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Images from Skateboarding 2020 Oregon Road Trip for website purposes.

Riding the “Highway in the Sky” with Tom and Trey

Aug 312020

2020 was going to be a massive year for skateboarding. Monster Energy team riders Tom Schaar and Trey Wood were looking at fully stacked schedules, overflowing with skatepark series competitions across the globe and X Games events on different continents. Not to forget skateboarding’s history-making debut as an official Olympic discipline at the Tokyo 2020 summer games.

But then the pandemic hit, and the world went into lockdown.

“I remember coming back from Tampa Pro in early March and learning about COVID-19. Then everything just shut down,” said Trey Wood. “Since then, I haven’t been on a single trip. All there was to do is spend time skating the local parks here in Arizona and hitting the outdoors, going kayaking.”

After weeks of isolating at home, cabin fever became intolerable and Trey began plotting an escape. Road trip with a crew of friends, visiting some of the Pacific Northwest’s most legendary concrete parks? Yes please! 

The squad hit the open road in early August and footage just dropped in an epic skateboard video edit, “Highway in the Sky”. Expect huge airs and high-speed lines under northwestern skies at some of the world’s finest skateparks alongside never-been-done transfers that shut down DIY spots. Watch the three-minute feature now and keep reading for exclusive behind the scenes details from the making of an unforgettable road adventure.


“The whole trip was really Trey’s idea, so thanks to him for making it happen,” said Tom Schaar, who received a group text from his teammate in early June about the mission. Included in the text chain was a crew of close friends that also count among the world’s most lethal destroyers of skatepark terrain: Trey Wood invited Chris Russell, Jake Wooten, Tom Remillard, Clay Kreiner, Skyler King, Chris Gregson, and Klay Andersen, while also arranging to meet Cody Lockwood and Kevin Kowalski once they reached Oregon.


“I just wanted to get things moving again after all this time sitting at home in Arizona,” said Trey Wood, who also enlisted Monster and his board sponsor, Madness Skateboards, for support.


In contrast to the usual perks of traveling to high-profile skate events like the X Games, the concept for this trip was rather down to earth: Pile into a van with the entire crew and head North from San Diego to Oregon, hitting up concrete skateparks along the way. No plush hotel accommodations but perhaps camping here and there under the open sky, plus stopping at legendary Mammoth Lakes concrete wonderland on the way back. 


Turns out, Trey didn’t have to ask twice.


“Everyone was instantly on board!” said Tom Schaar. “This was my first skate trip since the whole pandemic started and I was so bored at home. With not being able to fly, all the contests being canceled and the whole situation here in California getting pretty scary, it was time to get out on the road again.”



The squad got together on August 1 in San Diego for a skate session, followed by a big surprise that started the trip on a high note: With everyone in attendance, Trey Wood’s team manager at Madness Skateboards presented him with his first pro model board. Talk about a major career milestone! 


“Trey had absolutely no idea this was happening, and it got him so fired up. He was killing it the entire trip!” said Tom Schaar. “I was already excited about finally getting out there after being cooped up in our houses, but this got me extra stoked,” said newly minted pro skateboarder Trey Wood.


What also got everyone extra stoked was the list of high-profile skateparks along the route, hallowed ground steeped in decades of skate history. The crew hit Bud Cross Skatepark in Brookings, Buffington Park in Port Orford, and Klamath Falls Skatepark, all designed by Dreamland Skateparks in Oregon. Also invite-only terrain like the concrete bowl in Kevin Kowalski’s backyard in Seal Rock and the indoor vert bowl at skatepark designer Mark ‘Red’ Scott’s house. Plus, a mandatory pilgrimage to legendary Burnside Bridge DIY in Portland and the 40,000 square-foot Volcom Brothers Skate Park in Mammoth Lakes, California, as the grand finale.


“Some of these parks have been around since before I was born. It’s gnarly to think of all the tricks that went down there and finally getting to skate these places was pretty surreal,” said Trey Wood before referencing iconic tricks, immortalized at these parks by the likes of even more iconic pros including John Cardiel. “Burnside was definitely my favorite,” said Trey. “The atmosphere and energy under the bridge are just insane, especially knowing all the history. Watching Cody Lockwood skate there is the most insane thing, he destroys that park.” 


The combination of rich history and unique skatepark design – plus weeks of pent-up energy from pandemic lockdown – provided the perfect recipe for epic sessions. “The whole crew meshed together so well and every single session was sick. Everyone was having a great time and hyped on skating with each other,” said Trey Wood. “A few of us had never been to Oregon and the concrete parks are definitely the best in the world. Everyone killed it and they shut it down at every session!” said Tom Schaar.


Speaking of shutting it down, Tom and Trey made sure to add a few bangers of their own to the Northwestern skatepark legacy (no spoilers!), as seen in “Highway in the Sky”. In order to capture the experience in crisp footage, the crew brought a secret weapon along: Pro skateboarder and filmer Chris Gregson, known for his engaging follow-camera shots on park terrain. 


“He is a wizard behind the camera and when you go out filming with Gregson, you just know it’s going to be special,” said Tom Schaar. “He is really the only one who can do what he does,” said Trey Wood, adding: “I go out filming with him quite a bit because it just looks the best.”



Asked about the trip’s highlights, Tom Schaar is especially stoked on clinching the ender for “Highway in the Sky”, filmed at “a really smooth and great DIY built by Cody Lockwood under a bridge in Portland.” In terms of personal standouts, Trey Wood was quick to name a technical transfer at Mammoth Lakes that took an extra dose of perseverance to lock down. “I kept trying it for so long and finally came back on the last day of our trip and got it a second try,” said Trey Wood while keeping the exact trick under wraps.


Why the secrecy? That’s because, beyond this latest Monster video edit, both Tom Schaar and Trey Wood have been collecting clips for individual video parts, due to drop later this year. “I’m trying to get some more clips under my belt and right now it’s really all about getting as much filming done as I can,” said Trey Wood. 


So with more trips and projects in the works, 2020 may have turned out different than anyone expected, but it’s not a lost year. 


“We’re all waiting for things to get back to normal and contests to start back up. So right now it’s the perfect time to go on some trips to film and get footage,” said Tom Schaar right before rejoining Trey Wood on the next road trip, this time hitting up legendary concrete parks all across Idaho. Here’s to keeping things moving!