The Future of Cycling is the Land Run 100, and I’ll tell you why

Reading Time: 7 minutes

By Andy Chasteen

The future of cycling in America has been a hotly contested topic over the past few years. How do we get more people riding bikes? Why is road racing in decline? Is dirt/gravel the future? What about the rising cost of cycling events? The questions rage on. And on. And on.

Rest easy, because I have come to answer those questions. I have the answers.

Events like the Land Run 100 are the future of cycling. They must be the future of cycling. It’s imperative that they are the future of cycling. I’ll tell you why…

COMMUNITY. That’s it. End of story. You’re welcome.

In a nutshell, that is the true and actual answer. But lets unpack it a bit…

For those who don’t know, the Land Run 100 is an annual 100-mile ride that was held this past weekend on the red dirt roads around Stillwater, Oklahoma. This year approximately 2000 spots sold out in less than 17 minutes, and in my opinion it’s the best cycling event in the United States. And here is why:

Land Run actually begins two days before Land Run begins. Thursday evening you roll into Stillwater and head straight to Iron Monk Brewery for the Beer Can Release Party. Reconnect with old friends and make new ones as you sip on special release LR100 Mid-South IPA. No cliques, no VIP area, no “what’s your FTP?” questions. If you love bikes of any kind, you’re in the club.

Oh, you ride bikes, but also love to run? The Double 50K Run begins at 8 am the next morning. This is for the real badasses – run the 50K on Friday, then do the 100-mile ride on Saturday. (I originally thought about doing this cause I desperately want to be a badass, but then promptly decided not to).

Soon after the badasses head out on their run, the LR100 Expo begins. Wander the blocked off streets around District Bicycles, Mid-South IPA in hand, and chat with good folks from Salsa, Zipp, Rapha, Skratch Labs, Industry Nine, Easton, SRAM, Kuat, Oakley, and Vittoria, just to name a few. Jump onto demos and games and bike art. At 1 pm, packet pick up begins and a no-drop group ride leaves that celebrates diversity, followed by a social hour a the local art gallery. 3 pm, another group ride of 300 humans rolls out of town where you can catch a rare bobcat-like siting of @ultraromance bringing up the rear of the ride, complete in his obligatory wool sweater and Bedrock Sandals.

The first Riders Meeting starts at 4 pm, and Bobby Wintle takes the stage to impart his nuclear energy upon all who attend. Rules, directions, tips, and more stoke than you could ever buy at Target. Or anywhere else for that matter.

Bands begin playing on the stage. Beer flows. People mingle and laugh – new friendships form and old ones strengthen. The talk forms around course conditions and where the mud pits are located. Tire choice? Did you drop a bag at the halfway point? Can you ride the mud or should it be walked? How many beers can your handlebar bag hold? Bobby jumps on stage at 6 pm and throws down a second riders meeting. The crowd is even bigger, the stoke even higher. The meeting ends and the crowd is slow to disperse, reluctant to leave this magical place of community and energy.

Saturday morning comes early, cold, and clear. Typical Oklahoma winds have calmed, and approximately 2000 beautiful people are gathering to embark on a mission. Everyone has their own goal – some want to win, some have a time in mind, some want to finish, and others just want to party.

Bobby rises to the stand and the crowd goes silent. He yells his familiar words of encouragement, but with new energy and conviction. The crowd goes nuts, it’s one minute to start. Bobby disappears to the side and grabs the pull cord to the cannon. He checks his phone, it turns over to 8 am, he pulls the cord and the deafening blast signals the start of LR100 2019.

Each person begins their own journey on these red dirt roads of rural northern Oklahoma. For some, it’ll be a rough day in the saddle. Many will race. Some will push towards their own personal goals. Others will ride all day with their friends, drinking a beer or two along the way. The course isn’t easy, littered with technical sections and a surprise or two that Bobby and his crew throw in to mix it up – mud, a water crossing, ruts, single track.

I wish I could tell you a thousand different stories of each person’s journey through this day. But I can’t. Only they can, and I guarantee they are all good. I saw their faces out on the course over the day. Emotions of pain, despair, joy, disappointment, elation. These stories could fill a book, a manifesto of sorts. We could call it A Guide to the Future of Cycling.


I’d tell you who won the race, but no one really cares (Sorry Payson, no offense. We still love you). Every person who came through that finishing truss won. Bobby’s tradition is to give every single person a hug who comes through that finish line. He hugged the first person through, and he stayed to hug the last person who came through in the dark, 11 hours later. You see, no one person at Land Run is more valuable or important than another. Everyone is in it together, from the pro who rolls in at the five-hour mark, to the casual rider who is fighting like hell just to finish on the same calendar day as he or she started.

Look me in the eye and tell me this isn’t special. Tell me this isn’t the future of our sport. Tell me a community like this isn’t sustainable.

The afternoon continues as thousands come in with that beautiful red dirt caked on faces, bodies, and bikes. And more hugs. The finish line block party goes on with food trucks and music and of course, more Mid-South IPA. As the sun dips low in the sky the awards ceremony begins. The irony lies at this moment as exhausted and weary riders (and runners) gather their remaining energy to celebrate all kinds of different achievements attained. The mood is electric. In true LR100 fashion, the best award of the weekend goes to the DFL Winner (dead fucking last).

Bobby didn’t start with Land Run 100. He and his crew started by building an amazing local community of dirt riders out of District Bicycles in that little college town of Stillwater. The idea was born from this community, and Land Run was built from the ground up. Grassroots. Community driven. Every person who has spilled their heart on that dirt owns a little piece of it. And that is the future of cycling.