Hitchhiking The Gambler 500

Story and Photos by Justin Moore

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The trees and signs blurred by as the dark green Crown Vic made its way down Oregon’s Columbia River Gorge. Every time the car changed lanes I had to brace myself from sliding to the other seat since tit had clearly been a decommissioned K-9 police cruiser which means that there are zero seat belts in the back. Sitting directly in front of me is a curly haired metal worker, interior designer, gravity bike enthusiast, and custom knife maker named Harlan Whitman (instagram.com/ooakforge). Harlan is very focused on his driving but still eating yogurt covered pretzels while making his way down “Oregon’s Autobahn” as he so affectionately calls the long stretching corridor from Portland to Hood River that’s sandwiched between massive sheer cliff faces and one of the largest waterways in the country.  His navigator, Brodie McNabb is more relaxed and enjoying the scenery while telling jokes and keeping a watchful eye on the traffic situation through a bug-splattered windshield emblazoned with the number 216 on the upper passenger side.

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What sort of madness would have to develop in order for this to play out? How in the world does someone put themselves (willingly) into this situation? This is the Gambler 500. What started out as a bunch of friends fixing up old neglected vehicles has turned into the first major sporting event created by social media. Not a race at all, Gamblers scramble to way-points on public land. Usually an illegal garbage pit or high school party spot. Once there, part of the objective of the “overland adventure rally” is to pack out the most garbage, debris, or rubbish that they can carry. Prizes are often awarded for bringing the most weight in waste back with you. All the normal rules of the road apply and it’s free to enter. The only general rule of thumb is that the car should be around $500 and the more impractical the better.

Gamblers at the start of the event, taking the theme of their hooptie very seriously.

Gamblers at the start of the event, taking the theme of their hooptie very seriously.

As we make our way into Hood River and take note of all the casual drivers that pull over to get out of your way when driving a former police cruiser (then get really upset to know that they just made way for a car full of dirtbags), we prepare for the gravel roads that lay ahead in Mt. Hood National Forest. The cruiser maneuvers the terrain elegantly and the ride is smooth over intermittent pavement on the single lane roads weaving into the denser forest as we gain elevation quickly.

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Tate Morgan looked at me like I was crazy. “No, really. I just want you to hold this light so I can take your photo”, I reassured him. It was late, close to 10 and we were still feverishly modifying cars. The entire garage smelt like krylon, exhaust, and fresh welding. We had to be at the start of the event at 4am the next morning and there was still a lot to do but people were showing up out of nowhere to help. The man that all the Gamblers affectionately refer to as “The Godfather”, Morgan is a lean 37-year-old father of two who spends as much time in the great outdoors as possible. His disdain for rules and order clearly show through with the first two guidelines of the Gambler 500 being “Fun>Rules” and “Don’t be a dick”. Both of which can be seen stickered and painted over many of the contestant’s vehicles.

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Monster Industries, (  monsterindustries.ca )  a Canadian construction and maintenance company, used the Gambler 500 as a corporate retreat. They bought matching Corollas and came in a day before the race to modify each to their own style.

Monster Industries, (monsterindustries.ca) a Canadian construction and maintenance company, used the Gambler 500 as a corporate retreat. They bought matching Corollas and came in a day before the race to modify each to their own style.

Tate takes his responsibilities of running the Gambler seriously, and now with it being in 26 states and having events year-round throughout the nation, he should be. His dedication to conservation and cleaning up public lands, while somewhat unorthodox, is not only entertaining but successful. “It's about taking the environment back out of partisan politics.  Vegan birdwatchers have more in common with sportsmen than the apathetic masses who don't care about the outdoors.  We may not always agree how to use it but we must support agencies that steward it, or it will be trashed then auctioned to the highest bidder.  The value of these great places is inherent in their existence not “What can I personally extract from them?” Conjecture and hyperbole get us nowhere, that's why we just decided to have fun, clean shit up and hopefully everybody else joins in.” explains Morgan.

As Harlan and Brodie pull into the waypoint at the border of national forest and the central Oregon high desert, we said our goodbyes and I paid them with a bottle of Azeo Vodka for the ride. Gamblers file in to the small spot, hang out for a few minutes, then make their way to the next waypoint further down the mountain. It was still early in the day, around 9:00 am, and the stories from this trip were quickly filling the pages of my note pad. After hanging out at the first waypoint for about an hour, I shift gears and begin searching for a ride that is the least likely to break down, has an empty seat, and probably won’t murder me and leave my body in the forest. Just then a crew of three people dressed in camo, sporting Rainer Beer shirts, and with one person riding on the roof of a Mitsubishi Montero that has been rattle-canned OD green pulled into the makeshift parking lot… surely these gentlemen would appreciate a bottle of vodka in exchange for a trip to the next stopping point.

Joel Green, another custom knife maker (  nstagram.com/gritcitycustomknives )  agrees to allow me to ride along with him, Brandon Lockwood, and Joe Brentin on another leg of the trip.

Joel Green, another custom knife maker (nstagram.com/gritcitycustomknives) agrees to allow me to ride along with him, Brandon Lockwood, and Joe Brentin on another leg of the trip.

The final destination for the day was Hoodoo Ski Resort, which lays right beside the PCT on top of the cascade mountain range, where everyone will camp for the night. Live music, good beer, even a recommissioned city transit bus being used as a tattoo parlor will be there, not to mention hundreds of pounds of trash that was once strewn about the public landscape, now gathered and ready to be appropriately disposed of by a bunch of rednecks, dirtbags, and gearheads who found a way to clean it up when nobody else would, and had fun doing it. 

Camp the following morning, before everyone recovered from the events of the previous 24 hours

Camp the following morning, before everyone recovered from the events of the previous 24 hours

The following morning came early. I made the decision to join Tate in his Toyota Tacoma and make a quick trip to Portland to prepare for the end of the event which was being held at Portland Meadows, a racehorse track that had enough parking and a field big enough to accommodate all the Gamblers. Garbage was weighed and counted. Cars were auctioned off for Children’s Cancer Research. Prizes were awarded. As with every step of the way, and throughout the history of the Gambler, it’s abundantly clear that Tate plans to grow his “overland adventure rally” in a way that doesn’t just live up to the original ideals of the Gambler, but also leaves every acre of public land that they touch better for it. Sponsors may come and go but the legacy of the Gambler will be long lasting. Beware all litterbugs, Woodsy the Owl has a new gang of misfits in his corner. 

Joel, Joe, and Brandon celebrate arriving at the finish line, even if it was on a tow truck. The “5 cylinder V6 Monster” as Brandon so affectionately called it didn’t quite make it all the way without assistance… but nobody cared. Not to mention they now had a designated driver.

Joel, Joe, and Brandon celebrate arriving at the finish line, even if it was on a tow truck. The “5 cylinder V6 Monster” as Brandon so affectionately called it didn’t quite make it all the way without assistance… but nobody cared. Not to mention they now had a designated driver.

This car had never seen this much fun in its former life.

This car had never seen this much fun in its former life.

Michael Young getting a tattoo on a former city bus that has been converted into a mobile tattoo parlor.

Michael Young getting a tattoo on a former city bus that has been converted into a mobile tattoo parlor.

Toolboxes are optional. Being a resourceful mechanic is a necessity.

Toolboxes are optional. Being a resourceful mechanic is a necessity.

One of the teams with their haul of garbage being counted and weighed at Portland Meadows.

One of the teams with their haul of garbage being counted and weighed at Portland Meadows.

The finished product. Michael Young, just before having to break the news to his wife that he now has a Gambler 500 tattoo. He’s currently still married and breathing… so she must be a really good sport.

The finished product. Michael Young, just before having to break the news to his wife that he now has a Gambler 500 tattoo. He’s currently still married and breathing… so she must be a really good sport.

For more information, and how to join in on one of your local events or the OG in Oregon, go to https://gambler500.com/.

Justin Moore2 Comments