The gambler 500 is not only the coolest race/not race on the planet, it is also the largest trail cleanup in Oregon. it started in 2014 when Tate Morgan (the founder and) and 14 other cars decided to get the least practical, most ridiculous cars they could find and use as few roads as possible to reach a destination. as the saying goes “The pavement is lava.” Check out the backstory here.
My best friend and I decided to join in 2019 when we heard that they had a route starting in Lebanon Oregon and ending in Chemult, OR. I am not only familiar with these back roads but the idea of driving the most ridiculous vehicle we could find gave us both a hearty chuckle.
The race was on before the race began as it relates to my friend Eddie and my plan to see who could find the most ridiculous vehicle.
I won when I sent him a receipt for a Chinese moped being shipped to me that came in right under $500 (before shipping, but don’t be a dick about it) that TaoTao 149 was a real beaut.
*Disclosure: I get commission if you buy through these amazon links*
I received it 4 weeks later and only then found the capacity was 300 lbs. I asked Eddie how much he weighed, hoping he would say 60 lbs, as I was 240 at the time. It turns out being a big hairy 6’2″ Russian, that would be tough. We ended up right around 460 lbs. before our gear.
I knew we were going to need a little extra juice so we made some performance upgrades by spray painting the moped and adding an American flag air freshener. Getting it to what i would guess was close to 10 hp.
We planned on riding it beforehand, but never quite had time and the June 28th deadline was approaching fast.
We ended up never trying it out before hand and decided we would just wing it, as is tradition.
The day before we went to value village our favorite thrift store and picked up the ugliest suits and ties we could find in the spirit of the gambler and loaded that bad boy into eddies truck in order to get it to Lebanon.
We arrived at the start point at Conversion brewing and unloaded the moped and geared up. only then realizing that going over 200 miles through the woods on no pavement may be more of an undertaking then we originally thought.
But we had a few beers and decided that two guys on a moped is better than no guys on no moped and we were off.
Our first way point was a dam, on the way another gambler car handed us a beer (of course only Eddie drank it being the passenger)
We were passed by hundreds of cars, some gambler some not, topping out our little moped around 48 in a 55 where we met up with two of our friends finally at the dam.
I would like to take a moment to talk about moped safety and included a video of a friend who decided to drink too much and moped.
After the dam we began following a road that got more and more bumpy, and less and less paved and finally we went fully off-road, bouncing and sliding and punishing our lower backs in a way few people will ever experience. It was about the time we went off road that we realized we were nearly out of gas and had to steal some from a friend of ours, and really hoped there was a another gas station as we had a two gallon tank and were getting probably 30 mpg the way we were driving.
The gambler is based on way points here is the app they use so you just try to find the most creative way to get there.
We spent the next four hours off roading and stopping every once in a while with our buddies who were following us because their car kept getting vapor locked and refused to restart if we would turn it off for a break or refuel.
After we got higher and higher in altitude we began crossing the Santiam pass to bend because it began pouring rain and got extremely cold. One thing we didn’t consider is that the speed limit is 55 while climbing the steepest part of the pass and our moped would do barely 35 so before we knew it we were holding up cars as far as the eye could see, but we had to get to the next way point in bend so it was what it was.
we finally reached the brewery in bend, completely bedraggled and knew we still had quite a ways to go to get to chemult. So we had a beer and knew there was only one thing to do and that was to continue onward as fast as was possible on that tiny chiny moped of ours.
At this point time absolutely drug on, but we soon entered the town of Chemult and began to see it completely full of the most outrageous cars ever to grace the roads of Oregon all in one place.
My excitement grew as we saw our turn in and we made the corner and went back into the woods.
About a mile later we turned another corner and before us was a white wasteland straight out of mad max ful to the absolute brim with noise and cars and absolute insanity and we knew we had arrived at what was later dubbed “redneck burning man”
That night consisted of seeing how many people would fit on the moped at once (5) and who could make it the furthest up the pumice piles (this is a pumice pit after all). Then when the sun went down, a party like I’ve never seen began, their were cars on fire, people offering to show their lady bits for $1 or a beer and more people drunk and drinking in one place then I believe I will ever see again. And it was good.
Most of the night is a blur but I remember being a sour guy after a long day and giving up. Waking up with everything I owned and every orifice full of that tiny white aggregate known as pumice.
As I woke the realization that I would have to ride that moped over 100 miles on roads where it could barely half the speed limit sometimes really hurt me deep inside and I talked to my friend and decided there was only one solution. The moped must be strapped to the roof of their car.
Four strong guys and all the rope we could find later and we were off 4 deep in a ford explorer and I couldn’t have been more happy. The ford made it back to Lebanon and we made it back home in eddies truck. But my lower back will never forget the gambler 500.
