Always Be Gambling: 2019 OG Gambler 500 Recap

Day 1

The day is June 28, 2019; it is a calm summer morning in Portland, Oregon. I wake up to find three missed calls from Aaron Stewart, my guide and mentor for my first-ever Gambler 500. He’s waiting outside in his 1985 Pontiac Fiero, cut-up and welded together to transform into the “Rallyero,” as he calls it. It’s missing interior panels, windows, and it’s spray-painted black all over.

We set out on the open road. His Fiero catches a draft when pulling behind semi trucks. 40 feet back is the “sweet spot”; outside of it, he can “feel” the car slowing down. He gets his speed readout from a smartphone app, since the speedometer hasn’t worked in forever. The open-air cabin and blasting dashboard-mounted speakers do a number on my eardrums, so I throw in my ear plugs and take in the scenery as we drive on.

Clockwise from top left: The Team Full Send roster – Aaron's Pontiac Fiero (aka Rallyero), Dillon's Toyota Celica, Jorge's Hyundai Accent, and the short bus.

We met the rest of the group in the morning. Specifically, we have a 1986 school bus, a ’90s Hyundai Accent, an ’80s Toyota Celica, and the Rallyero. After a session of final checks – drilling in a 90-degree piece of PVC pipe for a cup holder, writing slogans in chalk on the bus – we head south on the I-205 toward World of Speed. Aaron’s speakers blast everything from ’80s hits to bluegrass country. He mentions picking up a new fuel pump and an air filter, the latter of which he completely forgot to install before our journey. Nothing gets in the way of forward progress on these rigs.

The World of Speed in Wilsonville, Oregon is one of our first stops.

At World of Speed, a car museum in Wilsonville, Oregon, a few dozen Gamblers arrive to admire each others’ work. They include:

  • A ’91 Corolla with its roof hacked off and given a bed, in the sense that a Sawzall, expanding foam and Bondo can provide a bed.
  • A ’90s Grand Cherokee with a hood scoop on the roof and graffiti’d exterior.
  • A purple Pinto that raced on drag strips now has used up all-terrains and a wooden rear bumper.

An assortment of the Gamblers at World of Speed.

All of these rides (and more) are what I’d call “ugly-beautiful.” They trigger a distaste initially, but that gets bowled over by the admiration of ingenuity, as well as the hilarity of some of these mods.

After a little stop to get some gas and food, we’re back on the road again. Now we’re heading to Conversion Brewing in Lebanon, Oregon. We went past the state capital, Salem, a few miles back.

After World of Speed, we cruise through Lebanon to find Conversion Brewing, where official Gambler waypoints are listed for those interested. We also see some more hilarious builds; and yes, that is expanding foam holding in the Grand Cherokee's auxiliary lights.

The first waypoint is “Damn Near” and it’s damn near a dam. Green Peter Dam, to be exact; a 50+ year old construction holding up a 10-mile long reservoir and generating 80 megawatts of electricity. The greenery of pine trees on either side make it a breathtaking sight to see.

Team Full Send’s group photo at “Damn Near” the Green Peter Dam.

Waypoint 2 is Dogwood Tree Picnic Park, aka “Dogwood.” It’s another beautiful area, lush with green and a running creek. Moss grows on the trees and adds to the beauty, but this isn’t a sightseeing journey; it’s a Gambler, and we’re going all-in.

Some 30-40 miles from Dogwood, the gambling hits a snag. The Hyundai Accent conks out on an uphill mountain road. The throttle was having problems but it got back up again, only to fail again soon after. Was it the fuel pump? The fuel filter? A clogged cat? Whatever it was, Dillon, the Celica driver, says it best: “This is gambling! You go ’til something breaks!”

The Accent is the first car in our group to suffer a breakdown. After some tinkering, it's back on the road, sans emissions equipment.

Back on level ground, the Accent is running again. Starting the simplest solution – the air filter – the group begins examining the car. The filter looks clean, so that can’t be it. Dylan busts out his minibike and starts riding around.

The coolant looks clean, the oil level is fine. It cant be the head gasket, there’s no leak visible. Everyone is scratching their heads about what’s plaguing the car. Maybe it’s emissions equipment? Someone undoes the throttle position sensor and asks Jorge to test it. He does and makes it around the bend. Glory glory hallelujah. We’re back on the road.

This is gambling! You go ’til something breaks!

A mudhole trail entrance off of the beaten path. Of course we check it out!

We drive a few more miles and spy an entrance with mud. Cue the group pulling 10-point turns to get on the trail. Aaron and I go through first. The group follows and a driver in a ’90s Mercedes sedan comes through. He and Dylan get to talking and it turns out the Merc’s radiator is leaking. Dylan does the neighborly thing and offers stop-leak putty. The Merc driver offers a shot of something in return. “Sounds good, but it better not be Malort!” jokes Dillon.

The process turns into shots and fender clearancing with pieces of rotted wood. The wood wedges between the tire and rolls the fender out as the wheels move. Talk of pry bars and sledgehammers abounds.

How to fix a leaking radiator and rubbing tires? Easy. Just use putty and an axe!

A few minutes later, we’re back at it. We keep driving until we see a turnout and take it. Driving down the gravel path shows us trees and fallen logs, weeds, and dirt cliffs. We finally reach a vista and it’s a remarkable one. To the east is Mount Jefferson, blanketed in cloud cover as the 5pm sun lights it up perfectly. Snow runs up and down its slopes and while there are no amber waves of grain, the majesty of this purple mountain is no less diminished.

But this sideshow came at a cost. We still have 3 hours until we make camp in Chemult. We’ll have barely any time to get the tents assembled. So now we have to commit to the trail and get back on the main road ASAP.

We’re here!

Within 45 minutes, we’re in Sisters, Oregon. It’s a quaint little town with an assortment of restaurants and boutique shops. There’s even a laser tag and movie theater. Refueled and fed, we continue on as we head to Chemult. We’re going to arrive very late in the day, with just a few minutes of daylight.

We set up camp and listen as a death metal band called “Trojan Swamp Monster” lays down some bars. I get my tent sorted and take off my working-man hat, and proceed to relax with the fellas. I even take my first ride on a mini-bike, and wipe out after trying to do something cool.

Day 2

The next morning I’m up as the sun is past dawn. I start walking around the grounds in search of a high-rolling Gambler.

In the cold light of day, Gamblertown is like a decentralized Hammertown from King of the Hammers. There’s no main area; everyone is spread out and sprawling amidst machinery, pumice dust, and the odd clump of pine trees. You hear the putt-putting of mini-bikes and roaring V8s roving around. I make my way to the outer reaches and come across Matt and his beat-up Ranger.

Matt and his crumpled (but "running") Ford Ranger give off peak Gambler vibes.

Matt is tearing into the engine bay to take care of a bad head gasket. The truck barely made it from Bend all the way down here to Gamblertown. Everything in the bay is pushed in on either side from a “rallying” accident Matt had. He’s making progress and the truck is making me laugh with its various inscriptions like “I ❤ MILFS” and “This is a professional race vehicle, please do NOT touch!”

As I return to camp, Aaron says to follow him; “You ever ridden in a Robin?” he asks. I think maybe I’d misheard him; surely he doesn’t mean an actual Reliant Robin.

The Reliant Robin, in all of its jury-rigged, duct-taped, and pop-riveted glory. The fiberglass body is barely hanging on for dear life, but that's what makes the Robin one of the most awesome Gambler builds!

We journey to another camp to find a Reliant Robin. You may recall these from Top Gear, when Jeremy Clarkson took one bounding about England and got it to roll over quite easily. I had qualms, but the feeling of riding in one of these things was too good to pass up.

No hi-lift jack or wheel ramps? No problem, just use a little plastic cooler.

One thing I learn about the Robin is its fiberglass body. Chad and Kevin, the builders, are busy keeping it in one piece, using aluminum, zip ties, duct tape, and rivets upon rivets. “I think I have about 166 pop rivets in this thing,” Chad says. “It’s a veteran of being rolled, but from previous owners. I’ve never rolled it myself.”

Taking his word for it, we leave camp. I’m the very nervous passenger of the Robin. To my surprise, we never get near the point of tipping, although passing a convoy of people on a two-lane road still haunts me.

We are going to pass the guy in front of us, and did so, only to find an oncoming Ram 3500 boat-tower coming directly at us over a crest. Chad goes screeching to a terrifying halt, cutting in the nick of time back into the appropriate lane. I stomach the experience and let Chad keep going.

Gamblers from all over wait to test their mettle on the HooptieX course.

We find the road that leads through a forest, unveiling a lumber complex. This is the site of HooptieX, a.k.a. HooptieCross. It’s here where gamblers drive their rides around a medium-sized course. It was built into the land of a defunct lumber operation, but its layout and spectators are lively.

I watch one after another make their way through the course. Even Chad and his Reliant Robin make the grade. Not once does he get the thing to roll; truly, he has the skill to keep his “three-legged dog” upright.

The Robin takes a parade lap around the HooptieX course, and does it all without rolling once!

We journey back to camp and I decompress for a bit. It’s not everyday that I almost meet Jesus in a fiberglass, gas-powered tricycle.

Afterwards, I walk around camp and meet up with A.J. Butler and his gleaming red Dodge Ram. His truck build is an incredible cross of Angry Birds and craftsmanship. You’ll get to read the article on it very soon.

Some more sights from HooptieX.

The rest of the night is easygoing. I watch a movie with the fellas and hit the hay soon after.

Day 3

The second day in Gamblertown sees the decomposition. Everyone is packing up and rolling out, myself and Team Full Send included. Tents are disassembled, gear is loaded up; the whole nine yards.

Not many people are sticking around, and several members of Team Full Send are going their own ways. Aaron sees the situation and decides to head out early as well. We link up with a couple of friends of Team Full Send. They’re driving in a Chevy van. Our Fiero and their van make a mini-convoy and heads out of camp, taking the scenic route home by way of Bend, Oregon.

After leaving Gamblertown, we take the scenic route home, stopping by Clear Lake to soak in the natural beauty.

After stopping for a nutritious and well-balanced Taco Bell breakfast, we continue on. We make it to Clear Lake, a beautiful body of water nestled near Mount Washington. Geese and butterflies flit around as we take in the scene and relax.

We hop back on the road, the friends peeling off after some time to go their own way. It’s late afternoon when we finally get to the outskirts of Portland, and make it back to Aaron’s house in Troutdale. At long last, the Fiero and its squealing fuel pump earn some much-deserved rest.

Mount Hood looks exquisite as we drive by.


The Gambler 500 was an incredible experience. Looking back, I think embedding with a team was the wiser choice when compared with building my own Gambler and driving all the way up. I broke bread with some of the coolest and funniest people I’ve ever met, and got down and dirty in rigs that would make overlanders blush.

“When I get up in the morning and I take that first sip of water, I look up at the sun and I’m grateful for every adventure that we have,” said Tate Morgan during Saturday’s awards ceremony. His words resonate with me now, as I think about how many personalities I met during the weekend, from the carefree Chad and his rattling Robin to Matt and his busted-up Ranger, along with all the incredible guys and gals of Team Full Send. Every Gambler and his build had a story to tell.

Everyone should do the Gambler 500, even if it's just to see the jaw-dropping weirdness that rolls through!

I look forward to checking out another Gambler 500 in 2020 – or even sooner! The nice thing about the Gamblers is that there seems to be one every month to two months, and they’re all over the country. I encourage you to check out Facebook to find local Gamblers near you, and remember – Always Be Gambling!

Always Be Gambling!

About the author

David Chick

David Chick comes to us ready for adventure. With passions that span clean and fast Corvettes all the way to down and dirty off-road vehicles (just ask him about his dream Jurassic Park Explorer), David's eclectic tastes lend well to his multiple automotive writing passions.
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