if you want to pursue halfpipe in Vermont, your only option is Okemo.

How was X-Games this year?

Joey: X-Games was good. It's always weird going from Laax to that pipe in Aspen because they are so different. It's like the Laax one is the most drawn-out, perfect transition. It's just perfect.

Joey Okesson - X-Games 2025 - photo: X-Games

Are they both 22’s?

Joey: They're both 22, but it makes a big difference on who's shaping it. The Aspen one was a lot better this year because Frank has been working on it for the past two years. But it's usually a little bit of an adjustment.

Is Aspen a tighter transition?

Joey: We always joke that it's like a mini-ramp, but you go so fast that your legs feel like you're on a Mario Cart track. You just like G-out so hard.

What's it like dealing with the crowd and the spectacle that is X-Games? Does it mess with your snowboarding at all or do you feed off that stuff?

Joey: I like riding in front of a crowd; it’s exciting. Especially if the halfipe's not perfect, the energy of the crowd being there helps make everyone ride their best. You just tap into the moment of what's happening.

What was up with that leather jacket? That thing was great.

Joey: My buddy Ed got it for me. He's super into clothes and stuff like that, and he was like, “Dude, I got this jacket for you”. I know when Ed hits me up about some clothes, it’s gonna be dope. He was really hyped on the zipper specifically; he was like, “This is how you know it's a real jacket”.

The Leather Jacket - X-Games 2025 - photo: X-Games

After the event, all I saw online was people talking about the leather jacket. I think it was a good move. It was sick to see you come in with some style like that.

Joey: So, that's another thing with the US Team that can be weird. If you don't have an outerwear sponsor, then you have to wear the team uniform. Now I can wear what I want. I’m not pressured to wear a certain patch or have to make sure I’m showing some hashtag or something. I can run a leather jacket or whatever I want. Straight skate-style.

Do you listen to music during your runs?

Joey: Always.

What’s on the playlist?

Joey: I like rock. I like reggae, too. It depends on the vibe, though. Reggae kind of always goes.

As you sit here in this interview with a Metallica hoodie on. (laughs)

This could be a loaded question, but what direction would you like to see halfpipe go in the future? Keep the progression moving forward or slow down and focus more on style?

Joey: A little bit of both. I mean, at the end of the day, the riders dictate where it goes. That's another weird thing with national teams; they want you to do a certain trick. Look at Ayumu. He can do the sickest air-to-fakiie you've ever seen, but with his regimen and the way he is told to do things, it's just not going to happen. Unless he’s at Snow League, where you have to take eight runs in the competition, and you have to switch it up. I feel like there has to be a balance of both of those things because we (the riders) have been working very hard to push it, but at the same time, you still need to have aspects of snowboarding that make it relatable on some level. If you're just doing double corks on every hit, the average guy is like, what is going on? It all looks the same.

Speaking of air-to-fakies, yours are so sick.

Joey: Thanks, dude. It’s such a fun trick.

Are we switching up grabs or what?

Joey: I like to do Indy nosebone. I ride with Danny Kass a bunch, so it’s sick to try to emulate him a little bit. Japan is really sick, too.

Joey Okesson - Mammoth - photo: Isami Kiyooka

How is it riding with Danny these days?

Joey: It’s sick, dude. He’s such a legend. Being around him has changed my perspective of what it means to be a snowboarder.

He’s another product of the Okemo halfpipe.

Joey: Yeah! He went to OMS. He’s just such a cool dude.

That’s so rad to hear because he did so much for my generation back in the day. And for me personally.

If you were going riding for fun, no judges, no photos or anything, you going 18 or 22?

Joey: 18 all day. It's just fun. It also depends on how well it’s cut.. It's got to be a good 18. But a good 22, just doing big straight airs, is so much fun. It’s just so exhilarating and fast. A normal day of snowboarding with the homies its 18. But now that I've been in this 22 era, it's like when you get those figured out, it’s so fun. I'll just do airs, no grabs, and just land on the deck like skate style.

What's up with rails? You got tricks?

Joey: I got tricks. I got bodied so hard early season this year, actually. And so after that, I was like, dude, I can't be doing this. I was on a directional board and just caught my tail. But yeah, I got some rail tricks for sure.

Are we getting you in the streets at all?

Joey: I was in the streets with my little brother back home during a snowstorm. There's this rail we hit, but other than that, I haven't gotten out there.

Joey Dabbling in the Streets of CT - photo: Laurence Hill

We gotta get you out there next year and get a few clips for the Darkside video.

Joey: I got a board for it, dude. Let's get it.

What's the plan for the future?

Joey: I spent the spring in Switzerland, riding the pipe at Laax, waiting to see if I qualified for World Championships, which was in March. I was right on the cusp, but it came down to one result where I got beat out by .75 of a point, which was pretty fried to begin with. Not taking it personally, but I thought I deserved to be there. Moving forward, making the Olympics is much more important to me than World Champs, so I have my sights set on next season.

We are all rooting for you, dude! Thank you so much for stopping by and catching up. Any last words or thoughts?

Joey: I have a lot of gratitude for everybody who’s shown me love and support in snowboarding & life. I’m thankful to have the support of awesome coaches, Danny Kass & Matt Ladley, and my agency, Lowell Taub & Chandler Hunt. These people make it possible for me to chase my goals & dreams. Shoutout to my mom and little bro, Tommy. Shoutout to my friends all over the world. I’m grateful to share life with so many awesome people!

Joey Airing Over Scott Blum - Loon NH - photo: Spitzer

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