‘Sturgis meets Burning Man:’ Gambler 500 celebrates in Redmond for its 10th year

Published 1:13 pm Friday, July 14, 2023

About five years ago, Thomas Laird was passing through the city of Lebanon when his interest was piqued by a group of “crazy cars” passing by. Too curious to move on with his day, Laird asked the drivers where they were headed. They told him they were going to the Gambler 500.

Laird, now 35, says he was “kind of hooked at that point” and after looking more into the event, which had started in 2014 as an off-road race from the Portland area to Central Oregon using cars that were built for less than $500. The first year included a group of about 20 friends. Now, 10 years later, about 5,000 people will participate in the 2023 Gambler, based at the Deschutes County Fair Grounds and Expo Center. Laird himself has leveled up, converting an old station wagon into a cool ride that stands out among the crowd.

The event ran from July 14-16 with admission at $40 for people 21 and older and $20 for anyone under 21. Overnight vehicle admission without a trailer was $80 and with a trailer or RV was $150. Tickets included access to overnight camping, HooptieX racing and Gamblertown, an area with live music, merchandise and vendors handing out free items.

“Look at the complete chaos,” Laird said on Friday, surrounded by wildly painted and loud contraptions rumbling around the fair grounds. “It’s like Sturgis meets Burning Man. Yeah, and it’s just super Oregonian. The creations that guys in their back yards think of with a welder and a couple cases of beer — it’s amazing.”

Tate Morgan, creator of the Gambler 500, realized as the event gained in popularity it would negatively impact on the environment and public lands if it continued. So they scrapped the off-road race idea and reimagined the purpose of the gathering. Instead of a race, the Gambler 500 has become a challenge to pick up as much trash off public lands as possible. Organizers created the nonprofit Sons of Smokey, as well as an app that points participants to a map with trash sites filled with old car parts, boats and other debris.

“It’s important that the Gambler 500 exists,” said music organizer Shane Brown. “There’s simply no resources available to gather, clean and remove as much trash as we do on an annual basis.”

Brown became involved with the Gambler 500 after seeing a few Youtube videos about it. An artist and musician, he got in touch with Morgan and was offered a position.

For seven years, Brown had organized the music that blasts through the campground. He also designs and creates sets for the performances, with the goal each year of “increasing our badassness presence by 40 percent.”

Original Gambler, and Morgan’s old college roommate Chuck Brazer, is in charge of the HooptieX races. Participants signed up to race around the track in their barely-held together jalopies. Over the last 10 years, Brazer said he has watched a community form around the Gambler, with familiar faces coming back year after year.

“If you break your car, there’s an army of people out there to fix it,” Brazer said. “We get you back on course.

It’s been made really welcoming to a beginner. It’s a community aspect and everybody is extremely helpful.”

Father and son duo from Portland, Dean Lukowicz, 56, and Oliver Luedtke, 15, found themselves shopping for an old, beat up 1986 Mustang back in April after Luedtke saw a Youtube video about the Gambler in late December.

As first time participants, they’re excited to off road and pick up as much trash as possible.

“We poured a lot of blood, sweat and tears into it,” Lukowicz said. “We just hope it makes it back home.”

Last year, 426,000 pounds of trash was collected off public lands by Gambler participants. This year, Morgan hopes to beat that record.

“There’s this groundswell of people that are aligned with us,” Morgan said. “I didn’t educate these people or make them care about it, they just like the cars, people and the environment. So we just kind of gave them a name and a place to all gather.”