T​he First Florida Gambler 500

My first off road adventure and the very first Gambler 500 rally held in Florida.

1y ago

I went off-roading for the first time this year and it was an absolute blast thanks to an event called the Gambler 500.

By now I’m sure most car people have heard of the Gambler 500. If not, it is an informal rally on and off road started by Tate Morgan and friends in Oregon in 2014. The goal is to buy a cheap car that is impractical off-road, modify it as you see fit, and go have fun. There are minimal rules, but not being a dick and leaving the areas cleaner than you found them are the main ones.

T​his is not a good example of a vehicle that is impractical off-road.

T​his is not a good example of a vehicle that is impractical off-road.

F​orging a new Gambler

2019 was the first year for the Gambler 500 to come to Florida, specifically the Ocala National Forest which spans a good chunk of central Florida. Started and coordinated by Chris and Darla Hays along with a group of volunteers, the event was initially set to start at a motocross park just outside of Ocala until the number of people signing up quickly exceeded the space available.

Chris announced a couple of weeks before the start that he had potentially big news for everyone. That news ended up being that a much larger space was now available to everyone to park and camp thanks to the people at the “Hog Waller” mud bog/campground about an hour north of Ocala.

With this new venue set, the momentum continued to build as more people discovered the event and scrambled to find a cheap car to hack up. A few people actually bought cars the day before!

Sadly, we were not able to join the fun on the first day and showed up around 6 AM on Saturday. Chris, who had been up late welcoming everyone and pre-registering with his wife and the other volunteers, stumbled out to the gate half-asleep and told us where to find a spot and to not worry about registering until everyone else was up.

Following the quick and easy registration process for the Gambler and the camping spot, we checked out all the amazing cars and attended the driver’s meeting. What few rules there are were explained as well as an overview of the event and general advice. After this, we were free to go and given our set of GPS coordinates for the day.

I knew our car was not going to be much compared to the effort some people put into theirs, but I was blown away by all the amazing cars present. I’m sure we got some grumbles from people with cars about being in a Land Rover but hey, it was our cheapest option. Plus we had about $148,500 less into ours than the Keen rally car so that has to count for something.

On that note, let’s cover the vehicle that got my wife, our friends Richard and Blane, and I through this amazing event.

C​heap yes, impractical off-roader, not so much

My friend Richard works on Land Rovers as a hobby (and now as a full-time job at Euro Motors in Raleigh, NC) and always has a few parts rovers in the back yard. He had a 2004 Discovery that he got for a few hundred bucks with no suspension and a few other things missing. He sold a lot of parts off of it before finding out about the Gambler, but it still ran so that’s what we went with.

He did most of the work since I was busy working on other projects. The first step was replacing the missing suspension with a used lift kit. This was completely unnecessary but it was cheap and available. He also got an equally unnecessary bumper from a jeep for free and used just the plastic cover as our front bumper to ruffle some Land Rover purists feathers a little. A few more parts from the shed and it was time to tackle the appearance.

Richard is a massive fan of Jurassic Park so that left little choice as to the theme of the car, despite my efforts to hack it up. His wife, Bonnie, pitched in to add some hand painted touches while he installed JP vinyl and painted the wheels.

One of the things that he sold off the car was the transfer case shifter. He fixed this with some hardware store bits for the high/low and a 2’ long extension superglued to the center lock shifter.

My contribution was a skull to go on top of that 2’ extension and a rooftop sound system to play dinosaur sounds and music. I had a free 200W amp, a $4 200W 15” home theater subwoofer from Goodwill, a suitcase from a neighbor that I put a spare 10” woofer in, and a cheap surround satellite from that same neighbor for the highs.

All of this was run by the amp and fed by our phones with an absolutely brilliant result. It was incredibly loud outside and audible over the engine noise from inside the truck.

My other contribution, although I didn’t install it, was suggesting that we use those horrible bendy exhaust pipes from the parts store to fill the void where the cats used to be. This was a great, and also terrible, idea as they were super cheap but didn’t seal well and we no longer had a center console. A couple of wet towels stuffed in the shifter area helped, but we still had a shortage of fresh air while driving.

My friend Blane showed up from South Florida as I was getting ready to use a few fist fulls of zip ties to install some used eBay LEDs around the car as well as my old e28 grill. He was our official photographer and its obvious which pictures are his in this article. We slapped BMW and Mercedes badges on it and we were ready for a drive.

A quick test run through the gas station with dinosaur sounds at full blast confirmed it was ready to go.

Back to Saturday morning.

T​ime for Adventure!

We headed out right after the driver’s meeting with my wife, Chani, in charge of navigation. She told us where to go first and then proceeded to input every single set of coordinates for the day into the offline map app called Avenza.

Since she could see each checkpoint she added as a pin on the trail map in Avenza, she was able to take us in an order that made sense to her and led through a lot of trails other people didn’t seem to be using; for the Gambler or otherwise.

Because of this, we actually made it to a few more checkpoints than we would have and saved some gas/miles. This also meant going down trails barely wide enough for the massive Land Rover to fit, lots of deep sand, and no other Gamblers around to help should we need it.

Chani is an amazing navigator. Absolutely brilliant and we never got lost once. She was telling other people how to get places and made the whole experience so much better. Without her, we wouldn’t have gone to half the stuff we did. We covered 380 miles and only missed a handful of checkpoints each day. Getting lost is part of the fun, but not getting lost also has its benefits.

Y​ou knew this was coming

Luckily the Discovery was a champ. It never got stuck and it only had issues once at a busy intersection after about 2 hours of driving.

We started going in to limp mode because of the gear selector switch on the transmission which meant 3rd gear only. A burned arm and a few squirts of WD-40 took care of that for the rest of the weekend.

The other issue was it missing on two cylinders due to broken coil pack wires that were half-fixed by the previous owner. A fellow Gambler in an overheating Jeep next to us loaned us some wire so I didn’t have to cannibalize my sound system or lights.

The hour or so of downtime the first day was basically just a required thing for an adventure like this. We were prepared for much worse.

The only other problem was that we were too wide and too tall. After bashing the subwoofer against low hanging trees at least 20 times, knocking the spare into the roof, and losing a gas can, we stopped to flatten our profile a bit and used a trash tire we picked up as a shield. We still hit stuff, but it was better. We couldn't do anything about the width, so the truck continued to be filled with tree bits, inch worms, and spiders on a regular basis.

T​he driver also tends to favor their side of the car, so the passengers got a few more whacks in the face than the driver.

W​ho needs pavement?

Even though we were on our own or passing people going in the opposite direction for a lot of the weekend, we all had an absolute blast. I couldn’t believe how many trails there were and how far you could go without ever leaving the woods.

Every time we popped out onto a paved road for a few minutes we were surprised by where we were. We left pavement in North Florida and when we came back out we were 20 minutes from Daytona Beach.

We took turns driving but none of us wanted to relinquish the wheel. For four people with a combined off-road experience of close to nil (Blane being the only one with any at all), I think we did great. The Land Rover was definitely responsible for 80% of that skill though.

Play video

Winding Down

A​round noon on the second day, we met up with other Gambler's at a park for lunch served generously by one of the Gamblers. We got to see some cars we missed at the camp and went back to blasting around. At this point we were all used to driving on the trails, the bouncing around non-stop, the heat, the exhaust, and the dirt/trees in our eyes. I started to get that warm, tired feeling one gets towards the end of a great adventure and couldn't be happier about it.

It was an amazing experience with a group of awesome people who were all there to have fun and help each other out.

There were break downs, even a couple accidents, but no one was significantly injured as far as I know (I still have that burn mark) and a surprising amount of cars not only made it back to camp but got driven home. One Mercedes was driven 1400 miles back to Illinois and a Saturn was driven back to Indiana. Some of the Gambler cars are still being driven to work, around town, and to revisit the trails.

One couple from North Carolina pulled tons of trash from the woods with their ‘80s Ford station wagon. We passed them when they were loading a full-size couch on the roof. They ended up collecting couches, mattresses, tires, and a bunch of other gross crap left by the less desirable of humanity.


Although there was a report of one person being upset by our presence, the overwhelming response from the locals was one of gratitude and amused interest for this random group of crazy vehicles dashing about the woods collecting trash for a weekend.

E​verything was done through the proper channels and for such a large group of people, there was almost no drama at all which says a lot about the attitude of the Gambler.

Chris and Darla and the volunteers did such a great job that anyone who didn’t know it was the first event would assume they had been doing this for years.

P​hoto Credit: Chris & Darla Hays

P​hoto Credit: Chris & Darla Hays

I’m so thankful for them and for Tate for starting the OG Gambler because my entire life has been spent saying “When I get a car to this point I can take it to the track” or “When I have more money I can go do a crazy road trip in a beater or go do dumb stuff off road”.

This removes the excuse. Leave your perfectionism and excuses behind and just go do it. We made sure our car was reasonably safe with over 12 minutes of test driving and a quick visual inspection, but everything else didn’t matter.

As someone who does all their own work and is a recovering perfectionist, the Gambler 500 was the best form of vacation and therapy I could have. I didn’t care if something broke or if what we were doing was bad for the car. I just had fun and shared an unforgettable experience with some great people. Not a torque wrench or service manual in sight!

Besides a new found respect for my own Land Rover, here is what I learned for the next Gambler:

1. Get a less capable car

2. Don't bring as much stuff

3. Drive faster

4. Spend more time with groups

5. Get stuck

6​. Always opt for "The Devil's Butthole" routes

There are Gamblers all over; find the one nearest to you or start your own. Just go do it at least once.


Credit for the good photos goes to @blanealexanderphoto. A few were used from the group so if it's yours and you want credit let me know.

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Comments (11)

  • A fantastic report on a journey well enjoyed. Thanks for sharing!!

      1 year ago
  • I plan to make it next year. With a rally vintage BMW.. I had a schedule conflict this year.. Looks like a blast.. Thanks for the article.

      1 year ago
    • Join the facebook group, there is a smaller event happening later this year before the next 500.

        1 year ago
  • The trail was awesome & smooth, til this Honda Accord overshot its depth perception.. We got him out!! setting off his airbags... poor guy !! Good Timez

      1 year ago
  • Did you pick up any trash along the way?

      1 year ago
    • Yes! Two contractor bags of random stuff, a big mud tire, and the rear fender of an ATV and a battery haha.

        1 year ago
  • That looks like so much fun.

      1 year ago