Finding Magic at the Inaugural Mega Mid South

There was no worse place to talk to Bobby Wintle. Sitting in the middle of Stonecloud Brewery, a familiar haunt for both Stillwater residents and those who descend upon their small town once or twice a year, it felt like I could barely get a word in edgewise. He knew everyone. Everyone had something to say, and he had an impossibly equal, in-depth response to anyone who approached.

“Oh yeah? How’s the cousin? He’s playing today, right?”

“Yes, dude! This is RaShaun, he makes the best ice cream in town.”

“Heck yeah, man. Glad you finished.”

It went on like this for an hour. Intermittently interrupted by prodding questions about the industry, origin stories, and ideas about how to keep the impetus of The Mid South the same despite its ever-growing nature.

“People just kept asking me. You have to do an ultra. We want it. We need it.”

Astonished, I watched him lead a registration group ride earlier that day. Shortly after finishing Mega Mid South in just 47 hours and 30 minutes on a single speed, Bobby was back in the saddle, coercing people into their signature spring event. It didn’t compute. I couldn’t comprehend how this human being was moving around, let alone leading a ride, grabbing mics, kissing babies, and doing an interview. I was in Stillwater, Oklahoma, for the inaugural edition of Mega Mid South, a 300.9-mile bike race made largely of the perimeter of the last 13 editions of the The Mid South. The Mid South and its associated ultra rides and runs are hosted by Bobby Wintle, Crystal Wintle, and Josh McCullock, among a slew of other contributors, volunteers, and townsfolk. Leading into registration weekend for the smaller race in the spring, Mega Mid South checked off a variety of needs for the Stillwater-based team.

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“I didn’t want to take away from the festival that is The Mid South weekend in the spring, so, after a friend had gone out and ridden this massive route that encompassed a lot of past Mid Souths, he came to us and said, ‘Dude, you have to do this.’ But I’ve never hosted an ultra race. I didn’t know what it needed, and I wanted to do it right.”

“Were you nervous?” I asked.

“Fuck yeah!” Bobby said, laughing.

Lining up just outside District Bicycles in downtown Stillwater on Wednesday morning a few days earlier, there was an electric, albeit nervy energy. As Bobby corralled riders in front of the shop, thanking folks, noting stop changes, and tying up loose ends, it was clear a lot was happening. Not knowing how many of the 150 registered people would show up, Mega differed from the events Bobby and his team had become practiced at. Not only was this a free, largely self-supported venture, but temperatures were set to near 20 degrees above normal for that time of year. Instead of a balmy 75-85°F, temperatures for nearly all of its intended run time soared into the high 90s and even past 100. Well, at least it’s not going to rain, I thought.

Walking around the start line before the grand depart, I checked bikes and did my best to sus out whether people intended to ride or race. Upon direct inquiry, most people said, “Ride! I’m just trying to finish.” Whether it was a prior endeavor that had drained their fitness, a future commitment to do the same, or simply anxiety around the size of the task at hand, most people appeared focused on simply surviving. As riders made final checks and adjustments, the crew at District was hard at work ensuring everyone had what they needed in order to start. From brake bleeds to basic chain checks, they were set on getting anyone brave enough to line up to start the race.

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Without much fanfare besides some announcements and a leading charge from the man himself, we were off. Being my first bike event, I didn’t know what to expect. The “race,” if you want to call it that, seemed more like a procession for the first five or so miles. The long line of riders was so strung out that it was unclear where it started or ended or whether the “racing” had begun. As I settled into my own leap-froggy pace of chatting to other riders, stopping for photos and videos, and guilty pushing to catch back up, I thought about my preconceived notions for events in the bike space. I’d gravitated toward The Mid South for the same reason most do: it appeared atypical, even antithetical, to the flavor of events so widely advertised. A DFL celebration. Live music. The whole nine yards. Add in the fact that this relatively short-notice, ultra-adjacent version would likely be more experimental and low-key in its first year, and I was in. If I was ever going to do an event, it was this one.

While critiques and criticisms of the competitive gravel space are about as well-trodden as the roads that encompass them, I’d shied away from any sort of event for a variety of eccentricities—some particular to me and some not. While I’m something of a preferential loner who can don a charismatic mask, the thing that bothered me about the idea of event riding was the associated cost. Why would I pay anyone to tell me where to ride? I like looking at Google Maps for hours on end and figuring it out. I didn’t see the need for an aid station or any sort of expectation thrust upon me. I just like riding my bike! Why did it ever need to be anything more than that? As myopic and silly as that is to say, I like to imagine it’s a view that stems from a point of accessibility. Cycling is prohibitive enough. Why put an even greater barrier to entry? Soon, the juddering of my cockpit shook me from my innate cynicism, and I was staring at the tail end of 50 or so people. Back to reality.

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As the Oklahoma sun peeked from beyond an otherwise overcast and dramatically lit morning, the wheat separated from the chaff. Fully loaded bikes felt exactly as described, and the heat lit up the crushed gravel and clay roads. Sandpits and rollers aplenty, a gas station in Carney looked like a scene out of Saving Private Ryan. Harrowed, thousand-yard stares haunted the shady corners of what I can only describe as one of the most diverse and eclectic gas stations I’ve ever visited. From liquor to corndogs and something called a Cricket Lick-It—which, as you might imagine, is a real cricket encased in a hard candy shell—I witnessed people eat things that wouldn’t have made sense in the context of a comfortable day, let alone one where they intended to ride a bike in 95-degree heat. After about 45 minutes of recovering and hydrating in the shade, it was clear this was a race of attrition as much as anything else. With some new comrades in tow, we took off toward the first “official” campsite of the race near Lake Liberty at mile 100.

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Arriving at a scenic, sundown on the lake, a few riders were ahead of us enjoying food truck eats. Slowly but surely, riders poured into the gravel lot and shared tales of their long, hot century to that very spot. I felt increasingly bonded to the riders I’d stuck with, and we loosely formulated plans of attack for the next day or so over chicken teriyaki rice bowls and tacos. Eventually, Bobby rolled in like a bat out of hell. Last I’d seen him, he looked worse for wear as we prepared to leave Carney 40-some miles prior. He was anew. Entirely changed somehow but covered in the dirt and grime from the day’s ride.

“I feel so good right now. I’m riding this high. There were some real lows, but I feel so freaking good right now. How are you guys?!”

Something had possessed him, and as he sat and shared a meal with the ever-growing group of survivors, he announced he and a few others were going to ride through the night to Lake McMurtry, or perhaps further, to avoid the heat. Once again, I was baffled. The carrot on the stick throughout day one was the campsite, and I intended to use every moment of respite it provided to prepare for the next day. This multiple-business-owning father of two on a single speed was going to continue. What’s wrong with this guy? Looking to delay the setup of my opulent bivvy, I took to the lake. A fellow rider and I rinsed off and shared in appreciation for the water’s cooling effect on our sun-tinged flesh. A thorny campsite and a few moonlit conversations later, and we were off to whatever sleep we could manage.

Getting up in the morning was tough. Not just because of what we’d done to our bodies the day before, or because of the minefield of stickers (southern sand burs) that made it impossible to move more than an inch or two without getting pricked, or because we had to ride at least five or six miles of unknown terrain without any sort of food, or because the moon was so bright it robbed us of any quality sleep that night, but because of all those things at once. Endeavoring to be in the saddle by 6:30 in the morning, 6:45 came and went. Then 7:00. Then 7:30 before the slow parade of sad souls plodded away from Lake Liberty and toward Guthrie. Save for a sand pit or two, the Boomarang Diner in downtown Guthrie was the oasis amid an already tepid day. Horking—and that’s really the only way to describe it—a scrambler plate, we feasted on eggs, cheese, biscuits, gravy, and whatever accouterments sounded good. Washed down with a mix of hot coffee and ice-cold mugs of orange juice, we took an unnecessarily long breakfast. What awaited was some of the most significant “climbing” of the route and an ungodly heat that would rival that of my home state.

I add the scare quotes not because the elevation gain was anything to scoff at but because of the nature of Oklahoma’s rolling terrain. A Florida cyclist I may be, I’ve had the privilege to travel quite a bit this year. Colorado, Portland, Asheville, and other places I’ve been fortunate enough to ride through have thrown me into the deep end of what it really means to go up. The benefit in those places is one of stark dynamics. You climb for two, maybe even three hours, and descend in a fraction of the time. This course, though significant in elevation gain, was all rolling hills. Concentrated three-minute climbs at the most gave way to a roller coaster of constant punches that yielded varying levels of enjoyment. The baking sun of an unseasonably hot day made it semi-torturous. You could see the pain coming—sometimes for miles—as you crested a particular “peak” at any point in the day. There was nothing you could do about it. Just sit in and crank away.

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Eventually, our fractured group trickled into the Cowboy Travel Plaza around 1 p.m. I was lucky enough to escape the worst of the heat and found pretty much every rider, save for Bobby and his band of merry men, at said plaza. Irrespective of how fast or slow you progressed, most of the remaining riders met at this truck stop/gas station/barbecue joint. The heat was simply too brutal to push through. So, we waited. Among Gatorades, naps, fried pickles, and conversations about scratching, we waited. For hours on end, we watched the clouds roll across the vast plains as we recouped what little stamina we could muster. Talk of a storm system coming in worried many and put a set time on departing our beloved truck stop. Once more into the fray, the heat had barely dissipated. This was getting tough.

Arriving in the town of Perry, ominous clouds dotted the horizon. As I awaited the rest of the group to roll in, I hatched a persuasive plan. All my work in philosophical academia had to pay off, and it had to pay off right now. Poking and prodding for differing motivations, I asked the members of our world-class peloton to imagine a world. A world of air conditioning. A decent night’s sleep. An early morning pedaling to beat the heat after a legitimately restful sleep indoors. It didn’t take much, and as fate would have it, a six-guest Airbnb for a modest fee comfortably accommodating our weary crew popped up almost as soon as we searched for it. A dinner at a mom-and-pop shop later, and we were washing clothes, getting fresh, and wiping off two days’ worth of muck to great effect. It was the reset we needed to power us home.

Unbeknownst to us, Bobby had pushed on. Just as he said they would, his motley crew had ridden through the night and into the day until it was too hot to continue. Somewhere in Morrison, they’d laid down to “rest” in an alley behind a liquor store before trying to continue into the same night we crawled into our cozy Airbnb. The problem being the storms. They’d rocketed over the plains and sent a torrential downpour onto the group, who could do nothing but batten down the hatches. Stories of 70-mile-per-hour winds with water to match somehow made it onto social media, such that when we woke up, we were unsure as to whether the course was going to be rideable at all. Mud that shared more aesthetic commonality with primitive concrete than dirt coated their bikes. Watching on in horror, morale took a dive. But—I’m not sure if it was the video capturing Bobby’s sadistic laugh as he lay sodden in a bush or my desire to avoid going home knowing I had more left in the tank—I thought optimistically for once and said, “Let’s just see what happens, fellas.”

And we did. The dirt didn’t even get wet until 20 or so miles from Perry, and the little that did had seeped into the bone-dry soil. In addition to that bit of luck, clouds that dropped little more than a sprinkle loomed overhead, shielding us from the sun. It was the perfect six-hour window to put a massive shift in. We arrived in Pawnee at noon, bolstered by the progress and the fact that Stillwater was just 60 miles away. At the Sonic in the center of town, we ate and drank to our stomachs’ content. The attendant excitedly said, “You see that mud right there? That was from some folks that came in last night. Right before we closed.” Remnants of Bobby and company’s muddy trek stained the concrete, along with chili cheese dog sauce and Sonic Ocean Water. Along with the state of our dirty, sunburnt, dust-covered bodies, it was a sight to behold.

With one final push, we splintered. Different paces, aches, groans, and desires to finish at certain times gave way to a scattered attempt at covering an extraordinarily hot (have I mentioned the heat?) series of rollers between Pawnee and Stillwater. After what had to be one of the most beautiful golden hours I’d ever witnessed, most of my newfound friends and I rolled in together. The impossible task had become possible. It was no longer theoretical. There were no more ideas to hatch or plans to make. We crossed the finish line, and it was over. Our Mega Mid South was complete.

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As I sat at Empire Pizza guzzling NA beers and eating my weight in garlic knots, we shared stories of everything left untold. This would be a short novel if I detailed every significant moment of the 300.9-mile journey. Entire books could be filled with the observations, experiences, and self-discoveries that happened on this seemingly interminable set of dusty rollers out on the Oklahoma plains. But what I started to understand, as a cynic of all things good in this world, was the feeling I’d seen alluded to in The Mid South’s coverage. The reason to come back. The reason to care. Not only had I pedaled alongside these complete strangers, but I’d bled with them. Problem solved. Seen them in ways people who spend far more time around them might never see. That created a bond around a shared experience that was entirely organic. And that was special.

I rose early the next morning, excited to see what the folks at District had in store. As I rolled into town, I took stock of the cyclists preparing for various iterations of the registration ride. Just like I did a few days ago, they readied for a challenge, unsure of whether they’d finish. In addition to the commotion of the reg ride, the final Mega riders were still coming in. Each cheered in even louder than the last. Every rider was carefully captured by a motorcycle camera crew that’d been out on the course for days, covering riders at the back as clearly and with as much respect as those who had finished tens of hours or even days sooner.

“How do you keep this thing pure? How does it stay like this?” I asked Bobby at the crowded brewery a few hours later.

“We don’t have an axe to grind, man. We’re not here to say that we’re doing it better than anyone else or that we’re more grassroots or organic than any other race in the country. But we’re also not going to let anyone with a sack of cash dictate our future. The Mid South is not for sale—never will be,” Bobby said.

It was the question I’d thought about for months. Could this event really be so magical? Even if it was as holistically minded as presented, could the slow tide of performance gains and aero socks not turn it into all the other flavors of gravel on offer?

“We keep this thing like it is through intention. The intention of The Mid South has never changed. It has always been; we’re inviting our friends to do something they might not think they can do on roads we think they should see. That’s it. There is no ulterior motive or hidden agenda. The point is this! Is having this conversation with you, here in Stillwater, Oklahoma. You’re here!”

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I couldn’t help but be taken by the magic of it. I’d witnessed this guy look everyone in the eyes and meaningfully engage with them about a shared but deeply personal experience. Hug them and will whatever mysterious energy powers him into their bodies. It was a sight to behold and something that meaningfully affected not just the lives of those silly enough to ride their bikes across whatever distances The Mid South team had come up with but also those in the community. It wasn’t just bike people who interrupted our conversation. They were a mix of normal, everyday Oklahomans. People who had the financial realities of their lives fundamentally altered by someone who believed in sharing the beauty of a place long overlooked.

“People think places like this are full of dumb, uneducated, racist, bad people, but Stillwater is just like anywhere else. It has to be given the chance to be good, and The Mid South showcases the good in it and lets people put their best foot forward. I know it’s not like that, but I have to show other people and let them come experience that themselves so they can see what I see. So they can see the beauty of it.”

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As someone who has been quietly preaching the word of my home state for as long as I’ve been sharing experiences on the bike, that sentiment couldn’t have resonated with me more. It was true. People stick their noses up at the South. The best kinds of people with the best ideas and resources tend to leave. Talent is exported, and the beauty of a place hamstrung by its history is often never allowed to change. In the case of Oklahoma, I’d experienced it firsthand. I couldn’t understand how everyone was so nice. From gas station attendants in towns so small they could be biked across in under a minute to people slowing down on gravel roads so as not to knock the dust into your face, the kindness of the people here was shocking. No one wanted anything from you; they just wanted to know if you were okay.

Cynically, I wondered if it was all about the bikes. As I said, The Mid South has materially changed the lives of rural Oklahomans by the sheer nature of the fact that a bunch of affluent people who could afford to leave their lives to ride their bikes in remote places would come and buy up all their pickle juice and honey buns several times over. But, as I watched Bobby and the team at The Mid South authentically engage with anyone and everyone, I realized it didn’t really matter. For better or worse, money makes the world go round. That’s just the world we live in. The people preserving the sanctity of what’s being accomplished in Stillwater are doing so because they believe in what already exists there. The thing people turn their noses up at.

During a weary breakfast conversation in the dying days of the event, I sat with some of the locals who competed. The chat invariably meandered between our experiences and the nature of the terrain. As an oral history of mis-factoids went around, someone said Oklahoma had no national parks. That everything precious here was something worth drilling or mining or stripping from the land, so no one sought to protect it. Though it isn’t entirely true—Oklahoma has three national parks—the sentiment remained. We passed more oil derricks than I could count on our journey through Native lands. Speaking to a wide variety of people throughout the weekend, I learned of Oklahoma’s exploitative history and, as referenced, desire to strip this place of its “worth.” Intentionally or not, what the team at The Mid South appear to be doing is harnessing what can’t be bottled up, packaged, and sold. They’re spotlighting and putting on display what can’t be removed: the love inherent to the residents of Oklahoma. It’s what they’re powered by. It’s what drives someone to sit in city council meetings for years and speak to the economic impact of what bikes can do for a place like Stillwater and stick with it until that theory becomes a reality.

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The magic of The Mid South isn’t down to just one person. It’s a village of people believing in each other, themselves, and a place the rest of the country has all but forgotten. While the fields of Mid South’s past, current, and future are aesthetically defined by the oil derricks and mining roads that fueled the fires of industries past, the real source of definitive power left here is the one The Mid South is doing so well to preserve: love. Love was what defined the impetus of The Mid South, love was what kept people coming back, love was what got a group of Mega South finishers (including me) to go to a tattoo shop nearby on the final day and get the logo inked on our bodies forever. Heck, love was what created the routes that became Mid South as Bobby drove his nascent daughter along the roads that would define the course, just trying to get her to sleep. Love is what powers Mid South, and by god, it’s worth traveling a hundred, a thousand, or even a million miles to stand in the presence of.

Thank you, Bobby, Crystal, Josh, and everyone else who makes The Mid South possible. Thank you, Stillwater. See ya again in the spring!

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