Outlaw 100: An Extreme Race For Pain Seekers

Give Me The Fish (GMTF):  Outlaw 100, is a 100-mile race with the option to strive for 135 miles in Robbers Cave, Oklahoma. It’s is a come to Jesus race that will make you face your inner demons and come out the other side. Highly recommended for adventurers, pain seekers, and runners.

“So, why are you doing this?”, I asked as we both struggle up this mountainside/borderline cliff. “Oh, I don’t know. I just do.”

We are both 20 miles into a 135-mile race for him and a 100-mile race for me. On a course called the Outlaw 100. The race was founded the year or two prior with only 5 finishers for the 100-mile distance, 3 of which are triple crown competitors (or so, I’m told). Which if you are not a real runner, like me, it’s a series of ultramarathon races across relatively rough terrain. In other words, hard-ass courses.

The Outlaw 100 is in a section of Oklahoma I didn’t even know existed. It’s full of a mix of swamps, mountains, and what I was also told by the locals, Alligators among other dangerous wildlife. The course is a set of two loops, a 7-mile loop, and a 13-mile loop. Both of which you can do 5 times to equal a 100-mile course, for the main event, but also consists of a 135-mile course, and a couple of shorter distances, which you can down select to at any point as long as you don’t place.

I would argue that this is less of an ultramarathon course and more of an adventure race which consists of water wading, borderline cliff climbing and trails with stones the size of your fists. All spanning an elevation change of nearly 9,000 feet.

If this still doesn’t seem hard enough, the area is soaking wet with mud and standing water on almost every section sometimes sinking well above our shoes and in 40-degree weather (it was warmer during the day).

To say this is a grueling race is a bit of an understatement. In the first year of the race, the fastest time was 29 hours, which for most 100 milers, is crazy saying the goal for a decent runner is typically under 24 hours.

Needless to say, the Outlaw 100 is a come to Jesus race, and if you are a pain seeker, it’s the place to be.

What Led Me To The Outlaw 100

If you don’t know at this point. I would not call myself a serious runner by any means. I try to run a couple of times a week, and really just wanted to knock out a 100-mile course as a bucket list item. I had started training in July the year prior. With a plan to knock out a 50 miler at the end of September and run a 100 miler at the end of November.

Unfortunately, I got a stress fracture during the 50 miler I did at mile 30, still managing to finish, but jacked myself up enough to be on crutches. So, I decided that I would rest through November, train in December (technically I was told to not run for 8-12 weeks), travel to Chile in January and race in February. The Outlaw 100 was the next most feasible race.

Not being smart enough to read about it before I started, I just signed up and didn’t look up anything about the race until a few days before. I probably should have also got the hint when I looked up the race times and almost all of the race categories were blank (not enough people finished).

When I did finally look up the Outlaw 100, I realized that I had already bought a plane ticket that left 30 hours after the start of my race and the cut off time was 48 hours after the start.

But, at this point, tickets were bought, the rental car was booked, and I was locked in. So, off to Oklahoma I went, needing to get close to a race record to catch my ride back and overwhelmingly underprepared.

Arrival At Robbers Cave State Park, Home of The Outlaw 100

After flying into Fort Smith, Arkansas, getting a car, and driving the hour and a half to get to the Outlaw 100 race site, I checked in with a friendly staff, grabbed the typical bag of running “goodies” and took instructions on where I could sleep (they have heated bunkhouses for $10 a night).

 It was pretty late at this point, so I grab my bags and headed to the bunkhouse. There were a few other racers there.

Of those there, one was a guy who had done something over a dozen 100 milers, who said he normally averaged sub 19-hour runs. There was a couple of girls who were running the 50-miler, one pacer (a friend of the first guy), and a guy who had run the Outlaw 100 the year before but haddown selected to complete the 50 miler at mile 80.

 They’re all extremely friendly, and all talk about the race. You could tell that everyone the room was nervous, maybe a little excited, and talking about everything they heard about the year prior, or talking about their experiences when they ran the outlaw 100 the year before. 

I, like usual, had by far the least amount of experience running ultramarathons. But, you know, whatever. 

Everyone is happy to share advice. But, at the end of the day, I realize it’s like everything else, most of the stuff is so personal to them that it’s borderline worthless for everyone else.

Still interesting to hearing, especially about the past races they had done, to include one guy that is known as a “dirtbag runner”, because he traveled around the US and the world following races, volunteering, and running.

 *He has a blog if you want to check it out.

 After we all got kind of tired and realized that we had to be up at 5:00 the next day we all racked out.

Pounding The Trail, Literally

The next day was pretty straightforward, get up, pack up sleeping bags, put my drop bag at the start of the race, snap a few pictures, and we are off.

 Like most of these kinds of races, there are only maybe 30 some runners at the start. 

 The second we start, I realize how pitch black it is. The next second passes, and I realize that I had grabbed the wrong headlamp, this one was supposed to be my alternate.  

 Why does this matter? 

Because the one I grabbed sucks. 

I can’t even get it to the light 3 ft in front of me. So once again repeating the same mistake as I made on the 50 mile Overlook Endurance Run, I’m running on crappy terrain without light.  

 I soon find out the trail is so rocky, that it’s pounding through my minimalist shoes. I’m only a couple of miles in and I can already feel the bruises forming on my feet. 

 To avoid this, I’m trying to use other people’s lights by running behind them and trying to leap over whatever they are, but that’s not working very well. 

 I soon realize I’m only 7 miles in to this Outlaw 100 race, and my feet are already bruised, hurting, and  soaked 200 times over.

All seemed per the usual.

But, besides that, the course is beautiful you can almost forget the pain for a second as the sun starts coming up across the water. In some ways, I’m kind of thankful that I was so slow because at one point we get to a cliff that I literally have to climb down. A cliff I don’t really want to think about climbing down in the dark. 

I’m also realizing I’m going to have to do this a few more times to include in the pitch black when I’m tired the following night.

 But nothing to do, but just to keep running.

The Badasses Of The Trail

 At some point I meet up with a couple of guys that are seasoned ultramarathon runners. 

In most places when you meet strangers, you might exchange a few words and then move on, but we have up to 48 hours to kill. So, here, when you meet people, you learn everything. 

 They all seem to own businesses, be high proficient tradespeople, or other successful individuals.

Like usual, it seems to be that the hardest things attract the people that want the most out of life.  

One was exceptionally inspirational, he had a drug habit that was wrecking his life and 5 years prior, he finally decided to pull his act together, and one of the ways he got over it was by starting to run. 

As he pushed himself, he reached longer and longer distances until eventually, he was in the ultramarathon field. For him, whether it was the pain or the accomplishments, running pulled him out of the hole he had dug.

And to top it off, he ran in sandals. 

He swore they were built for running (you can find them here), but it was still kind of interesting to see him running down the course in a pair of sandals that looked like a pair of thick flip-flops with a back while wearing a pair of thick wool socks. 

Finding My Tribe

 As the miles tick by, whether it’s because we’re in different places in our heads, or just want a little separation, the runners that I ran with would always separate apart either one of us going ahead or falling behind.  

 But, it always seemed you would find somebody else, and usually, just the right person to keep you going.

 As we’re scrambling over these rocks of death, waiting through the supposed only two water crossings, I met two more runners.

 Side note, they only count them as river crossings if it’s above mid-thigh. 

So, two river crossings? Yeah, ok, whatever you say.

Of these two runners, one was a super-smart Asian dude. VP of a company, and a nice dude, but as is stereotypical, he was hard to understand, but all the better for passing times on the trail. 

His running partner was a man with a deep Oklahoma accent and a well-respected traveling welder in his field.

 The first guy was planning on doing 135 miles, this was definitely not his first ultramarathon. The other was more relatable, and kind of in the same shoes as me. He had prepared more but this was also his first 100-miler and first time on this course.

 Together we did the typical ultramarathon run-walk-repeat methodology.

But, as the race goes on, it becomes so easy just to keep walking and not start the run part. But, having a solid tribe at your side to help kick you in the ass helps everyone move forward.

At one point or another, we would all be walking and one of us would just start running again, and it was that drive to keep up with the pack that kept us all going. 

 Those two men helped carry me forward. While my feet seem to hurt more and more, threatening game over, the constant banter and the blunt honesty kept me going.

 Finding The Pain Barrier

 Mile after a mile, my feet slowly started to lose their ability to bend, I started feeling like I was walking on stumps around mile 30.  I tried duct taping my feet, wearing multiple socks, and just forcing my feet to go numb. But, they just stopped working. 

The interesting thing was, I wasn’t tired. Sure, I was a little drained, but my body was still good. 

It was just the unbearable pain, at around the 17-hour mark I was starting to realize that I was not going to make it through all 100 miles of this race.

 I’ve always prided myself and being able to push through the pain. Looking for the hardest task, finding what my breaking point is and shoving my way through. But I’m not going to lie, I found it on this race.

The Outlaw 100 got me.

 I found my pain threshold, well at least the threshold without having inspiration by desperation. 

 Around mile 45, I told the other two to go ahead. There was no way I was going to be able to keep up, the pain was shooting at my legs now I was in sheer agony. 

 I slowly stumbled my way to mile 52.4 (the finish/start) and stop the time at around the 19-hour mark.

 I went to the Outlaw 100 race director and told him that; that was it for me. This was one of the hardest things I’ve ever done and I had to admit that I couldn’t make it. They hand me my 50 mile buckle and I dragged myself to my cabin and pass out.

At this point, the only Brightside I see is that at least I’ll make my plane.

  Aftermath Of The Outlaw 100

 Waking up the next day, with my feet still feeling like blocks, looking like purple crayons and throbbing, I packed my stuff up and slowly made my way to my car.

 All I got to say is thank God for cruise control and emergency hand brakes. With what’s probably less than legal driving methods I made it back to the airport and onto the plane to make it home.

Of course, I’m upset I didn’t make it, and more upset to find out that my two companions didn’t make it either, but I have no regrets about the race. I hung out with a series of red-blooded individuals that want to do something with their lives and had an adventure that I could not have had anywhere else. 

 An adventure that had everything that an adventure should have, new places, new people, a new experience, all while meeting the uncomfortable and finding my limits. 

 My limits, I now know has something to do with minimalist shoes on rocky trails, and finding out that foot torture is definitely a weakness of mine.

 But, I will be back. Not just to win the race, but to push past a new barrier.

Update: Completed On 2nd Attempt!

After wrapping up the race in 2020, it was heavy on my soul that I hadn’t finished the race. I’m not going to lie, I did not keep running when I finished. I actually went right back to powerlifting and putting on the weight I had lost, topping out at 190 and hitting some Squat PRs at 345.

But, I hadn’t lost sight, around October I started ramping back up.

It wasn’t easy, but I managed to get in weeks ranging up to 75 miles. And they were all feeling pretty good.

Then, 4 weeks out from race day, I had a partial Achilles tendon rupture.

But, with some dedicated recovery and focus, I managed to make it to race day. 

2021 was a brutal year on the course. A winter storm warning blew through and the majority of participants backed out.

The race spanned the gauntlet with temperatures dropping down to -15 degrees and 4-5 inches of snow, but somehow I managed to finish and even took 2nd due to the mass amount of people failing to finish.

Hell of a race and couldn’t be happier with my finish.

 If you have any questions about the race, whether out of curiosity or because you have plans to run it the next year, feel free to ask me in the comments.