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The Gambler 500 Is the Badass Off-Road Rally You’ve Never Heard Of

If I told you there was a secret off-road rally race where participants gas up the cheapest, most impractical, piece-of-junk cars and set off on a navigational backroad adventure in the middle of nowhere, you might think, “OK, dude, lay off the absinthe.” But this wild underground race is real.

It’s called The Gambler 500 Rally and it takes place in Oregon.

Gambler 500/Facebook

The Manual first heard about The Gambler 500 from an unnamed CEO who was gearing up to partake in the insane adventure, where he and his COO would be in a beat-up car cruising backroad tracks (we use the word “road” loosely) without any cell service. Needless to say, our interest was piqued.

How it works: Participants are encouraged to spend no more than $500 on a vehicle to drive during The Gambler. This limit is not enforced or officially verified, but abided by — the point of Gambler is not to win. It’s about finding new backroads all across Oregon and piloting your beater over 500 miles.

Think Mad Max but with friendlier drivers.

Presented by Sig Sauer, The Gambler 500 began as a simple weekend game between close friends in 2014. Eventually, they decided to let the world in and allow more people to join the fun without expanding to the point of dirtying up the natural Oregon landscape. Because yes, The Gambler 500 will have you driving through sand and mountain. This past year, The Gambler’s popularity led to the expansion of a new basecamp, where attendees meet up to start and end their 500-mile loops — oh, and come a few days early, park their camper trailers, and party with live music, barbecue, and minibike excursions.

Participants from California, Idaho, Oregon, and even New York come with fun, cheap vehicles, while others bring off-road and overland rigs to participate as assist cars for those who break down along the way.

The Gambler 500 technically starts when you hit the gas. Before starting, they recommend you use navigational apps capable of downloading offline areas you plan to travel. Which leads us to our second preparation trip: plan your route ahead of time.

Once you hit the pedal to the metal, log your progress and see your ranking with the Unpaved Challenge (UNPVD) app. For GPS-enabled iPhones and iPads (the app doesn’t work well with Android devices), download UNPVD and hit go before starting. The app will run in the background while you’re off-roading and track the percentage of unpaved travel you complete. If you’re outside of Oregon and traveling to The Gambler 500 from far away, start the app en-route to Oregon and select routes that increase your unpaved travel. This increases your percentage of land covered and therefore your ranking. There are are also several public start areas to meet up with friends.


Those new to the adventure should study some of the waypoints from the previous years for inspiration. And of course, drive save, respect the land, and try to pick up trash along the way. Post Instagram pictures of the abandoned couches, mattresses, and whatver else you help clean up, tagging @thegambler500 with hashtag #sonsofsmokey to win awards provided by Yakima and Benchmade Knife Company.

Once you’re back at camp, share stories among new friends as the “Scepter” is awarded to the team that most embodied the spirit of the Gambler. Awards are also given to the team with the longest trip, most RC-looking vehicle, most tactical, most impractical, the “Recovery Hero,” and more.

Other sponsors for the event include JC Whitney, Interco Tire, SuperWinch, EmWest Motorsports, Heatwave Visual, RhinoLinings, TrailworthFab, Total Chaos, MC Custom Fab, Pabst, ICON, Coleman Powersports, Canyon Coolers, and AutoPartsWarehouse.

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Jahla Seppanen
Former Digital Trends Contributor
Born and raised off-the-grid in New Mexico, Jahla Seppanen is currently a sports, fitness, spirits, and culture writer in…
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