Home » Doing A Gambler 500 In Missouri Is Some Of The Most Fun You’ll Have On Wheels, And You’ll Do Some Good, Too

Doing A Gambler 500 In Missouri Is Some Of The Most Fun You’ll Have On Wheels, And You’ll Do Some Good, Too

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A few weekends ago, I took my broken Volkswagen Touareg down to southern Missouri for the state’s flavor of the Gambler 500 endurance rally. I expected drunken debauchery, car fires, and maybe even a hospital visit. But Missouri’s version of the Gambler 500 reminded me of why I beat up my cars off-road in these events in the first place. It was pure, unconcentrated fun, and we all left the state having left its trails and roads cleaner than when we came. This is why you do a Gambler 500.

If you haven’t heard of the Gambler 500 before, I’ll give you a rundown. The best way that I could describe the Gambler 500 is that it’s like that Wacky Races show, but in real life. It’s a 500-mile endurance rally meant to be done in cars as close to $500 as possible. This isn’t really a race, and you won’t get a trophy for finishing first. Instead, you’re encouraged to buy the worst possible car that you can find, send it through the woods with your friends, and remove all of the junk that other people leave behind.

I’ve been “Gambling” since late 2018, and I’ve seen some incredible trash pulled out of America’s wilderness. You’d be amazed at what people will dump into a forest or protected area. My teammates and I have yanked entire abandoned living room furniture sets out of forests, broken and abandoned boats, car batteries, countless tires, seemingly endless beer cans, and all kinds of other pollutants. Other teams have yanked out burned down RVs, abandoned cars, engines, appliances, you name it. And there’s often a charity aspect, too, as many of these events send giant donations to local area charities and food banks. At its core, a Gambler is about giving a helping hand to communities and having a blast while you do it.

Missouri describes its event like this:

The Gambler 500 enjoys a long history of land stewardship. This event is not a race, but rather a competition against your vehicle, and to see how much trash it can hold. In 3 events, we’ve taken and properly processed over 100 cubic yards of trash from the Mark Twain National Forest and surrounding areas. As a whole, the Gambler 500 events nationwide comprise the largest organized trail cleanup on the planet, and The Missourah Endurah champions that title in the Midwest region.

And like all Gamblers, it’s an event where everyone is welcome and the number one rule is don’t be a dick.

Unfortunately, in recent years some of these events have attracted people who have been unable to follow that rule. Some of those folks have brought along hate, some of them brought crime, and sometimes, the party got so out of control that emergency services got called. I’ve seen people steal cars and gear, and once, someone even set fire to a new-ish car that they were still making payments on. That’s just some of the unfortunate things that I’ve personally witnessed.

And I have to give a ton of love to event organizers, as they act quickly to get things back on track when this stuff happens. Still, some people have decided to distance themselves from these events because of those sorts of people. That’s why I adored Missouri’s run so much. It was a return to the event that helped make me the person that I am today.

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Between wedding planning, work trips, and unexpected neighbor trouble, I’ve only been on two Gambler runs this year. And the first technically wasn’t a real run. Normally, I’d do about four of these events a year, so my longing to go on another was strong. There are few things that I love more than taking some beater off-road with my friends and making new ones along the way. I’m also known for my unique way of trash cleanup and helping people out of sticky situations. One of my life goals is to swim in every body of water that I can find. So I’m the one to call when there’s trash at the bottom of a river or creek. I’m also there when you’re stuck in disgusting, head-deep mud. And I’ll happily do it in a dress. Doing Missouri? Oh, it was a grand return to form.

On September 9, I published my steaming hot take about Chris Bangle’s love for automotive booty. Then, I threw some tools and gear into my 2005 Volkswagen Touareg VR6 then took off for southern Missouri. I felt that the Touareg was a perfect Gambler rig. The worn out transmission valve body, its body damage, wonky electronics and other quirks make it the most beat up vehicle in my fleet. But at the same time, it’s also served me incredibly well. So to me, that makes it great at the job of a beater that needs to endure hundreds of miles of hard driving.

The Touareg and I arrived at the start point of the Missourah Endurah 2022 at 12:40 in the evening. Somehow, I beat Google’s original time to the camp by an hour. When I got there, most people were asleep, but there was a small drunken party happening in front of a cargo van. A full luminescent moon and clear skies made for a campground that was dimly illuminated, and quite peaceful. I enjoyed a couple of cold snacks with a friend that I hadn’t seen in over a year. For the both of us, 2022 has been such an odd year that neither of us had gone on a Gambler. This felt like old times.

I worked the whole day, just to drive another eight hours. So I was ready to tap out before I even got there. I’m not sure if the backseat of a Touareg is a good place to sleep, but I passed out for just three hours before the event’s organizers blew the wake up horn at 6 in the morning.

The Missourah Endurah 2022 Start

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On Saturday morning, a parade of epic cars began piling at the start line at Hooter Holler Off-Road Park in Mountain Grove, Missouri. I’ve written about the creative genius that were Missouri’s Gambler cars in the last entry, but my favorite still remains the Team Anchorman van. It’s that perfect mix of silly Gambler theming, but just obscure enough that the general public could be fooled by it, too.

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The cars here were a scrappy mesh of Gambler event veterans and first-timers. This Buick LeSabre, driven by a tow truck-driving friend, has been just about all over the country.

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The driver’s had to replace so many parts over that time from water pumps to wheel bearings, but the car itself just won’t quit. Oh, and that black paint? It’s house paint that has somehow stuck to the car through two, maybe three years of these events.

And of course, then there are some fresh faces like this Mercury Grand Marquis driven by Dalton of Pole Barn Garage. So Dalton told me, he bought the car for $400 after its previous owner slammed it into a deer. Instead of just sending the car to the scrapper, he decided to have it go out with a bang. It didn’t lose its roof until just four days before the event. It was hilarious how much the body on this thing jiggled without a roof.


The organizers called this run the Missürburgring, a reference to the famous Nürburgring toll road and track. I wondered why such a reference was made, and it all made sense when you plugged in the run’s coordinates into a GPS. View all of the stops from a satellite view and it looks like a rough outline of the Nürburgring, just scaled up to well over 300 miles.

The Drive

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One of the magical things that makes Missouri different from other Gamblers is that you can hit most of the checkpoints driving off-pavement about 95 percent of the time. Missouri has a vast network of dirt roads, and they range from easy gravel to washboards, water crossings and rocky climbs. Locals tell me that when it rains, these dirt roads can get so muddy that you aren’t getting through without a four-wheel-drive vehicle. There was no rain to be found this weekend, so it was oh so incredibly dusty.

But even as the dust filled my contacts, I couldn’t stop smiling. My team of misfit beaters hit the route, choosing to avoid highways and as many paved roads as possible. I tracked miles driven off-pavement and on the first day, we managed to trek some 200 miles on dirt roads and trails. 

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We stopped frequently to clean up trash from the side of the road and trails. Along the way, teammates found such things as cans of Pepsi that were thrown into the Mark Twain National Forest so long ago that the can was a steel one, not the aluminum that we use today.

But some places were remarkably clean. So clean that it seemed that they seemed untouched by humans. Check out this creek, it has water so clean that the fish and leaves appeared to be floating in space.

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Part of that, I think, is due to the concrete structures built at many of Missouri’s water crossings. They allow vehicles to drive over water rather than through it. And land owners seem to be protective of the water that goes through their properties. We commonly found razor wire lining trails and dirt roads set up in an effort to prevent people from ruining things. And one land owner came out to ask us to be careful.

Later in the day, we entered into the Mark Twain National Forest’s vast trails. The National Forest offers about 125 miles of trails and roads open to off-road vehicles. And these aren’t necessarily easy routes, either. There were some hairy rock climbs and grades on those trails. And once again, on a rainy day some of those trails would simply be impassible without chunky off-road tires at the bare minimum. I didn’t get many pictures of these trails as I was focusing hard on not blowing my $800 street tires on all of the sharp rocks.

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The Touareg did really well despite its issues. The four-wheel-drive system of this SUV kept it planted and the wheels turned with limited spinning. Some of the better prepared vehicles in our group had to claw their way up some of the hills that the Touareg tackled like it was a regular Sunday drive. And despite my Touareg being lowered, it didn’t scrape even once. I attribute that to the SUV’s short overhangs.

And the payoff was grand, as we soon found ourselves at the top of a mountain with a picturesque view. Admittedly, I forgot to turn on location tagging for my pictures, so I have no idea where it was taken. I think that we were still in the National Forest.

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After coming down the mountain we made one of our many trash cleanup stops. At this one, someone found a car battery. The damage to it suggests that it either fell off of a truck or someone chucked it. Either way, it made one good impact with the pavement before flying off into the woods. We think it was the former, because who throws batteries away into a forest? [Editor’s Note: Everyone knows that’s what the ocean is for! – JT] That’s a good core charge!

After finding the battery, we ended up at the Hodgson-Aid Mill, a historic grist mill on the U.S. National Register of Historic Places. Built in 1897, this mill was at least the second mill to be built on the property in history. It harnessed the power of the spring that it sits on for grain purposes as well as a sawmill. A post office and a general store were on the property, too, making it a center of commerce. It continued to be a mill until 1976, when it switched roles to become a tourist attraction.

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It was here that I noticed that something was wrong with my Touareg. The left rear tire seemed lower than all of the others. My suspicion of a leak was confirmed after a 20 minute drive into town. By that time, the tire was so low that at times, the sidewalls touched the ground. Crap.

Through some sleuthing with my ears, I found a leak to be coming from a very tiny rock that had embedded itself into a tread block. That rock, while small, was strong and long enough to puncture the tire. I estimated the leak was roughly 30 psi an hour, which was, you know, not good.

Since I was in the middle of nowhere, I went to the only store in town (a Dollar General) and bought two cans of Fix-A-Flat.

Breathtaking Camping

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The gooey stuff didn’t stop the leak, but it did slow it down enough that I was able to safely make it to camp. There, I found myself too distracted by Missouri’s beauty and I couldn’t fix the tire. Instead, I went swimming in a river and watched the sun set between the bluffs. To say that it was tranquil was an understatement.

When the sun finally went down and I got out of the water, I realized that something horrible had happened. My Touareg’s previous owner had upgraded the SUV’s wheels to big 20s, but didn’t upgrade the little 17-inch Vredestein Space Master to something bigger to match. The Vredestein Space Master is a cool little tire. When stowed away in the Touareg it’s compact, but with the help of an air compressor it expands to the full size of a stock tire.

It’s a neat bit of kit, but was more than a full inch shorter than the aftermarket 20s on my Touareg. On a front-wheel-drive or rear-wheel-drive car this is no big deal. You just mount the spare on the axle that isn’t driven. But a Touareg is full-time four-wheel-drive, so all wheels are drive wheels. This is really bad for a differential. In normal operation, a differential allows wheels to turn at different speeds, such as during turns. But it’s not meant to account for you running a big tire on one side and a small tire on the other. As this 21-year-old Deseret News article can tell you, being only slightly off can obliterate a differential in relatively few miles.

For me, this meant that The Space Master couldn’t be used, even just to limp my Touareg to a tire shop. That meant fixing it at camp. Thankfully, Gambler people are awesome, and someone gave me a tire plug kit. I eventually found two holes in that tire, both along the same expanse of tread. But within 10 minutes I had both holes reamed, plugs in place, and the tire was holding air like nothing happened. This was a bit of kit that I forgot to bring with me on this trip. I bet that I won’t forget again.

Camp is also where this Gambler proved to be vastly different from the ones of the past.

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Normally, people would be revving their engines to the high heavens all night doing drunken shenanigans. Camp is where I would see someone setting a car on fire, or someone ramming their car into the car that’s on fire. Camp is where someone had to get airlifted to a hospital after getting tossed out of a truck bed during a rollover.

None of that happened here. Things were so quiet that you could hear wildlife doing its thing.

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Sure, people still got plastered, but they decided to play volleyball or golf on the Ford Festiva’s roof rather than blowing up a car. Of course, there was still fire. A guy turned the horn of a trumpet into a flamethrower. But that flamethrower was used to melt aluminum cans (which were disposed of) rather than anything crazy. People ate, people chilled around campfires, and music played, albeit not too loudly.

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And as the proud Illinoian that I am, I gave poor unsuspecting people shots of malort. If you don’t know what malort is, it’s probably best described like drinking gasoline mixed with a burned condom. And even then, things were easy and fun. You didn’t feel like something bad was going to happen every other minute. I’d even say that this is the first Gambler in a very long time that I’d say was safe for kids and pets. It felt incredible.

On Sunday, my team set out again to hit more checkpoints with the goal of actually finishing the Gambler.

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This was also a rarity, as usually by Sunday everyone’s so tired out they just pack up and go home. I think the lack of crazy shenanigans attributed to that. On Sunday, we hit up more off-road trails and more of the Mark Twain National Forest.

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Along the way, we arrived at a cold spring that locals say is too cold for anyone to safely swim in. I jumped in…and found it to be warmer than Lake Michigan is most of the year. I don’t remember where this was, but I think that it was also in the Mark Twain National Forest. And golly, it sure was a great way to wash off all of that dust.

Funny enough, we happened upon a pretty clear river, too. And you bet I jumped right in! This was one of the last stops before the end of the rally, and I think it was a great conclusion to an epic event.

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Doing Some Good

In the end, Gamblers pulled out some 26 cubic yards of trash from the Missürburgring. The weight isn’t known yet, but I’m told that we filled up the two dumpsters provided for the event. People found everything from washers and dryers to refrigerators, car batteries, endless cans, and lots of furniture. Thankfully, nobody found a burned out RV or boat, but that’s a good thing. We like when the trash doesn’t include such horrors.

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As for damage, the Touareg made the nine-hour drive home no worse than it left, save for the tire plugs. And those were easily patched once I got back to civilization. My friends weren’t as lucky. The Toyota Sequoia in my group had a steering rack failure, requiring a very slow and difficult drive back to Indiana. There was an Oldsmobile wagon in my group too, but it didn’t even make it to Missouri before its rusty rear axle fell out from under the car after leaving a gas station. It seems most other people survived the event well; reports of damage included stuff like wheel bearings, fueling issues, and serpentine belts.

One of the last checkpoints was a brewery in the middle of nowhere.

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The Missourah Endurah

There, my friends and I reflected on the event, the past, and the future. And for my first real meal for the whole weekend, I enjoyed a fresh pizza with a sour beer. Over the course of the two days, we drove over 300 miles, with about 250 of them being entirely off-pavement. Maybe more?

Either way, I will be back to Missouri for its next run. If you’ve been holding back from attending these events because of something that you might have heard, come to Missouri, you’ll have the time of your life. I sure did.

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12 Responses

  1. It makes me happy to see a “proper” Gambler event. I lost interest after the first two Illinois gamblers, when it quickly devolved into all the debauchery in the camps. And they never did squat for cleaning things up either. This event is one I’d like to participate in.

  2. My 1985 300ZX (non-turbo) had a factory spare just like the one in the Touareg. It even came with a canister of compressed air.

    I am 99 percent sure that can had no air in it, and I would have been completely hooped had I blown a tire. But still, it was kinda cool.

  3. Judging by the vehicles I see at Gambler 500 races now.. they really need to change the name to adjust for inflation (Or put a cap on vehicle cost).

    I get the animosity between tho OG’s and the Influencer crowds at these events.

    Look what Burning Man has become.. almost the polar opposite of its original intention and now just a very expensive exclusive party.
    Gambler flipped that card five years ago.

    It used to be shitboxes, now it’s decorated $15,000 Subaru’s with snorkel kits.

    Still fun though if you can afford to get in and get over the prominent class disparity.

    1. That looks to be a first-gen Impreza with a snorkel made of plumbing pipe and a bucket, unless we’re talking about different cars. Sure some of the rides pictured look like they’re worth more than $500, but none of them exactly looked like high-dollar builds. They all look like either beaters, or beaters that were done up at home in the cheapest way possible.

      It’s hard to even find a runner for $500 nowadays, let alone one that would plausibly survive an off-road endurance rally. That Sequoia is one of the nicer, more capable-looking rides shown, and it destroyed its steering rack during the run. I’m not a Gambler, but from over here it looks like all the cars fit within the spirit of the event, at least. The one point I agree with is that $500 is an unrealistically low budget, but they seem to have solved that by just not really enforcing it.

      1. It’s my old 2000 Legacy GT 5-speed with a 2.0. Sold it for around $1500 a couple years ago. I had pretty much zero modifications to it. Really dig what the guy did with it, kind of jealous…

  4. I enjoy traditional off-roading and have had a ton of fun doing it. However, there’s something about seeing something that has no business off-roading attempting to off-road that is hilariously enjoyable.

  5. I didn’t realize Missouri even had a Gambler, let alone that it took place just an hour away from me. I would be tempted to join in next year, except that convincing my wife to let me buy a $500 beater (and actually park it in front of our house) might be more difficult than completing the actual course…

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