The Gambler 500. It’s one of those events that’s hard to put into word.

It’s also one of those events that you go into not knowing exactly what to expect.

You know that teams will be there with $500 cars, all built out with additions like roll cages, shopping carts on the roof, swapped engines, and more. But what you don’t know—and what you’ll quickly learn once you arrive—is that there will be more than 2,000 of these cars, and they’ll be filled with some of the craziest, nicest, and down-for-anything people from all across the U.S. (and Canada!). Think Burning Man meets Mad Max, and then multiply that by 1,000. That’s about as close as I can get to summing up the Oregon Gambler 500.

Taking place in Central Oregon, this year’s Gambler kicked off on July 13^th, and ran through the weekend. There are smaller Gambler events across the country throughout the year, but this is the big show. The main event. The weekend that anyone who really wants to experience a Gambler 500 rally needs to attend.

Which is exactly why my go-to partner in crime when it comes to all things adventure-related, Dustin Keoni, and I decided that this was the Gambler 500 rally we were going to take on. If we were going to do it, we were going to do it right. So, we talked a mechanic friend into also joining our scrappy little team, we started researching cars, and with little to no idea of what we were really about to get into, we started planning our trip.

Our initial thought was to race a Willys Jeep CJ-2A, a car that Dustin was in the process of rebuilding. But, after several issues came up during his engine rebuild, we decided to go with a 2000 Toyota 4Runner instead. Now, here’s where we went wrong—we did not go overboard spray painting, modifying, and tricking out the vehicle in general. A mistake that we quickly regretted when we showed up on day one in Lebanon, Oregon to get the day’s checkpoints.

Because as soon as we showed up to the Gambler 500, we were smacked in the face by some of the coolest, most creative cars we’ve ever seen. Everything from a Corvette C5 where they stripped the chassis down to the frame and custom-built a roll cage, to a rally-ready 1976 Porsche 912E. But there was also the less expected, like a right-side drive postal Jeep from the 1960s and several boats on wheels with engines (really). Not to mention decked out limousines, ambulances, cop cars, and even an old articulated bus.

With our 10 checkpoints for the day finally in hand and a respectable amount of car-envy building up, we were off. We had checkpoint one in sight, which promised a swimming hole, and just like that, our Gambler had begun. We opened the Unpaved app to track our time on unpaved roads, put in our coordinates, and we were officially gambling.

Within 30 minutes of off-roading we linked up with another group of Gamblers, which is what the weekend is all about. Following our new friends, we explored some of the most beautiful backroads you could ever imagine. From hugging steep cliffsides to crossing through forests and over mountains, there was no shortage of scenery to take in during the trip.

Toward the end of day one we set our sights on Big Lake, where an impromptu jump-in was the quickest way to clean off all the dust we had accumulated in our hair, on our clothes—pretty much anywhere dust could go, it went (because who wants to rally with the windows up?). And if I have any piece of advice for anyone new to the Gambler 500, it would be this: do not forget to pack bandanas and dust masks. Just trust me on this one.

Cleaned off and feeling like a whole new team, we decided to call it a day and start to make our way towards Chemult, Oregon, and Gamblertown.

And boy, oh boy, was Gamblertown a sight to see. This is where, inside a 100-acre pumice pit, teams would line up their cars, set up their camps, and make themselves at home for the weekend. And no amount of explaining on my end will get across the chaos, the comradery, the feeling of finding your people, that was found here. So just take my word for it—Gamblertown just might be the best part of the weekend. And that’s saying a lot.

With camp all set up we made our rounds through the pit, checking out even more of the cars, meeting new friends, listening to music at the main stage before eventually turning in for the night. We still had another full day of rallying ahead of us, after all.

The nice thing about the Gambler 50o rally is that since it isn’t a race, you make your own schedule. There’s no 7 am start time. No pressure to get up and hit the trails as quickly as you can. No, the theme here is you make the adventure. The goal of the weekend might be to reach 500 miles in your $500 vehicle, but that’s just a goal. And if you (or your car) doesn’t make it to 500 miles, it doesn’t matter. As long as you had a good time trying, that’s all that does. (And it’s inevitable that you will.)

So, with fresh day two coordinates loaded into our GPS, we hit the back roads once again.

Day two was when we decided to focus on the trail cleanup element—the Gambler 500 is also the world’s largest trail cleanup. And by the end of the weekend Gamblers would fill up more than three 40-yard containers with trash and debris found on the beautiful back trails that they’d been exploring over the previous few days. It’s a great element to the rally.

Day two is also when our $500 car would start to fall apart. We wore through our sway bar bushings from all the off-roading and had to do our best to reposition them so that they didn’t come apart any further. This issue also unfortunately led to us wearing through the steering rack bushings, which meant we had a lot of play in the steering for the rest of the weekend. Other Gamblers would wear through tires, blow fuses, break windshields, kill transmissions, run into plenty of engine issues—this is when the stories really started to get good and the MacGyver fixes ingenious.

Day two ended back at Gamblertown where the bands continued, we checked out even more cars, and teams cracked open the limited-edition Gambler IPAs that were brewed by Conversion Brewing in Lebanon (where we picked up our check points on day one).

And while the morning of day three was when everyone started to clear out, we still had one more thing to cross off our list. And that was attempting a river crossing in a 1969 MG MGB GT with our new friends from Argonaut Garage.

We had heard that two Jeeps from the day before got stuck trying to make the crossing, and we were determined to show them up and be the first to make it. And as the motto of the weekend went, ABG (Always Be Gambling).

With three support vehicles and a plan of action, the MG hurdled itself through the water, making it about half-way before bottoming out on a drain pipe, the tires quickly sinking in the soft mud. Eventually giving into defeat, we towed out the MG, paying our respects to Mother Nature.

We didn’t make it across the river, but we did have an insanely fun time trying with our new friends. And that’s what the Gambler 500 was all about.