Sitting in camp at the Millican Valley OHV outside Bend, Oregon, I watched a three-legged dog in a Day-Glo orange vest bark and snarl as he chased around a motorized three-wheeled grocery cart powered by a 212cc engine. The guys behind the contraption are my new neighbors, four youngsters from Hillsboro who dub themselves the “Delivery Boys,” and who also brought a minibike with a raked-out front end and Z bars to the big dance in the desert. The mini-chopper is the work of “Delivery Boy” Simon Pennington, affectionately called “mad scientist” by his buddies, and after seeing the crazy grocery cart, I can see why. It’s the night before the Oregon Gambler 100 Mini Bike Enduro, an off-road race on inappropriate machines whose overachieving engines and suspect suspension aren’t necessarily built to be flogged over rugged terrain for 100 miles. Such is the beauty of the Gambler racing series.

Oregon Gambler Mini Bike Enduro
The Gambler series of races always invites a diverse crowd. And that’s just the vehicles.Bryan Harley

As the sun made its way west over the Cascades, the OHV staging area bustled with energy, transforming into a dystopian community of campers, survivalists, and other living-on-the-fringe types on the outskirts of Oregon's high desert. A beater of a Lincoln limo rolled in and immediately drew a crowd, the old stretched-out Continental lifted and shod in all-terrain tires, a row of high intensity floodlights, a pop-up tent, and a minibike mounted on its roof rack. The “Sketch Limo,” a.k.a. #24feetoftheamericandream, is a veteran of the Gambler 500 Rally, the irreverent, mostly off-road rally-style adventure for cheap, impractical, fun vehicles (where participants spend no more than $500 on their rigs) from whence the minibike bash spawned. The “Punisher” parked nearby was also OG, the all-wheel drive AMC Eagle murdered-out in flat black, its front end fortified with an industrial-strength steel bumper and twin wenches.

murdered-out AMC Eagle
This murdered-out AMC Eagle is a veteran of the Oregon Gambler 500 car wars. Hot sauce optional.Bryan Harley

The ensemble of modified minis was just as eclectic as the other vehicles in the compound. A three-wheel-drive minibike, its in-line wheels connected by a series of chains and sprockets, earned a lion’s share of compliments for its engineering. A minibike with a single-sided fork on its right side and a single-sided swingarm on the left also garnered plenty of praise. Another competitor ponied up, adding a horse saddle, leather saddlebags, and a rifle holster to his trusty two-wheeled steed. Mixed into the menagerie of the peculiar were mini standards like Coleman’s CT200U-EX, Baja Doodle Bugs, and Honda trailbikes.

As the night settled, my neighbors began blaring Europe’s “The Final Countdown,” and the campy tune felt oddly appropriate on the eve of the big race. Flames of the bonfire danced ever higher in the background as minibikes buzzed around the campground like mosquitoes. Laughter became a constant, and even more so when a daring few hopped on their minibikes and tempted fate by launching off a ramp over the fire. Although “roasted rider” wasn’t on the night’s menu, one unlucky soul got a healthy taste of Oregon dust after landing on his face.

lineup included this custom fat-tired
The lineup included this custom fat-tired, single-fork number…Bryan Harley

The next morning I woke to Queen’s “Radio Ga Ga” and realized that somehow ’80s cheese rock had become chic. After morning coffee I caught up with Bryan Toller from Salem, Oregon, who, in underground fashion, has worked diligently to promote the event via social media. The day before the race Toller put together a posse who hauled trash from the three staging areas and 66 miles of trails at the park. While Gamblers are all about fun, having minimal impact and respecting the environment are also prioritized. And although Gambler 500s in four-wheeled vehicles have been going on for a few years now, Toller said this was the first competition featuring minibikes.

“This event triggers something from your childhood,” he said, and after looking around at the motley crew gathered for the Gambler 100, I realized that statement hit the nail on the head.

classic Honda Trail 70
…as well as this more sedate, mostly stock classic Honda Trail 70.Bryan Harley

As the clock ticked closer to the 10 a.m. starting time, the big board with sign-up sheets began to fill up. The cast of characters was colorful, wearing clown suits and rainbow wigs to a leopard-print catsuit to a full-on Evel Knievel costume complete with a cape. Team names were just as creative, with Mr. and Mrs. Miyagi set to battle the British Death Fleet, and Hang Belly Express ready to deal with Lowered Expectations. Eagerness became palpable as Gamblers made last-second inspections of fuel levels and tire pressures. Race organizers added to the drama by announcing it would be a running start, so 102 riders lined up side by side would sprint to their minibikes from across the road, yank their pull starters, then jockey for position down the straightaway. Pandemonium ensued as riders parked in the middle of the pack heard the signal to start long before people on the periphery. A huge dust cloud arose as the first racers rocketed by, minibikes jousting five wide as others disappeared in the storm. Some riders, realizing that just finishing the 100-mile race would be a battle of attrition, waited until the dust settled before taking off, this second wave including the “Godfather of the Gambler 500,” Tate Morgan, on his Coleman CT200U-EX.

sign-up board
When we got to the sign-up board we got a taste of the madness to come.Bryan Harley

It didn’t take long for pecking orders to be established over the 5.6-mile-long course. Those with more experience and horsepower pushed to the front while others set a more leisurely pace. Organizers were wise to start the course with a long opening straight, as riders could run this pretty much wide-open, helping to spread out the herd. There were primarily two lines along this stretch; the preferred sandy, smoother inside line and the rockier, rougher outside one. A serious switchback awaited at the halfway point, the turnaround followed by a path of fine powder. About the time riders got a groove going the trail would get more technical, and the rocky staircase known as Devil’s Butthole would sneak up.

This part of the trail lived up to its name, creating pucker moments for a few riders who were tossed over the handlebars on the challenging decline. Soon after came the rhythmic roll of the whoops as the course wound back to the staging area and the starting line. It didn’t take long for the Gambler 100 to start claiming victims, as mechanical gremlins and gas miscalculations began to take their toll. In true Gambler spirit, riders rallied to help the stranded get back on the road. Support ATVs were busy towing the broken-down bikes back to camp while a handful of riders made the walk of shame back to their minibikes with gas cans in hand.

minibike race around 5.6 miles
Team names like this set the tone for a minibike race around 5.6 miles of occasionally treacherous terrain. No, we didn’t see any Norton Commandos in the race.Bryan Harley

After spending most of the morning photographing face-plants at Devil’s Butthole, then watching the ambulance cart off an unlucky rider, a stroke of good fortune came my way in the afternoon. My newfound friend Jason Lightner of Team Goldicocks asked if I’d like to spin a lap on his camouflaged Coleman minibike. Lightner’s partner Andie Rotner was one of the few girls competing in the event, and the two-person team had already logged a dozen dirty laps. Filled with the spirit of the Gambler, I couldn’t wait to take a turn.

Hopping on the Coleman came with a warning. The brake cable had lost most of its tension from the abuse it had already been taking, so there were virtually no brakes.

“Feet work,” Lightner said with a smile.

“It’s yabba-dabba-doo time!” I replied.

Oregon Gambler 100
The start of the Oregon Gambler 100: a buzzing dust cloud of spinning wheels and wild costumes.Bryan Harley

One advantage I held was the fact that I’d already run the course on my mountain bike to shoot photos so I knew the layout. I’d never ridden a Coleman minibike before so there was a bit of a learning curve, though it didn’t take me long to realize the mini’s meaty tires provided much better traction than the skinny ones on my mountain bike. I figured the 6.5-hp engine would struggle with my big body but was delighted to learn the torquey little number ran best on the throttle. Even though the first stretch was straight I still erred on the side of caution as I figured out traction and balance. Then I got passed by a clown. A red, yellow, green, blue-haired clown. I picked up the pace.

Devil’s Butthole section
The Devil’s Butthole section of the course served up a scary slide down a dusty slope, creating plenty of pucker moments for the racers.Bryan Harley

That Coleman minibike handled the course like a champ, from smashing rocks to flowing over whoops. It didn’t skip a beat, even when I crossed up the front after catching air over a berm. The more I rode, the more fun it got. I even tracked down the clown near the finish line, but he still beat me. The experience left me with a burning desire to buy my own Coleman minibike.

Clearly this guy isn’t wearing appropriate riding gear. Unless the sweater vest is made out of Kevlar.Bryan Harley

Team TJR was the first team to complete all 18 laps, albeit with their rider fittingly crossing the finish line with the bike’s seat in his hand. Each rider on the eight-person team got two laps aboard a Monster Moto 212cc minibike, and while most teams lapped in the 16- to 20-minute range, Team TJR’s sixth rider ripped off a 13-minute hot lap and followed it up with a 14-minute trip around the track. You could hear their Monster Moto approaching long before you saw it, thanks to an exhaust that sounded pissed off.

Winner of Oregon Gambler 100
And the winner of the Oregon Gambler 100, by a government-owned bumper, is Team TJR.Bryan Harley

Long after Team TJR had checked out, teams continued to pound out laps, determined to finish the race. Completing the race comes with bragging rights and a sense of accomplishment, but at the Gambler the emphasis is on fun, above all.

“First off, thank you to all that volunteered and helped out. The weekend was amazing because of you. Big thanks to the 24 people that participated in the trail clean-up,” Toller wrote on the event’s Facebook page. “Without a doubt the ride was an endurance challenge. 102 bikes started the ride and only 46 finished the 100 miles. Everything but my tailbone is looking forward to doing it again next year!”

three-wheeled grocery cart
We were hoping to see this three-wheeled grocery cart contraption in the hunt, but it seems it was only used as a pitbike. Or something.Bryan Harley

Two days later I’m still picking dusty crusties out of my nose. The grin I wore when I jumped off Lightner’s mini is still there too. I’ve been bitten by the Gambler bug and there’s only one known cure: See you next year at the Oregon Gambler 100 Mini Bike Enduro II.

chopped-out mini
Then there was this really cool chopped-out mini, appropriately dubbed Misery.Bryan Harley
105th-Anniversary-Harley-Davidson-fuel-tank-wearing machine
And this awesome, 105th-Anniversary-Harley-Davidson-fuel-tank-wearing machine. Check out those bars.Bryan Harley
bonfire jumping
The party continued before and after the races, with slightly insane events like bonfire jumping lasting into the night. Evel would be proud.Bryan Harley