By Alex Spadacenta ’17

Headphones in his ears, one hand in his pocket and a skateboard in the other: James Bowles ’18 is ready to ride.

He grinds on a bench next to the Westport Library, where skaters have been stripping the paint off its smooth surface for years, according to Max Dupont ’18. Bowles and Dupont add to those scrapes almost everyday after school.

For Bowles, skateboarding has been a staple in his life since the second grade, where he first picked up his board in an effort to overcome his OCD.  

“Whenever I was skating, I was not really focused on [the OCD], I wasn’t dwelling on anything so I think skating’s been a good way to clear my head,” Bowles said.  

Obtaining new skills is part of skateboarding, however, even the simplest trick can be a major struggle to master. As a kid, Dupont said it was painful to fall, but now the adrenaline rush from falling pushes Dupont to work even harder. “You go through all that pain and once you get it, it just feels so good to finally get that trick you’ve been working for, and just ride away.”  

Bowles and Dupont began to swerve in and out of Main Street’s staircases and hidden alleyways, since the Compo Beach Skatepark is rarely open. In fact, in 2014 the town was contemplating destroying the park during beach renovations. However, Bowles would not stand for destroying the park where he learned to skate.

“I brought a few friends together and I went to different town hall meetings and we spoke about it, and wrote a letter to Dan Woog and a bunch of other people,” Bowles said. Due to Bowles’ and his friends’ efforts, the town ended up keeping the park where Bowles has served as a CIT during summer camp. According to Daniel DeVito, the Westport Parks and Rec Operations Supervisor, the skatepark is currently in the Compo Beach Proposal Plan.

As time passed, Bowles and Dupont grew tired of the quiet streets of Westport and found themselves venturing into Manhattan almost every weekend.

“Skateboarding is like art to me. When you’re in the City and look back and see all your friends and all the big buildings, it just looks so cool,” Dupont said as Bowles nodded in agreement.

In the City the boys take part in “street skating” where they complete tricks on stairs, cones and benches on the sidewalk. From Tompkins Square Park, to the Courthouse Drop, to LES skatepark under the Manhattan Bridge, to Brooklyn, the boys have discovered skateboarding is not just a hobby, it’s a community.  

Skateboarding skyrocketed in the 1980s when skate competitions arose. Since then, the community has grown. And in 2006 when the famous skateboarder Harold Hunter passed away, the entire community came together, and still do, to honor him.

“It’s amazing how much people cared and how much they would do. It’s a skate community. The skate community is probably the most unique community ever,” Dupont said.

“I’ve met a lot of cool people through skateboarding,” Bowles said. One of his best friends is a 39 year old man named Eddie, who taught Bowles how to skate at a young age.

Jasper Fowle ’18, a fellow boarder, actually met Bowles through skateboarding, and has been opened to a whole new group of people. “The other day I was walking down the street in New York and I had holes in my shoes in the exact spot skaters always have holes, and a guy walking past me called out and asked if I skated,” he said.

The communal aspect of skateboarding in combination with the art has converted what could have been considered just a sport or a hobby into a culture.

“Style is everything in skateboarding now,” Dupont said. Skateboarding companies like Supreme and Thrasher have come out with numerous stickers and other items of clothing to suit the riders. Vintage Tommy Hilfiger jackets and clothes are making a comeback, and boarders will go to the deep ends of second-hand shops just to find that perfect look. Not only are clothes stylish, but transparent grip tape, the usually black tape on the boards, is very “trendy” as Dupont put it.

But skating is more than a style. “At skateparks, you feel at home,” he said.

“In skateboarding everyone is just a skateboarder. Nobody really cares about race or orientation or socioeconomic status,” Bowles said. “When you’re out skating with friends, you’re all equals.”