The Gambler 500 – More Than Just Silly Vehicles Offroad

A Gambler 500 on a scooter? Pushing the envelope is something that I strive to do in most of my hobbies. I like taking a thing and seeing just where its limits are. In the past, I would modify iPhones to be waterproof long before that was a thing. I tried to invent a way to keep smartphones working in the dead of winter. Nowadays I bring that mentality to vehicles. After my beloved smart fortwo survived a car fire in 2016 and I picked up a second, I decided to put that little car through more than it was ever designed for, maybe to see just where its limits actually are. None of my tests compare to offroading..

The First Time


My first time offroading was actually in that little smart on the September edition of the 2018 Illinois Gambler 500. The car was rolling on all seasons and I’ve not had even a minute of actual offroad driving experience or training. All I brought to the table was the knowledge of how smarts work and how that could – in theory – make the car proficient off pavement. To the surprise of myself and many others, the little smart conquered the wilderness. It survived trails that killed actual offroad vehicles! That story will be in a post of its own.


With a successful Gambler under my dress belt, I decided I wanted to go even crazier for the 2019 Memorial Day run. But a smart is already bonkers enough, how do you get crazier from there? How about a scooter?

Upping the Challenge

Funny enough, I was supposed to ride a 150cc Chinese scooter for the 2018 Gambler, however I never got it ready in time and I ended up not riding it.


Most of it was because I wasn’t well versed enough in motorcycle repair to do the job right. Between you and me, I’m glad it didnt’t work out. If this never happened I would have never discovered how fun a smart is to offroad!

I decided to try again with a scooter in 2019. Nowadays I know a lot about motorcycle repair and I could actually get it to work. This time I would get a Japanese 150cc, preferably in bad-ish condition and for under $500. Almost two months before the Gambler I found the scooter. It was a 1986 Honda Elite 150D.


This scooter was rusty, it had a bent frame, it didn’t have a title, it was broken…it was perfect for this ride. Instead of allowing this scooter’s fate ultimately be getting into the hands of a scrapper, I decided to give it one last ride into Valhalla.

Time Crunch


In my previous entry I showed you how I got the scooter working electrically. Unfortunately the front tire was also worn down past the wear bars, so it had to go. Interestingly, getting a new tire mounted to the existing wheel would cost more than just buying a nearly new front tire already mounted to a wheel, so I did that. $50 to eBay and a few days later my wheel arrived in the mail.


Unfortunately, by this time the Gambler was literally just a couple days away and I had to not only mount this wheel, but sort out any remaining mechanical issues. Oh, and I haven’t even properly road tested the scooter.

That was on top of my daily’s brakes being completely roasted.

Getting to Work

The first thing I got out of the way was the road test. And with those couple days remaining I learned that the cooling system had a mind of its own. It leaked coolant, the radiator fan didn’t work, and I had no idea if the thermostat even worked. Unfortunately a thermostat would have taken a week to ship, same with a thermoswitch for the radiator fan. The carb was also kinda sorta clogged. I felt a lot like Jalopnik’s David Tracy, staring down an impossible problem with no time to fix it.


I decided to ignore the carb as I had a top speed of 65 mph. Then I moved to the cooling system. It was actually impossible to get the thermostat and thermoswitch in time, so I decided to just hope everything worked as they should. To combat the loss of the cooling fan, I was able to same-day ship an oversized fan for a 250cc scooter. I installed the fan that night and crossed my fingers it was going to be enough for a 500 mile pounding offroad.


The 2019 Southern Illinois Gambler 500 Memorial Day Run

The morning of my trip down south was absolutely hectic. The scooter still had the worn front wheel installed, I hadn’t packed a single thing, my trailer wasn’t ready…and I had to meet up with my caravan at noon.

Surprisingly, for the first time I’d ever take the wheel off a motorcycle/scooter, I was pretty proficient at the wheel swap. Before I knew it, I had the wheel swapped, the trailer prepped, and my car loaded with gear. Then I took off for the best weekend of my entire life.


The smart further proved itself to be an amazing vehicle hauling that scooter for a straight six hours, most of them with the foot to the floor battling a stiff headwind. Fuel economy was a respectable 30 when I wasn’t dealing with headwinds and an unfortunate 22 when I had my foot to the floor.


We arrived at the start point early in the evening and it was instantly amazing. It felt like a family reunion as we reunited with familiar faces and greeted new ones. We then admired each others’ vehicles, cracked open a can of beer, and started the party before the party.

Photo Credit: Dahlia-Brandon Boyer

Some amazing rides showed up from clean Rangers to this amazing and extremely dangerous Miata Death Kart. And yes, it is road legal.

Photo Credit: Amy Hedman

Trial Run

Thankfully I decided to try offroading the Honda. I got it offloaded, hooked everything up, then went for a ride. This particular Gambler wasn’t setup like a normal Gambler. Instead of the starting point being just that, the start point was actually home base. And this home base? Hillbillie Offroad. It was a massive offroad park with miles of trails and over 1000 acres of offroading.

Photo Credit: Greg DeLong

Gambler 500 rallies are usually one way navigational rallies from point to point, but this one was different. This rally had various stages and when you were finished with each stage, you can go to the next or come back to base. Little did I know this would come to my benefit the very next day.

A First Time for Everything

My ride around Hillbillie was my first time ever offroading on two wheels. Yep, I was about to ride 500 miles offroad on a scooter with street tires and I haven’t even ridden a single mile offroad before. It took maybe ten minutes for me to discover that this was maybe a bad choice…

I rode into the first trail on the property and it was immediately challenging. The entrance was a 30+% downgrade down unstable rocks and mud. After I somehow got down that I was greeted to two feet deep mud leading into a two feet deep water crossing. The scooter had met its match and it wasn’t even the first day yet. I was too afraid to cross the water, but the way back out of the trail was far too steep for me to make it up on my own.

Eventually a teammate with an AWD Suzuki Aerio and another with a Ke$ha themed Cobalt appeared on scene.

Photo Credit: Jeremy Drowns

The Suzuki crossed the deep mud and water without issue, the Cobalt blew a hole into its oil pan crashing into a rock. Not even close to the first day and now there are two vehicles seemingly out for the count.

Our friend in the Suzuki first saved the scooter, helping me walk it back up to higher ground. While trying to push the scooter up the hill it came down it stopped starting. My diagnosis later that night was that the LED spotlights, the external cooling fan, the existing halogen headlight, and my USB hub all overpowered the 80s scooter’s electrical system. But before I could fix that I hopped in the Suzuki and went along for the ride to rescue the Cobalt. With the help of some straps and liberal application of wide open throttle, the Cobalt managed to get away from the clutches of death despite leaking almost all of its oil.

Jerseyville, We’ve had a Problem

As if working my own mini-Apollo 13 problem, I decided to save the scooter’s electrical system by killing the halogen headlight, killing the USB hub, and only running the spotlights with the fan. After a quick charge on the battery this turned out to be a winning combination. Upon getting the scooter’s electrical system stabilized, I learned the scooter no longer started without starting fluid and even when it was running at running temp it would not idle without dying. Suddenly that carb issue I decided to ignore was seemingly advancing. If only these were going to be my only problems.

Later in the night and still before the first actual day, the scooter stopped starting. It turned over but even with heavy use of starting fluid, nothing. It wouldn’t even choke or cough. I spent most of the night on the skidpad watching cars turn tires into smoke and trucks pull each other, thinking about what could be wrong with the scooter. At some point I got frustrated enough that I walked up to the scooter and in a fit of unhappiness, ripped off all of its panels. Swapping the spark plug, coil, or CDI unit did nothing. The scooter somehow didn’t have spark. It just wouldn’t start. I was ready to give up and give the smart an unexpected round two the next morning.


When the sun rose I immediately got to working on the scooter again. I thought about the last thing I did when the scooter was running and I remembered that I hit the kill switch. Hmmm…maybe that’s it? Maybe the kill switch somehow went bad? Worth a shot! I shot carb cleaner into the kill switch and sure enough, the scooter started when I gave it a try.

A True Gamble


Alrighty then. So I have leaky coolant, an engine that won’t start without starting fluid, a cooling system that I’m not even sure works, a death wobble at nearly any speed, no way to charge my devices on the road, and now a start/stop switch that’s hungry for carb cleaner? What else could go wrong?

In one last attempt to wring out issues, I took the scooter on a top speed run on the roads outside of camp. 65 mph top speed and the coolant temperatures stayed near the red, but otherwise in the safe ranges. Considering the high for the day was going to be 100 this wasn’t ideal, but it was going to have to work. Whatever that problem was, I wasn’t going to find out at Hillbillie.

Off to Roads Unknown

Photo Credit: Amy Hedman

Our convoy set out for the first stage, a hundred mile run to a bridge to nowhere. I strapped a two gallon jerry can to the rear of the scooter, packed up some basic tools, grabbed my jug of coolant, set my tunes, then hoped for the best.

The first part of offroading was easy. The scooter maintained a temp and speed on the gravel roads surrounding Jersey County. I was even passing other Gambler cars, on a scooter with street tires with a rider that hasn’t ridden more than a half mile offroad. It didn’t take too long for the gravel roads to turn into dirt roads and for the dirt roads to turn into muddy roads.

It got Even Harder

Sure enough, eventually we encountered the same kind of deep mud that scared me off the night before. The cars in our group with street tires turned around and headed back to camp, but me? I didn’t come here just to chicken out. While the Cobalt stuffed itself into a rut, I twisted the throttle, stuck out my legs like outriggers, and made it across the slop. Within minutes, the rest of my team caught up and we surged forward. Despite warnings that the mud was going to get worse ahead, I followed.

It very much got worse. My shoes were just blocks of mud and the scooter was up to the floorboards in muck. Despite that, the scooter plowed forward.

Just when I got comfortable with the mud, we came up on a water crossing. The Suzuki and the Cobalt crossed with the water definitely getting to a level that was far too unsafe for the scooter. Looking where I wanted to go, I noticed there wasn’t a single away around the water crossing, I HAD to do it. I found myself regretting not installing a snorkel. But as many Gamblers will say when facing a possibility of not making an obstacle, I decided to send it.

Going Swimming

I splashed into the rocky water crossing around 10mph then cranked the throttle. As I rode I felt the water get up to my knees (well above the air box’s opening) but I tried not paying attention. I kept the throttle pinned and focused on getting to the other side. To my amazement the scooter actually did it. We crossed deep water without a snorkel and it somehow didn’t hydrolock! I began to tell myself the scooter was unstoppable. It very nearly was!


The mud eventually turned to curving country roads, the country roads turned into sandy forest trails with difficult terrain. We witnessed trucks get stuck, but our crew of unfit offroaders kept going. Unfortunately, these trails are where I would have my first ever motorcycle crash.

Photo Credit: Oscar Mata

I was riding on the forest trail/road somehow consisting of extremely loose sand (or something like it?). It was like riding on ice. However, so long as I kept a slow pace it was okay. Unfortunately, my team didn’t notice my slowing down and they basically kept full speed ahead.

This trail loved taking Gamblers hostage

Getting the First one out of the Way

To catch up (and to ease my nerves) I decided to ride on the sides of the trail, which consisted of dirt and grass that I could get much more speed with. Well, at some point those grassy sides narrowed to just a couple feet wide with the sand to one side and trees to the other. At some point, the grass was no longer level with the sandy center. This wasn’t a problem until I encountered a rocky, rutty portion of the trail where the grass I was riding on had a 10ft drop down into the ruts below. I target fixated and at roughly 15-20mph I rode off the grass and ten feet down into the rocks.

Before the scooter made contact with the rocks below I jumped off. My hands (wearing cheap $10 gloves) and my left knee took the entirety of the fall. Hands were fine (gloves only got light scratching) but my knee was bleeding. Well, a dress and yoga pants definitely aren’t good riding gear! The front wheel broke most of the scooter’s fall, with the dashboard taking the rest of the force, breaking the windshield and taking out both mirrors.

Brushing the Dirt off Myself

In picking up the scooter from the fall it presented another new problem: It was awfully tappety. I’m not sure if it was overheating or what, but while the engine would “start”, it sounded like it was eating itself alive and it had no power. I assumed it was simply overheating from heat soak. After all, I rode the thing right next to and sometimes inside the hot mark for almost 100 miles now.

After letting it cool for five minutes we were back on the road. We crossed the first hundred miles and the ending of the first stage. Unfortunately, I never got pictures of this as I had to give the scooter constant throttle to keep it from dying. And as the ride soldiered on, the scooter seemed less willing to start again. The switches were also deteriorating from the carb cleaner. But even as the scooter was crippled it continued to fight.

Eventually the hardcore trails ended and opened up to easier to ride dirt roads, or so I thought. While racing to the next checkpoint and drafting the car in front of me on a paved road, the road suddenly became not-paved. But worse than that, the transition wasn’t simply to dirt, it was to very very loose rocks.

An Unforgettable Near Death Experience

I hit the transition at 60mph and in an instant, the scooter’s rear end broke into a high speed slide. Here I was, wearing a cheap Chinese helmet in a dress and leggings. I stupidly left my real gear at home. At some point it felt like the rear wheel was perpendicular to the front. I started thinking about how to crash or what to crash into for the best survival. My teammates cleared a path for me.

Taking a deep breath, I very gently and slowly rolled off the throttle. Eventually the rear wheel safely caught traction and in doing so caused a death wobble on the front wheel. I could deal with the death wobble since the front end was so light, I was just thankful I was able to recover what everyone thought was unrecoverable. Vibrations during the slide were so great I lost a few more parts of my windscreen and my mirror glass, but I wasn’t about to complain.

We continued onward to the second checkpoint. We had to take a bunch of detours and even rescue a Jeep due to the massive local flooding. Some trails were absolutely impassible, even in vehicles with snorkels.


Along the way the scooter kept blowing minds. Here the little Honda was, deep in the wilderness hundreds of miles away from any city, and it was hanging with purpose-built offroad vehicles. And here I was, someone that has never ridden offroad before and I was making it look easy.

The Scooter Throws in the Towel

After finishing the second stage we turned back and headed back for camp. At 70 mph on well paved roads, all of a sudden the engine started dying. I pulled out starting fluid and shot it into the carb hoping maybe there was a hiccup. There wasn’t. The engine was shutting down whether I liked it or not. Starting fluid only delayed the inevitable.

We pulled over to the side of the road where the scooter finally gave up. It was smoking, the engine was tappety, and the buttons didn’t work. It seems I killed the scooter. I checked the odometer’s trip, it showed 170 miles, 200 miles since I unloaded the scooter off the trailer.

Photo Credit: Dahlia-Brandon Boyer

As my luck would have it, a Ford Ranger painted like the Pizza Planet truck happened to be passing by and we flagged them down for help. We shoved the Honda into the back of the truck and sent it home to camp. I finished out the ride on that stage in our team’s Kesha Cobalt.

Back to the Lab


Back at camp I tried my best to revive the poor little scooter but it was to no avail. A new CDI, coil or plug could revive it. It would fire on starting fluid, but die as soon as it ran out of it. I adjusted the valves to no success. At least the scooter firing on starting fluid narrowed down my issues to likely being fuel related. Unfortunately, I didn’t bring a spare carb and I didn’t have anything to clean the existing carb. I should have replaced or cleaned the carb before the trip and now I am facing the consequences of my poor preparation.

That can only mean one thing:

Time for the smart to Come out to Play.


The smart’s first act being released into the Gambler was participating in the tug of war battles on the skidpad. I paired against a wild Zombieland themed Ford Festiva and honestly I was feeling like I’d be the loser.

Photo Credit: Ty Eller

Here I was in a little three cylinder city car with a misfire, transmission and clutch with nearly 160,000 miles, worn tyres, and sitting in water. Meanwhile, the Festiva was sitting on fresh parts. Oh well, I sent it anyway. To my surprise, as the Festiva converted its tires into smoke the smart pulled it across the pad with ease!

My Next Challenge: Pull Some Men


The strongest guys would all try to overpower the little smart’s 68 pounds of torque, numbers of men increasing every time I beat them. Not even ten of the strongest guys on hand could stop me from pulling them across the pad.

Cranking it to Eleven

The smart’s final shenanigan for Saturday night was going up against a Chevy Malibu and a Dodge Ram in a tug battle. The Malibu was a near equal match but it ultimately pulled me away. I didn’t stand a chance against the Ram and I definitely burned away a lot of clutch trying in a futile effort. The Malibu and the smart got a picture together before the Malibu was ultimately drowned.

Photo Credit: Jim Hinkle

Surprisingly, tug battles were hardly the only shenanigans on the pad that day. Anyone with enough power to break their wheels loose did burnouts. And yes, that flag says “no step on snek”.

Photo Credit: Dahlia-Brandon Boyer

Small cars spun like tops in the water, and our crowd favorite Miata death kart made several appearances.

Photo Credit: Dahlia-Brandon Boyer

Towards the end of a Gambler some cars may be too far gone to drive home. In these cases, some venues are happy to take your dying car, provided you have your title on hand. If the car’s incredibly far gone, sometimes it’ll be finished off by being driven hard, almost Cash for Clunkers style. One of the cars putting up the biggest fight on this run was a former police Crown Victoria. It was hanging on by a thread and it was thought it would die almost immediately. Somehow, after at least ten minutes wringing on the machine it held on.

Photo Credit: Charlie Miller

We all gathered around the unstoppable Crown Victoria as it simply failed to die. At one point, the engine started misfiring in such an odd manner that it sounded like an EDM music beat. The whole crowd started dancing like a club. Then all of a sudden, fire!

Photo Credit: James Nussbaum

That Wasn’t Supposed to Happen..

The car started going up in flames. Unfortunately it burned too strong and the fire extinguishers on hand couldn’t handle it. It was decided to let it burn out and call the fire department if necessary. Oh, burn down it did…

Photo Credit: Kenny Davis

The fire department was called at some point and they showed up towards the end of the car’s burn. They took little time in finishing off the fire and after they secured the car to make sure fire wouldn’t flare up again, the crazy fun at camp continued. Thanks to the local fire department for securing the area!

(Note: While finishing off an already dead car is one thing, we do not want to start fires.)

I did actually achieve in killing one car. I launched a Chevy Malibu off a jump then sent it to a muddy water grave.


The car did start later in the day but it ultimately seized soon after because of my execution. My prize for killing the car was a bruise that went all the way around that actually left a really faint scar behind.

But Wait, There’s More!

The “MVP” of my attempted car destroying spree was a little AWD Suzuki Aerio. Despite our best work, the little thing just wouldn’t die. We jumped it, we sank it in mud, we crashed it into other cars, we even yanked its doors off but the car just wouldn’t die.


Amusingly, my effort in trying to kill this car was where I discovered that deep mud puddles in a dress is absolute heaven. I…I never thought I’d ever say that in my entire life.

The next day was all just that. We wheeled around in our cars and strengthening our bonds with each other.

The Suzuki was eventually brought down, but not before it was cleared for takeoff.

My worn out smart with equally worn out all season rubber continued to blow minds and create smiles. I know smart’s engineers never designed the car for what I used it for, but it’s amazingly proficient at the job.


It went everywhere but the deepest mud pits. It seems the lack of a front and rear end really helps it crawl around. The short wheelbase also seems to make up for the lack of ride height.


The Hidden Beauty of a Gambler 500

Photo Credit: Kewanee Gambler 500 Rally Team

Some may think the Gambler 500 is only about taking impractical cars and abusing them to within an inch of their lives offroad. To some possible surprise, that assumption would be wrong! I’m a very openly trans person. I’ve learned the hard way that this can limit what groups you’re welcome in. Even if you are allowed in a group there’s no guarantee the others will even acknowledge that you exist. Even ignoring that aspect of life, it may not be super easy to find a place where you feel you truly belong.

Admittedly, I was scared I wouldn’t be accepted in the Gambler community. I had all the stereotypes in my head about the kinds of people that would take oddball cars and go mudding with them in the backwoods. And how could I – a seemingly delicate, extremely feminine, and unapologetic trans woman – fit in? The September 2018 Gambler 500 taught me just how amazingly inclusive this community is. I’ve never cried as much from feeling a part of a community as I have with this event. Here you have everyone from every walk of life coming together for one seriously fun cause. Have fun on trails, pick up trash, and promote local motorsports. Some Gamblers are from the city, some from the country, some left, some right, Gamblers are everyone.

The Memorial Day run further cemented this as I made new awesome friends and more. We all became a part of a huge family. Some say blood is thicker than water but if anything, a Gambler 500 rally challenges that notion with nothing but love, fun, and a level of togetherness you’ll never experience anywhere else.

Newfound Love

I had so much fun I became a fan of a few more things I never thought I would. I gained a massive appreciation for pickup trucks, fell further in love with offroading, and I felt my love for city living dwindling away. It wasn’t even a month after the Gambler before I picked up a new to me Ford Ranger and as we would say…SENT IT!


Late in the final night those of us still left around decided to have one big party to blow it out. Everyone still with a working vehicle converted rubber into smoke, more tug battles, and sharing our awesome stories of the weekend. Some of us even started planning for the next event. Others actually managed to change Subaru clutches without an engine hoist! I made new best friends that night and honestly never felt more at home at an event.

Photo Credit: Vanessa Vega

On the drive home I couldn’t believe the weekend I had. This event was the best weekend of my life by far and I started counting down the days until I could do it again.


Even better, I gained so many awesome friends that I love so much and have shown me the kind of friendship I’ve been missing for so long. On the outside it seems the Gambler 500 is just a bunch of drunken crazy people in the woods, but the reality is so much more.

So grab a cheap car, put some equally cheap all terrains on it, grab a friend, and have a weekend of a lifetime.

Photo Credit: Dahlia-Brandon Boyer

15 thoughts on “The Gambler 500 – More Than Just Silly Vehicles Offroad”

  1. IDK where I got the link, but I loved this story, and the the other one I read so far about the Gambler 500. Still not totally sure what that is, but sounds like a good time.
    You got pretty far on that scooter even after it has shown that it was ready to be put down. !

    I could visualize you on the scooter ‘send it!’. Great mental picture.


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