
Imagine doing RAGBRAI — riding the entire length of Iowa — on a skateboard. Jeremy Pfaff plans to do just that as he departs on Oct. 5 to head west across the state. If the street skating gods are on his side, he’ll finish his journey in Sioux City around mid-Oct.
Pfaff first discovered skateboarding when he was 10 years old after watching the film Back to the Future in 1985, and got into punk soon after, because the two go together like peanut butter and jelly.
“I’m not that good, but I still enjoy it,” Pfaff said. “Skateboarding is fun. It’s something that you can do by yourself or with people, and it’s a community. You can go to any city in the world with a skateboard, and another skateboarder will come right up to you, and you’ve got an instant friend on the trip.”
The seeds of Skate Across Iowa for Hydrocephalus, Pfaff’s brainchild, were planted after his son Cadogan was diagnosed with the condition when he was four months old. He’s now 4.

“Hydrocephalus is excess fluid in the head that expands the ventricles and causes pressure on the brain,” Pfaff explained, “and untreated, it can be fatal, but there’s a lot of things they can do to remedy it. My son has a shunt, which helps drain the cerebral fluid, so it relieves the pressure. He’s been surgery free for over three years, but he had three brain surgeries before his first birthday.”
The father and son share a Sept. 25 birthday, which makes the project extra special when the newly minted 49-year-old kicks off in Davenport. The journey is scheduled to start following a benefit show at The Dark Slide skate shop in Des Moines, which will feature some of the bands who have donated tracks to a Bandcamp compilation album also supporting Pfaff’s cause.
Anthony Jackson — the drummer for River City Rejects, a street punk band from Omaha, Nebraska — helped put together the comp after he saw some of Pfaff’s social media posts about the trip.
“Being a father of an 11-year-old and a 9-year-old, I would do just about anything in my power to help another family,” Jackson told me. “I immediately sent Jeremy one of our tracks and asked a handful of other bands to contribute to the compilation that Jeremy was putting together. But it wasn’t until I met Jeremy in person at one of our shows that I finally understood how important this compilation is.”
Even though skaters and punks get caricatured as antisocial misanthropes, these subcultures tend to be as community-minded as a Kiwanis Club, if not more.
“Skateboarders and punk rockers are really the people that will come together the quickest and without a care about anything else and give what they can,” Pfaff said. “A couple of the bands gave me unreleased material, and another band recorded an exclusive song that hasn’t been released anywhere else.”
To plan the route, Pfaff used the “walk” option on Google Maps to figure out how to get from town to town. “The roads are pretty rough, but this company Loaded Boards sent me a skateboard that has these large, soft wheels that I’ve taken through some gravel and some rough areas already, and they seem to handle it perfectly,” he said.

This ambitious project hasn’t been without its obstacles. Pfaff launched a fundraiser to help pay for transporting the heavier items that he needed, but didn’t secure enough money in time.“ So, I’ve changed what I’m taking … to travel as lightly as possible,” Pfaff said. “Hopefully the fundraiser gets enough so that I actually have money to stay in hotels or motels and get something to eat each day.”
Still, he has been overwhelmed by the support from the skateboarding community, in the U.S. and abroad. Like from Skullen Skates, a family-run business based on a small island in the United Kingdom. Skullen Skates’ Danny Butcher designed the logo for Skate Across Iowa for Hydrocephalus — a character that was nicknamed “Cornelius” after it was suggested by his social media followers.
“I asked if anybody would be willing to donate and help me with the artwork, and Danny jumped right in.”
“Etnies, a bigger skateboard company, also has sponsored me with a lot of product,” Pfaff continued. “They were completely down, which was a little surprising to me. I reached out to them, hoping but not expecting anything, but they were right there, ready to go. That just goes to show how skateboarding is the glue that holds us together, because we support each other.”
Kembrew McLeod grew up surrounded by skateboarders in Virginia Beach, but his skills on the deck are pretty whack.
Editors note: This article has been updated since its original publication in Little Village’s October 2024 issue to reflect the delayed timeline of Pfaff’s journey.
Related event
Skate across Iowa for Hydrocephalus benefit show
The Dark Slide | Thursday, Oct. 3, 7:30 p.m.
Hosted by John Waugh and The Dark Slide, with live music and open slots for interested bands. All proceeds go to supporting Hydrocephalus research.


