Off-Roading in Iceland with $500 Cars: The Best Kind of Gamble

The Gambler 500 ethos of no expectations still reigns supreme even in the Icelandic Highlands.

Chris NelsonWriterJade NelsonPhotographer

I felt bad for our photographer because I couldn't answer any of the numerous questions he had ahead of the trip. He knew everything I did: We would travel to Iceland, and beneath a midnight sun, we would ride pull-start minibikes and drive $500 cars through the desolate Highlands. I told him as much, but he wasn't convinced. All I could say was, "Don't worry. This is how the Gambler 500 works."

The Gambler 500 started as an email chain between friends who decided to go off-road in $500 cars never intended to be driven off-road. There would be no winners or losers, and there were only two rules, which remain the event's only rules: clean up the trail as you go, and don't be a jerk. On weekends they met at Wanker's Corner Saloon outside of Portland, Oregon; someone handed out sheets with waypoints, and off they went down trails in anything from a Toyota MR2 to a Cadillac Fleetwood. "People try to buy respect or admiration, but they earn it by driving a Corolla," Tate Morgan says.

Morgan is the Gambler 500's face. Most of the time, that visage is covered by rainbow-colored Lazer Face sunglasses, which looked idiotically fashionable paired with the bushy, full-length fur coat he wore in Iceland. He is congenial and considerate to everyone, but not everyone loves him. The people at Pop-Tarts and Meow Mix most certainly hate him because he made them fake sponsors of the Gambler 500, and when the companies reacted horribly on social media, Morgan called them out in hilarious ways. He didn't create the Gambler 500—it just sort of happened—but he did mold it into what it is today. Four years ago, he contracted testicular cancer and lost a cojón, so he quit his corporate career and dedicated himself to spreading the Gambler's good word. "There is no goal in the Gambler," he says. "If you set expectations or a goal, then you have steps to get to that goal. If you have no expectation or goal, then you get to free-form it and let it be what it is."

A week before we visited Iceland, the Gambler 500 hosted its biggest event of the year, the fourth annual "OG" festival in Oregon, where more than 4,500 people showed up in more than 2,800 vehicles, including a boat mounted on a truck frame. I first experienced the Gambler last year at its inaugural 100-mile Mini Moto Enduro. Although I anticipated leaving with a bruised behind, I never would've guessed how amusing a 6.5-horsepower minibike could be or how well it handled serious trail riding. I also really enjoyed the Gambler 500 community.

The tagline of this rally for automotive freaks and oddities is "Always Be Gambling." When stuff inevitably happens, tell yourself "ABG" so you don't lose your head.

"No one is making fun of your car or making fun of you, and you're immediately accepted because we're all in the same place, doing this dumb thing, and we depend on each other," Morgan says. So when these strange and magnanimous people invited me to be part of Sjit Run—the Gambler 500's first overseas event—I knew what I was getting myself into.

Staff photographer Jade Nelson did not, however. He had not met the Gamblers, so he couldn't understand when I told him I had no idea where we were going or where we'd sleep or any other information he might want to share with a loved one before disappearing into a volcanic desert for three days. His stress melted away after we landed in Reykjavík and met "Chicago" Tom Chemler, who is selfless with his carton of Lucky Strikes and is sponsored by Jeppson's Malört, a cult liquor from Chicago that tastes how dandelions must taste. Chemler has attended 30-plus Gambler events, and in Iceland he drove an '01 Volkswagen Polo with heat stuck on blast, windows that wouldn't roll down, and windshield wipers operated by a handheld string. "Other than that, it's got nothing else going for it," he jokes before explaining why none of it matters. "The Gambler 500 is a completely different horse. It allows you to be self-reliant, sort of 'you as an island,' and there's not a lot in a lot of places that can help you."

"If you set expectations or a goal, then you have steps to get to that goal. If you have no expectation or goal, then you get to free-form it and let it be what it is. "

I wouldn't be able to help Nelson because I was riding flat-out in a group with seven other men on de-governed minibikes, with Viking horns duct-taped to our helmets—and he couldn't help me because he was seeing firsthand how absurd the Gambler 500 gets. When he arrived last to camp at the end of the first day and stepped out of the Toyota Previa he hitched a ride in, he told me how his Gambler experience started with Chicago Tom hitting a volleyball-size boulder and ended with the Previa high-centered on a pile of rocks, which punctured the gas tank. A few Gamblers patched the tank with a ratchet strap, which required the Previa's sliding door to remain open, while the rest of us stood around a fire, passed around communal lamb legs, and watched the Americans jump minibikes over the flames before event organizer Xárene Eskandar put a stop to it.

Andy Munson on a minibike in between stints driving his '78 Cadillac Fleetwood.

Eskandar drives a '79 Cadillac de Ville on a six-inch lift, splits her time between Los Angeles and Iceland, and is a radical environmental activist. She told me that of everyone attending the rally, only one Icelander had ever visited the Highlands. She hoped the event would raise awareness about the Highlands because it is being targeted by the European energy industry to build dams and produce hydroelectricity.

"Who is the authority to decide on what is beautiful and what is ugly, and to destroy unique ecosystems and landscapes for short-term gain?" she asks. Everyone who traveled to Iceland immediately understood it as something unique, intimidating, and vulnerable: the lava fields, the soft black sands so porous that precipitation supports only the most robust types of vegetation, and the massive glacier Hofsjökull in the distance. Off-trail driving is illegal because 4x4 tires create deep ruts that cause unnatural erosion. If you decide to drive off the trails, you'll pay fines exceeding $1,000.

The next morning we come to a river crossing, the minibikes running wide along a rocky shelf but the cars driving headlong through the deep glacial water. Amanda and Bobby McAuslen of Boise, Idaho, fish out the exhaust off their 1991 Lada Niva and reattach it with a length of speedometer cable. They bought the Niva from a local owner knowing it didn't run and that its clutch slave cylinder had failed, and they "restored" it with a pocket knife. Why did they fly 3,700 miles to attend Sjit Run? Bobby calls it a once-in-a-lifetime opportunity and adds, "There are people from different schoolings, trades, backgrounds, races, everything, and we all have one thing in common, and that is this obstacle of this trail and how we're going to get all of our carnage through it and not leave anything behind."

I don't make it far beyond the river before my minibike's chain breaks, twice, and I end up in the passenger seat of the Sprinter 4x4 support van, where I spend the rest of the day talking to Morgan's dad about his 32 years as a hydrogeologist for the United States Geological Survey. We camp that night along the coal shoreline of Iceland's largest lake, Thorisvatn, and on the descent into camp the Sprinter gets stuck behind a stuck Toyota FJ80, blocked by a stuck Subaru wagon, both slowly spinning themselves deeper into the black drift. Nelson arrives at camp after most of us have gone to bed, driven into our tents by a steady rain. His day went as follows:

You'd be screwed if the gas tank fell out of your Toyota Previa, right? Not as long as you had a ratchet strap.

The Previa shed its exhaust from the manifold back; both passenger-side wheels were righteously dented, and Chicago Tom bent them back into shape with a rock; and the gas tank fell from the van's belly about a half-dozen times. At the river crossing, the accessory belt snapped, but Gamblers managed to remove the tensioner and replace the belt with three daisy chains of multicolored zip ties. The zip ties spin the water pump but not the alternator, so every 30 minutes they swap batteries between the Previa and the Polo. It works, but by the end of the day, the Previa vomits fuel and is marooned at a gas station outside of the Highlands. At 2 a.m. Nelson jumps into a Jeep driven by native Eggi, who has an assortment of jetsam piled in his rooftop basket.

In the morning I drink instant coffee with Kjartan Gudmundsson, who built his Jurassic Park-themed Toyota RAV4 in 25 hours, including the one-off PVC snorkel. Kjartan discovered the Gambler 500 event on Facebook and tells me that two years ago, he and his brother were in this area in a Land Cruiser on 38-inch tires and thought "it would be cool to drive across the Highlands in a piece-of-shit car." We speak to another Icelander, Erla Gunnarsdóttir, who had previously accompanied Eskandar to Gambler events in Arizona, California, and Utah. In Iceland she rides as passenger to a burly, red-bearded American who drives a '91 Toyota Corolla wagon with a welded rear differential. She loves seeing her country through someone else's eyes and says the Sjit Run feels like any other Gambler event: "The same good crowd, same good vibes, and same good feelings."

The river was unkind; the Lada Niva's exhaust fell off, and the Previa's accessory belt snapped. The exhaust was reattached with a speedometer cable and a replacement belt made from zip ties.

When Nelson finally emerges from his tent with half-open eyes, he is smiling. He looks different after all of his hilarious suffering, and he now understands why you should go into a Gambler 500 not knowing what to expect.

"It seems the whole idea of Gambler is to have as few expectations as possible and just go with the flow," he says. "Coming into it I struggled with the lack of structure, but once it started, I realized the lack of structure was inevitable, and I was able to enjoy the event as it is meant to happen. Everyone involved feels this sense of freedom, and because of that, everyone is always in a good mood."

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