You might be wondering, out of all the gravel events popping up around the world, what makes the Land Run 100 special? Why ride gravel in Oklahoma, in a place known as “Tornado Alley”? If you are wondering this, you are not alone.
Last week, I had the opportunity to participate in my first Land Run 100 gravel race. Bobby and Crystal Wintle host the event from their shop, District Bicycles, in the center of historic downtown Stillwater, Oklahoma. The race attracts two thousand gravel cyclists from around the country and has some legendary stories attached to it. For instance, in 2017 rain soaked the red dirt roads to the consistency of peanut butter mud and only ~25% of the riders who started the race finished. Despite the treacherous conditions that bad weather can bring on race day, the Land Run 100 has established itself as a must-do event on the gravel race circuit. Before I talk about why I think that is and what I learned from my experience there, I’d like to acknowledge the history behind the name of the event.
The name Land Run refers to a historical event in which previously restricted Native American lands were opened to homestead on a first-arrival basis. The most famous land run was the Land Rush of April 22, 1889 where 50,000 people lined up on horseback, wagon, and foot to be the first to claim their parcel of the two-million acres available of what is now the state of Oklahoma.
After years of raids and political pressure by the Boomer Movement to acquire these restricted, yet desired native lands, the U.S. Government appropriated the land from Chickasaw, Choctaw, Cherokee, Creek, Cheyenne, Comanche, and Apache tribes through the Indian Appropriations Act of 1889. Many of these tribes were originally displaced to this region by the Indian Removal Act of 1830 along the Trail of Tears. These native lands were ultimately made available to the public and for a series of land runs through the Homestead Act.
An article in the New York Times, Into Oklahoma At Last, describes the scene from the day of the first official Land Run on April 22, 1889 in what is now Stillwater, Oklahoma.
“A great change has come over this town. Yesterday it was a metropolis, to-night it is a hamlet in point of population. The metamorphosis was effected at 12 o’clock to-day, when several thousand men, women, and children crossed the Canadian River and entered upon a wild struggle for homes in the promised land… In they go, helter-skelter, every rider intent on reaching the bank first. There goes a horse into a deep hole and his rider falls headlong out of the saddle.”
The scene of the first official Land Run of 1889 was not so unlike the scene of the morning of the Land Run 100 gravel race of 2019. However, we were there for a radically different purpose. Rather than white-settlers stampeding their way to lay claim on native lands, gravel racers from around the country were lining up at the start line, chomping at the bit to claim, not land, but the glory of the ultra-endurance feat of riding 100-miles of Oklahoma’s historic and notorious red dirt.
Obviously, the inspiration behind naming such an event pays homage to the anglo-history of the chaos of how the town of Stillwater and the state of Oklahoma came to be settled. It’s very similar to the spectacle of 2,000 gravel racers ascending on a town for a long-weekend. The reality is that the name behind this race has some historical baggage that begs the question, “should we be celebrating it?”. If the answer is yes, I believe it should be done in a way that promotes a greater awareness among participants of the whole history behind the name. It’s a challenging, controversial, and daunting task but it can be accomplished with the help of a community. After all, realizing our potential to overcome challenges so we can be better in the future is why the Land Run 100 gravel race was created in the first place.
What I came to realize over the 4 days I spent roaming around Stillwater was that what makes this event so appealing over other gravel events is the community that comes together to generously give their time, energy, and space to make 2,000 strangers feel like they are part of the family and returning home after a long journey. You all know by now about the infamous loving energy of the race promoter, Bobby Wintle, who hugs each individual rider that crosses the finish line. But do you know about Keith, Barb and the countless others who host cyclists in their homes? What about Crystal? Who organized scholarship opportunities for WTF cyclists to participate in the race and a WTF ride party to celebrate all 200 WTF cyclists registered for the event? What about Sally and the countless volunteers who made sure everything happened without a glitch? The collective effort, energy, and love shared by the people of Stillwater was enchanting and is obviously what will keep people returning home for years to come.
I am no stranger to these events; I entered the gravel race scene back in 2013 with races such as D2R2, Three Peaks Ultra Cross, Gravel Grovel, Rouge Roubaix, Almanzo 100, Barry-Roubaix, and Ride Ten Thousand. To give you some context of where I was as a cyclist in those days, I usually finished so late that there was no more free food left at the finish line. Alas, I didn’t think I was cut out for this sort of thing. I hated pain and I enjoyed taking pictures and breaks too much to justify the expense of race entries. So I started breaking away from these events to do my own thing, exploring via bikepacking full-time. I briefly returned to the gravel racing in 2017 for the Dirty Kanza 200 which was enough of an experience for me to relapse into bikepacking full-time again.
With bikepacking it can sometimes take an entire day to travel 25-35 miles. During many trips I often ask myself, “Am I even capable of riding 100-miles anymore? What has happened to me? All I do is eat, sleep, smoke weed, and ride slow.” So, after I signed up to do the Land Run 100, I set a goal for myself to use the challenge to gauge my fitness and to go as fast as I could, for once in a long while.
On the Friday before the race, I was wandering around town as Bobby was hosting one of the pre-race meetings. Over the sea of gravel punks, spandex kits, and ultra pros I heard Bobby say that we could all learn how to deal with pain better. It is a transformative skill that can be practiced during these ultra-endurance events that we can carry into life’s many real challenges. This stuck with me during my Land Run 100 gravel race from the moment the start cannon fired, through hugs at the finish line, to this very moment, as I write this story.
I am so privileged when it comes to gravel riding. You could call me a gravel snob. As a professional adventure cyclist, I spend most of my time seeking out the best gravel roads through the best scenery I can reach on two wheels. I have also ridden across the great state of Oklahoma on dirt roads before, so I mean this with no offense that I was personally not at the Land Run 100 for the scenery. I was there to see how fast I could get it done and to socialize before and after.
My strategy to get it done as fast as possible was to line up in front with the fast folks, hang on for dear life, and keep stops to a minimum. I don’t do intensity often, so the first 55 miles of riding with a group too fast for me was pure agony. I have no idea how people can talk in groups like that. My apologies to anyone who tried to talk to me and I only responded with “grunt.” My legs were frozen stiff, my all carbon bike felt like it weighed 100 lbs, and I had a wicked stomach cramp for a solid chunk of time. At the one and only checkpoint, I finally lost track of my group. My spirits were low, my negative self-talk was high, and my belly very empty because after all this time I still struggle with eating while riding. I slugged a Coke, filled my bottles, and immediately hopped back on my bike and onto the course.
Free from the crowded pace line I could absorb my surroundings, ride my own line, snack, and eventually find my mojo. I had surpassed the pain and transcended into a calmer space where I was more present with myself, my needs, the color of the red dirt, the blue sky and the grey trees– a countryside on the verge of Spring. Before I knew it, I was having a blast! At least for a solid 25-miles until the pain crept back, tapping me on the shoulder and letting me know it was time to take care of myself again. Bobby’s words would come to mind, that the pain is only temporary. I ate, drank, stretched and transcended again.
I had forgotten to look at my ride time all day since I was fixated on how many miles were left. So, after I crossed the finish line, received my hug, and an ice cold La Croix, I was surprised to see I had completed the ride in 6 hours and 28 minutes, securing 14th Woman Overall and 3rd place in the Women’s 30-39 category.
Something about the gravel race environment finally clicked for me at the Land Run 100 and I think I’m finally hooked. What I learned is that success is not indicated by a time or a place. It’s the experience of surpassing the pain and discomfort of an extreme challenge and entering into a euphoric state and getting to say, “I had fun out there despite how painful it was.” The ebb and flow between pain and euphoria is like an addictive rewarding drug. No wonder people keep coming back for more. Thank you Bobby, Crystal, Sally, and Stillwater.