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Then, the pandemic hit. Due to travel restrictions, Caruso and his cousin couldn’t take on the challenge.

Instead, Caruso considered the United States could be another valid option.

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“A year or two years past, I just kept thinking about it,” he said. “The idea never left my head, and then it just kind of kept evolving.”

And years later, he made that dream a reality.

The Journey

Caruso planned to start his journey in Venice Beach, California, to begin in a warm climate. He would then travel east as, the weather grew hotter, ultimately ending in Virginia Beach.

He also mapped out his entire route ahead of time, looking up common paths that people had done previously and the weather.

The YouTuber downloaded the app Caboose, which maps out trails and roads that are cement. Caruso also vlogged, or to filmed, a video each day, documenting his entire adventure.

On a typical day of the journey, Caruso would wake up at 5 a.m. He would then “instantly” grab his phone and edit a video recorded the night before.

At about 7 a.m., he would hit the road, skating more than 50 miles per day.

While his route is pre-determined, other details were spontaneous.

“I have nothing planned,” Caruso told Patch as he skated through Texas. “I just kind of will be like okay, I’m heading to this town. Let me look at the map for tomorrow. And then I’ll go on Google and see where there are hotels and just figure it out.”

Leaving room for impromptu decisions, he said, such as meeting new people, is what made the trip special.

“That’s one of the main reasons I did the trip,” he said, “I just love meeting people. When you’re traveling alone, you can lend yourself to more interactions.”

Caruso would meet new people each day. Some would learn on the spot about his journey, while some had watched every YouTube video.

He received not only the gifts of conversation, but gifts ranging from sandwiches to a civil war bullet.

Of course, challenges occur. Being on one’s feet for so long and outside, sneakers tear, the weather always changes.

Caruso recalled one of his biggest obstacles at the beginning of his journey.

“There was one climb from Palm Springs to Joshua Tree that was just gigantic. Just huge,” he said. “Now my legs are just conditioned, and I don’t even really think about it. But in the beginning, I was sore and exhausted.”

Six years sober, Caruso decided to donate 25 percent of his gained profits to Natural High, a drug prevention nonprofit that inspires and empowers youth to find their natural high and develop the skills and courage to live life well. The rest of the money will cover food, hotels, and other expenses on throughout this two-month long trip.

YouTube Career

This is not the first time Caruso expedited a skateboarding challenge.

In 2019, he traveled to all 50 states, learning a new skateboarding trick in each one. Caruso also spent time skating in Central and South America, and recently spent a month in Moldova with the nonprofit Skate Aid, teaching Ukrainian refugee children to skateboard.

“They basically had never even seen a skateboard before. Everyone just loved it,” he said. ” Every day they were excited. When I’d show up, they’d (the kids) be waiting there for me.”

He also traveled to Ukraine to connect with other skateboarders and to see first hand the reality of the war.

“It was amazing. It was the same kind of energy, all the people, all the skateboarders — they were still in such good spirits,” he said. “It just shows it is important, having a little community and something to focus on day to day.”

Utilizing skateboarding as a beneficial activity for children is a universal and personal truth, he said.

Long Island Influence

Living in Lindenhurst, Caruso learned how to skateboard at age 14 with friends after school. Growing up, he also watched his older brother skateboard.

Caruso and his friends often skated at the Lindenhurst gazebo.

“We would always get kicked out,” he said.

In 2004, He and his friends then petitioned and were successful instating Tanner Skate Park.

Caruso continues to advocate for skateboarding in his hometown. This year, he fought for its renovations this year and to have the village create a new cement park. Every September, he also hosts “Tanner Skate Gym,” in addition to multiple skateboarding contests throughout Long Island.

Skateboarding is important, Caruso said, because it makes people feel “free” and is like a “meditation” — a healthy feeling and skill that can benefit everyone.

“It just brings you into the present moment. You have to be so focused while you’re doing it, like the physical challenges, then the mental challenges,” he said. It’s so detailed, and you have to be so balanced in trying a trick hundreds of times over and over. Things you’re just absorbed in the present moment.”

The Finish Line

On Day 57 — the final day of the challenge — droves of people lined up to watch or skate alongside Caruso.

Early in the day, a family stood outside their house to catch a glimpse of him.

“I wanted my son and nephew to meet you to let them know that anything is possible,” said a man in the family, on Caruso’s vlog.

The father and teen son tagged alongside the Long Islander on a bike and skateboard. The three ride together for a few minutes before parting.

They stopped at a gas station to say goodbye.

“I lost four friends to addiction this past year,” the father confesses to Caruso, showing his support for the cause. “It’s been a hard year for me.”

The amount of similar encounters only grows throughout the day. Caruso interacts with a cornucopia of individuals, from a police escort over Virginia Beach’s Jordan Bridge, cars who honk and cheer him on, a short pit-stop with a skate store owner, to riding along with a golf cart driver.

Everyone who sees Caruso emotes pure inspiration, joy, and fascination. Due to his amicable energy, strangers continue to be vulnerable, sharing secrets.

A longboarder admits she suffered a back injury, and confides to Caruso that skating was one of the few things she could physically do that cleared her head.

As Caruso reaches the water, the crowd grows to hundreds, carrying signs. Observers cheer as he skates through the boardwalk, like celebrating a hero coming home.

When he reaches the sand, the skateboard is thrown to the side. Caruso sprints to the water, jumping in without inhibition.

“Unreal, honestly,” he told reporters on how it felt to reach Virginia Beach only moments after emerging from the ocean. “I was not expecting this many people.”

Bobby Dyer, mayor of Virginia Beach, later proclaimed May 19 Chad Caruso Day in an official ceremony. He also announced that Caruso was nominated for a Guinness World Record for the Fastest Cross Country Journey of America on a Manually Powered Skateboard.

At the end of his vlog, Caruso told viewers that the whole day had left him with gratitude and without words

“To see it all at the end, it really left me speechless,” he said.

What’s next, Caruso doesn’t know. But for now, he’s accomplishing another dream.

“I’m going to Italy with my girlfriend,” he said.

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