A helmet sits July 19, 2024, on top of one of the many motorcycles around Roy Raley Park in Pendleton for Pendleton Bike Week.

PENDLETON — In mid-July, Pendleton Bike Week brings bikers and tourists alike to Pendleton, filling the hotels to the brim. Other bikers drive over in motor homes or campers, making sure their bikes stay pristine and show-ready.

Just a few miles away, however, Kelly McCleary is setting up his tent, portable stove and bike in a nearby park.

“I’m a minimalist and pretty simple, I just pack a small stove and tent and drive over on my bike,” McCleary said.

The biker said this comes from his three years as a soldier in the U.S. Army, where he was stationed at Fort-Lewis Mcchord in Tacoma.

Since 2015, the first year of Pendleton Bike Week, McCleary and his 2015 Indian Chief Classic motorcycle have not only been attending but been the first ones there as well. McCleary arrives as the first biker each year on Wednesday morning, a full day before the festivities even start.

Although McCleary has had the bike for almost nine years, 11 others have been under his ownership since his first bike when he was 15 years old. McCleary has been riding for 55 years, but his love kick-started at the age of 4.

“My mom took me to the bank back home in Gresham, and there was this bike parked up front,” McCleary said. “I stayed outside and watched it, and the owner of it was this big guy with greasy boots, Levi’s and a leather jacket. He walked up, looked at me, smiled and gave me a salute and took off, I’ve been hooked ever since.”

The Indian Chief Classic ranks as McClearys favorite bike he has owned, even though he bought it sight unseen on eBay. The bike originally resided in North Carolina, but with a $1,000 veteran discount and $1,500 of accessories, McCleary wasted no time shipping it across the country.

McCleary has traveled far and wide with his motorcycle, to places much further than Pendleton.

The biggest motorcycle rally in the world resides in Sturgis, South Dakota, which McCleary has attended four times now, starting in 1991. While the annual Pendleton event brings in up to a couple thousand, the Sturgis Motorcycle Rally attracts 500,000 on average, and up to a million on some years.

With decades of riding experience, the community is what keeps McCleary coming back.

“The best thing about this is interacting with other bikers. You can come here by yourself as a total stranger and make friends all around,” McCleary said. “It’s a culture, community and a brotherhood.”