July 25
Roll The Bones: Gambler 500
Words and photos by Chris Nelson
The annual Gambler 500 O.G. in central Oregon was wonderfully strange to behold. An absurdly dusty, drenchingly sweaty, dystopian fever dream- like Mad Max meets Burning Man—but at its core, it’s an easygoing group of a few thousand goodhearted people having wonderfully pointless fun in hilariously horrendous cars.
A decade and a half ago in central Oregon, a group of friends and automotive misfits started buying unloved, ill-running, beat-to-shit commuter cars for $500 each. They then painted those cars stupidly— with winged dicks, Meow Mix sponsorship stickers, or phrases like “Pavement is Lava”— and then drove them down rutted off-road trails deep into the wilderness of the Pacific Northwest to drink whiskey and camp for the night. As they made their way back toward civilization, they cleaned up trash from the trail and started combing through Craigslist ads, looking for replacement parts for whatever broke on their shitboxes that weekend.
The original “O.G” gathering happened in 2014. Thirteen flamboyantly decorated jalopies showed up for the off-road navigational rally that wandered through forest roads, over the mountains, and into the desert. Attendance doubled the next year, and then a video of the Gambler 500 went viral, and the event captured the attention and imaginations of thousands of off-beat automotive enthusiasts who understood the importance of inexpensive and inclusive fun.
In 2017, I first met the figurehead of the automotive circus sideshow that has brought me so much joy and so many unbelievable memories, Tate Morgan. At the Portland International Airport, he picked up me and the late Jessi Combs— the fastest woman in the world who once described the Gambler 500 as “a wild mob of fun havers and good doers”— in a short, yellow school bus with the name of a little league baseball team written in big black letters on the side: Muddawgz. He brought us a pair of de-governed and rattlecanned, six-horsepower mini-bikes to race in the 100-mile “Mini Moto Enduro,” which Jessi obviously won.
The next year I traveled to Iceland during endless summer with Tate and a good group of fellow idiotic automotive adventurers to ride mini-bikes across the lava rock of vast, black volcanic highlands. It was magical and not nearly as dusty as the 2025 “O.G” gathering, but perhaps to some that is part of the appeal of going to Gamblertown, where you’ll meet just as many weirdos as you would at the Sturgis Motorcycle Rally or the Gathering of the Juggalos, but they tend to be less creepy and more charming.
Gamblertown is a massive three-day, pop-up camp of tents and vans that is rustically post-apocalyptic and vibrantly raucous. Good barbecue is being served up, go-karts are racing around a dirt track, live music is playing late into the night, and friendly hooligans are encouraging you to take a swig from a bottle of whiskey, or if you’re brave enough jump their pull-start minibike over a five-foot-tall fire.
"There is no goal in the Gambler, because you get out what you put into it," says Tate. “We didn't want to put any real rules or boundaries in place, apart from ‘don't be a dick’ so if you're looking for structure, this is not for you. You can only ‘win’ by being the coolest or most helpful person, and picking up the most trash off of public land.”
While responsible stewardship of our public lands has been part of the Gambler 500 since its inception, trail clean-up efforts are becoming more focused and more impactful, and over the past several years Gambler 500 participants have removed millions of pounds of trash from public lands.
At this summer’s O.G. gathering, with the support of an affiliated non-profit organization called Sons of Smokey, Gamblers removed 200,000 pounds of trash from public lands around Madras, Oregon, including 15 abandoned cars, 12 discarded RVs, and a dumped boat. Tate says, “We chose this area to do a total reset, knowing there would be about half the trash as last year’s O.G. This was about spreading out and taking the time to really deep clean one area to prevent it from getting trashed again.”
This is a community that respects the lands that we live on and celebrates the life that we share, and they have a very funny way of showing it. If you are into freedom of automotive expression, responsible exploration, and unadulterated fun, then maybe you need to buy a shitty car and go Gambling.
Jul 25
Pioneer Stories: Brendan Byrne - Through the Lens of a Modern Nomad
Jul 25
