"I've been on two wheels since I could walk, just about," he said. "I have probably done a million miles on my bike almost."
The seasoned road warrior is one of hundreds of thousands who returned to Galveston this weekend for the 10th annual Lone Star Rally, but this year everyone seems to notice something different.
"There's a lot of kids out here," Boles said.
"There's a lot of younger kids on the sports bikes and stuff like that," biker Kristin Deschenes said.
It's not them getting older. The biker culture is trending younger, and as some of the old-school bikers will tell you that opens the roads to more inexperience and more accidents on the road.
At least four people died in motorcycle accidents this weekend, including 19-year-old Mathew Taylor. Galveston police say Taylor was speeding the wrong way down Harborside on Saturday when he crashed into a truck head-on. The truck driver involved in the crash was hospitalized, but is recovering and expected to be fine.
"Ride like a granny. No sport riding. No showing off," novice rider Matt Graves suggests.
Graves is fairly new to his bike and admits he's still learning. He came to the Lone Star Rally last year with less than 10 weeks riding experience. We asked him if he felt like he was ready at that point.
"No. To be honest, I don't think I was quite ready. And I had [a girl] on the back of the bike, too," Graves said.
Now more comfortable and confident, Graves and his fellow bikers pass down advice for the new-aged novices.
"It pays to have knowledge and experience before you even decide to hop on the thing," Graves said.
"Pay attention, be observant and be careful," Deschenes said.
The Lone Star Rally wrapped up Sunday night.