We’ve always had an affinity for the Gambler 500. Shopmonkey and the Gambler 500 might be lesser known, but those who know us, love us. And when it comes to custom builds, extreme car repair, and fun car culture coupled with a sustainable purpose—we’re made for each other.
Gambler 500 is a grassroots car rally that kicked off in 2014 with the purpose of removing millions of pounds of trash from forests every year. Cars, refrigerators, couches—Gamblers get it all.
Tate Morgan, Gambler’s founder, started driving with a few friends that first year. They took some $500 junk cars on an off-road rally that spanned hundreds of miles through the woods. Geared up with compasses and maps, they “gambled” on whether or not their cars would make it to the finish line.
Fast forward 9 years, this last Gambler 500 hosted 8,000 participants in their annual event at Redmond, OR. Other Gamblers have popped up all over the U.S. and spread to Canada, Mexico, and even Iceland, each one embodying that same spirit of adventure as the first—$500 junkers only, no navigational tech, and pick up the trash.
“What I am gracious about is that everyone comes out and has a great time and seems to understand the humble beginnings, now 10 years ago, that started this event. A small group of tight friends spending time out in the woods together. It doesn’t cost anything to use public land and throw some waypoints out in the forest and have some fun.
This event proves that you can keep things cheap and fun. A bunch of awesome stuff happens for public spaces, measured in pounds and acres. If you were to measure what we accomplished over the last weekend in dollars—if you were to try and activate and pay thousands of people to clean up trash over the hundreds of thousands of acres we covered this weekend, it would be a multi-million dollar affair. This, along with amazing memories, is the spirit that we can carry on.”
— Tate Morgan, founder of Gambler 500
The Low-Down
Driving down a long dirt road at the Deschutes County Fairgrounds, you cruise past a sign that says “Pavement is Lava.” You know right away—the culture Tate instilled in Gambler back in 2014 runs deep. For anyone who goes, there are two rules:
1) Pick up trash.
2) Don’t be a d*ck.
The Gambler 500 isn’t just an annual rally. It kicks off a year-long stewardship effort to clean up rustic areas. Tate and his team developed an app and 501(c)(3) non-profit organization called Sons of Smokey, which supports their record-breaking effort for being the “largest trail cleanup in the world”—we’re talking 180+ yards of debris!
“The app is free and easy to use. If you find trash out in the woods, something that you cannot take with you—it could be a couch, abandoned vehicle, bags of trash, etc. that is not supposed to be there—you can open up the app. Do the long pause to tag the location, take a picture, and leave a description. This uploads it to all users on Sons of Smokey, including off-road organizations, government agencies, etc., who can find it and direct the clean-up efforts to it.”
— Tate Morgan
Beyond sustainability, sticking to dirt trails and driving deep into woods, grasslands, and deserts is part of the fun. Many Gamblers from the Pacific Northwest take it one step further, getting there and back in their junkers without taking freeways.
Although the Gambler isn’t a race, there is competition. Gamblers with true “$500 vehicles” have a shot at winning the annual saber. This coveted award goes to the Gambler who picked up the most trash and covered the most ground during the two-day event. (There are designated waypoints along the route to check-in and a mid-way point to offload trash.)
Modern vehicles are welcome to participate too. Tate drives a newer Ford Bronco. There are modern Jeep Wranglers, and we even spotted a Rivian R1T at this year’s event!
The Event
If we’re describing the Gambler to someone who’s never been, we’d say it’s the world’s largest trash cleanup in the U.S. and a car enthusiast’s haven.
This year, Shopmonkey got in on the action. Sponsoring the official food and beer tent for the two-day event, we gave away Boneyard beer and grilled hot dogs for everyone. It was a scorching weekend, with temps reaching over 100 degrees on Saturday, so many Gamblers savored a cold brew and some shade.
When you get to Gamblertown, the event’s base camp, it feels like a post-apocalyptic world. Think Madmax meets Burning Man. You quickly realize that this is special—an environment where you’re welcomed with open arms, regardless of vehicle, politics, or attire.
Gambler junkers come from all over, sporting a wide range of build quality. Backyard garage hacks are definitely in the spirit of the event. You’ll also see a handful of pretty amazing proper builds, inspired by crazy ideas and executed by some of the most talented auto shops and techs in the country.
We chatted with Gambler Austin Nichols from Small Car Performance in Fife, WA. Austin and his co-owner and wife Michelle build custom off-road solutions and conversion kits for Vanagons, buses, and more. You can easily see why they fit right in at the Gambler. They’ve also used Shopmonkey since starting their business in 2021 because it’s the only platform on the market capable of .
“I used to spend an hour or more putting together a quote for our custom builds in Excel, and with canned services in Shopmonkey, I can do it in less than 10 minutes. Our work is so complex that we initially had a very difficult time finding a service writer who could manage our builds. Now with Shopmonkey, I can write service myself and still have time to work on the business each day.”
— Austin Nichols, co-owner of Small Car Performance
Austin’s enthusiasm for the Gambler stems from the people and what he’s dubbed “the most fun he has ever had in a Vanagon.” This is one of those melting pots where it’s easy to find connections with like-minded automotive enthusiasts. As a third-year participant, he keeps coming back to go off-roading, hang out at Gamblertown, and make friends who share his passion for vans.
At our core, Shopmonkey’s purpose is to . And that purpose stems from our passion to connect equally passionate car owners with the shops supporting their driving adventures.
And those adventures are plentiful, especially out on the trails. “It's an adult playground out there and the deeper into the mountains you go, the cooler it gets, both in views of the central Oregon landscape and in temperature,” said Nick, one of two Gamblers sitting on the roof of a Crown Victoria cop car while plotting out his next route on a map and compass. When we asked this group how many miles had logged so far, they reported over 50 in the mid-afternoon Saturday.
We also saw several cars being towed back into Gamblertown after suffering mechanical issues. If it can’t be fixed on the trail, chances are there is another Gambler nearby who can fix it for you or tow you back into town. There are endless situations of technicians providing a helping hand. This is what we love, a melting pot of car lovers, fueling each other's passion for driving and keeping cars on the trails!
The Off-Road Ahead
What Austin describes—the camaraderie, the passion for clever builds and car repair, and the welcoming, non-judgmental atmosphere—it’s everywhere at Gambler 500. This unique subculture of car ownership connects people who share a like-minded passion and purpose for the outdoors and cars.
If this sounds right up your alley, you can find a local event or, guess what—anyone can start a Gambler, and even license the Gambler name and logo from Tate for free. All you have to do is follow these simple guidelines:
1) Keep it free.
2) Keep it fun.
3) Keep it clean.
With this mantra, hundreds of local Gambler events hit the road year-round. To learn more, check out Sonsofsmokey.com.
We were pumped to be along for the ride this year, keeping Gamblers refreshed and fed, and supporting the culture Tate and his crew have cultivated. So, what’s up next?
First and foremost, we want in! Next year, we’re planning a build of our own and you can too!
Take on more custom builds with a software solution like Shopmonkey
Dig deeper into the Sons of Smokey and Gambler 500
Learn more about Shopmonkey’s work with other shops in the industry.
Whatever piques your curiosity, reach out to us. We’d love to chat!
