A Weekend in Stillwater, Oklahoma at the Land Run 100

Mud. It’s hell. A catalyst for catastrophe and the end game for any bike event. Honestly, it’s been the one thing grating at my conscious since first accepting the invitation to the Land Run 100 late last year. For six years now, Land Run 100 has been put together by Bobby Wintle and the team at District Bicycles in Stillwater, Oklahoma. It’s a challenging race on a challenging course, yet the entrants must adjust their own psyche to determine what mental state they will choose to enter these dirt roads. Be it personal grit, the desire to complete the course in its entirety, glory, or to be the fastest group of racers in one of many categories. Racers register for the event to conquer their own goals.

The story of competition is as old as the ages, yet the history of the Land Run was one formed long before the existence of dirt roads as we know them today.


As is it written, imagined, or recorded, History with a capital H is subjective. For whom was it written, or to, and once this is established, how are specific events recorded? This, historically, has been what makes our education so contrived, so controlled, and ultimately, so constructed. The 1889 Land Run went down two ways, depending on how you look at it. One side of the coin depicts free land, opened to settlers, those white immigrants from across the great sea, handed down from men in offices with quill pens and paper. On the other side, the natives, who learned ages ago how to live symbiotically with the land their forefathers and mothers had inhabited. One side believed in respecting and honoring nature, the other, chose to control and overrun it. The history of Land Run is the same as the history of the United States.

In 1879, white men, the “sooners” or “boomers” or whatever you prefer to refer to this group, demanded land. They demanded entrance into the territory now referred to as Oklahoma. They were told it was illegal, yet they settled anyway by setting up shanty towns made from tents. In fact, it wasn’t until 1889 that cannon fire marked the free-for-all Land Run, allowing anyone to claim their own parcel of the 1,887,796 acres, in 1/4 mile by 1/4 mile squares. Soon, this once vast and seemingly empty land was drawn and quartered into city grids and property. Towns popped up – including Stillwater, Guthrie, Oklahoma City – and the whole thing was deemed a success, prompting more of the American West to be settled in a similar manner.

By 1850, Native Americans were already removed from these lands, forced to sell and accept meager compensations. Soon, the “Indian Territories” shrank more and more, resulting in near eradication. Come 1889 – the year of the Land Run – and they were long gone from what is now known as Oklahoma. You can thank Andrew Jackson for that. In 1830, he created the Indian Removal Act. Later in 1887, it became legal for the Federal Government to divvy up Tribal Lands, just two years prior to the 1889 Land Run.

This information is all compiled in a free zine handed out at Land Run as both an educational piece for entrants and a reminder that this land belonged to others before white men ever took a step on what we now call North America.

The Land Run 100

It might seem gauche to name a bicycle race after the divvying of tribal lands, but it is historically relevant to the vernacular of the area. Those 1/4 mile by 1/4 mile parcels still exist today and in between, there are roads, many of which are still covered in the rich, red dirt the event is known for. Add spring rains to the mix and you’ve got mud. Not just any mud, either. Derailleur destroying, brake failing, carbon-eating, steel corroding mud, mixed with sand and tears. Mud redder than the bloodshed on these very lands and mud that will have you second guess riding a bike when the storm clouds loom overhead.

This infamous experience draws people of a certain grit, a grain coarse enough to roll through the slop, past the internal doubts, the muscle cramps, and mechanical failures, to trek, traverse and crawl their way through the red abyss and across the finish line. All to get a hug from the organizer himself, Bobby Wintle.

Bobby’s life in the Stillwater cycling community began with District Bicycles. From this shop, he brought in cyclists from all over to show them the magical riding surrounding Stillwater. Soon, he decided to throw a race and the Land Run was born.


Luckily, for us and the 1400+ other entrants, this year’s event was bone dry. Even a week or so out, it called for cloudy skies, but no rain. Nada. My California blood, fingers and other extremities rejoiced. I don’t like mud, rain, wind or cold. Others embrace it but it’s not for me. I’m all for “softer times” these days. The previous year’s races instilled a fear of those three elements in my mind, hence my initial apprehension for agreeing to attend the Land Run 100 in 2018.

At some point, you have to put the fear aside, let it ferment for another, more pertinent situation and embrace challenges, no matter how large or small. My motivation to attend, document and race the Land Run 100 was dominated by the fact that this event is organized by a local bike shop. This shop, in itself, grew through its continued support of a community’s needs for bikes that are not just capable but excel at off-road dirt riding and racing.

Not having it be a muddy, cold and wet mess was the proverbial icing on the cake.


Kyle Kelly from Golden Saddle and myself boarded a plane at LAX with bikes in tow. After a few setbacks, we arrived in Tulsa and were picked up by Bobby himself in his Westfalia-converted Syncros VW van. Bobby is charismatic, to say the least. The man exudes an energy of the most positive light. He’s a beacon for the community, a rabble-rouser of positivity in a world increasingly cynical and bitter. He and his wife Crystal have created something wonderful in Stillwater. Kyle and I were anxious to experience it first hand. We all see these places on the internet, but what is it like in person?

Upon our arrival, we were whisked away to the Iron Monk Brewery, just a block from the shop, where entrants, spectators, and fans of the event had assembled for an early round of drinks, tales, and delicious food.

Friday was scheduled to be a relaxing day, with nothing on the agenda but our bike builds and equipment shakedown. I decided to do a pre-race spin, which turned out to be a hammer fest, no thanks to the other entrants who took this opportunity to shake off their anxieties. I wonder if people still thought in the back of their minds that it would rain? Or in some sadistic way, had hoped for it? Would this be their only crack at bone dry Oklahoma roads? We rolled back to the shop to find the street festival had begun and it was bumping. Our night faded out, through a total nüked sky and after getting dinner with friends, we headed home for a full night’s rest. I cannot confirm nor deny the existence of blood-red mud nightmares…

As a racer and a photographer, I had to think about the expanse of the Land Run 100, from start to finish. In anticipation for 1400+ entrants (actual numbers are still coming in, but at the last count prior to writing this, it was close to 1500) I decided to get to the shop early, drink coffee and go through my equipment, giving myself ample time to document the unfolding of this massive, police-escorted group rollout. We would have over 100 miles to log before the day would end.

Getting “the” shot, when you’re familiar with an event or course is easy; being thrown into the mix with limited knowledge presents a challenge, which in turn hones your skills as a photographer. In my experience, being in the front of the group is where the race’s moments unfold and dropping back throughout the day gives your documentation its well-rounded, final presentation. That was my plan and I was sticking to it.

With nervous legs, cold faces and jittery guts, the cannon fired and the race began. For the first 15 or so miles, I jockeyed for position at the front, staring down – or through rather – the dust stampede as seasoned roadies turned dirt road racers took off, trailblazing a clean path through the freshly-laid grey rock that, as a week prior, covered the fabled red dirt roads. It didn’t take long for this mad stampede to leave me and others in the dust. No hard feelings, it happens. Shot by shot, I dropped further back into the crowd, met new people, heard their stories, talked about their bikes, this website, and how no matter how “golden” it looks, it ain’t always sunny in California.

These stories are what make the event so magical. It’d be hard to record each verbatim, and honestly, that would exceed my abilities as a one-man show, packing a camera and racing a bike with so many dirt lunatics. Instead, I tend to keep those moments to myself and try to capture a fleeting moment with the release of my shutter button.

Smiling faces turned to pain as the rolling hills marched to their own beat of the drum. Throughout the afternoon, I would relish my snacks at the top of these hills, in between shots, and playfully heckle the racers as they crested the dirty hills, attempting to provoke a smile. “You’re making us look bad!” was yelled from time to time, followed by a smile and a thumbs up. The majority of people at the Land Run are in it for the experience, not for the podium. It’s these souls that have their own inner demons to conquer, their own goals to reach and exceed. Like Rob, who finished DK with seconds left on the clock, or the dude who rode in from Fayetteville, Arkansas wearing a short sweatshirt, resulting in the most hysterical sunburn, only to do the “Double” – a 50k run – the day prior. Bad. Ass.

With no water on the course and no support vehicles allowed, entrants were left to their own devices to survive. Or so I was told at the onset. Turns out, a lot of volunteers had set up water stations, an oasis filled with beer, good vibes, music, and smiling faces. Even the local Jeep club showed up on course, offering support for those with broken bikes or spirits. Speaking of spirits, I lost Kyle to a bar around high noon, when his bottom bracket began to give him issues. Kyle hung out at the bar for a few hours, scored a shirt, bought some racers drinks, and I’m sure gave the tender more money than she had seen all week. He still finished the race on his singlespeed Stinner with loose cranks.

For me, races like this would be easy enough to strictly ride, but photographing them creates mental and physical strain. My challenge is to always remember to put my body first and shoot when I see something about to unfold. I went through four water bottles, two sandwiches and a few pieces of candy I stuffed into my half frame bag. My banana must have jettisoned itself out of my pack on one of those rowdy descents…

Towards the end of the day, the city of Stillwater popped up on the horizon and I almost teared up. For no other reason than I knew my trip would soon come to close and I’d be leaving this place, the people, and the beautiful country roads. Dammit, Bobby, I’ll never be able to type that again without thinking about you screaming John Denver over a mic!

Upon rolling through the finish line, I received my Bobby Hug™, as well as a Tyler hug and smiles ad infinitum. Bobby went on to hug over 1000 racers, and he was out at the finish line until DFL crossed close to midnight. He’s a people person, with evangelical energy, and an infectious attitude of positivity. That man loves each and every member of his dirt-loving, cycling congregation. Those looking to find themselves, their souls and their inner strength on the endless dirt roads surrounding Stillwater, Oklahoma.

I’d like to wholeheartedly thank the entire team at District Bicycles, each and everyone who made it to the Land Run 100, you, for reading this piece, and viewing the photos. If you were on the fence about attending the event, I hope this swayed you and remember, it’s never too early to plan!

You can see my data at Strava.


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