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GRILLING. BBQ. CAST IRON. RUNNING. BIKING. DOGS (THE GIRLS)

Mid South 2025

The Mid South gravel race in Stillwater, Oklahoma, has been on my bucket list. I’ve watched countless YouTube recaps in awe, captivated by the challenge of riding over 100 miles of red dirt gravel with enough elevation to make this Central Illinoisan pause for a deep breath.

I signed up for the 100-mile race back in September, understanding that I have to keep my fitness up throughout the winter, ride some cold outside miles, and long in-door miles. The training wasn’t ideal with work, life, and weather, but I squeezed in some long-distance rides a couple of weeks before the event to be ready enough. 

My coach, aka my wife, told me not to come back home unless I crossed the finish line except for blood or mechanical. 

I made the eight-hour voyage to Stillwater, Oklahoma, with my riding buddy, Michael Phelon. He was the reason I was going. I had mentioned the bucket list race once on a ride, and he held me to it. He called me the day registration opened and said, “Let’s go!”

We made it to Stillwater on Thursday in time for the denim ride. It’s a party-pace ride where you wear your best denim, whether a sleeveless jean jacket, jorts, or a Canadian tuxedo. Michael and I thought we could stroll into a Goodwill before the ride and find something. Little did I know that denim is a hot commodity, and there wasn’t much of anything.

As we headed out on the denim ride, Bobby appeared out of nowhere like Willy Wonka, making a grand entrance. He began riding alongside Michael, who engaged Bobby in conversation, and they took a mid-ride selfie. Bobby sported cowboy boots and a denim vest.

While cruising through a disc golf course, I noticed Ben Delaney, a prominent cycling YouTuber, getting some B footage. We rode out 6 miles to the crest of a hill in the middle of the country with views of cattle ranches, cedar trees, and blue skies as far as you could see.

Ben Delaney was walking through the crowd, and I pointed him out to Michael. Michael, never one to miss an opportunity to make a new friend, said hi to Ben and started chatting. The next thing I knew, we were getting a picture together. Ben then asked if he could interview us about Mid South and our bikes. 

‘The Lollapalooza of Gravel’: What brings riders (back) to The Mid South

We were both interviewed, but I got picked up for 15 seconds of fame with my quote about the “Lollapalooza of Gravel.”

Friday morning was the start of the ½ marathon and 50K running race. Some runners were doing the ‘double’ in which they ran the 50k and would ride the 100-mile gravel route the next day. 

Later that morning, the expo started. Something about a race expo just puts me in the mood to spend some cash. I bought a stainless steel water bottle, signed up for several newsletters to get free stuff, and bought an American-made top tube bag – it makes my bike look faster. We ate some Ted King ice cream, got interviewed on Jerimiah Bishop’s IG live, and walked right by Pete Steitina.

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A post shared by Jeremiah Bishop (@jeremiahbishoprides)

Michael has great instincts for putting us in the right place at the right time, and we somehow found ourselves in front of the check-in line. I was able to score a coveted low race number 3. The race schwag bag included a paint stick for scraping off mud, a bluff, a key chain, and a custom Topo zipper bag.

It had been windy that Friday morning, but the wind was starting to pick up. The expo tents started moving and coming apart. We also smelled fire; smoke was beginning to enter the air. Shortly after, we saw a message that the expo and registration were shut down until the afternoon. The wind had picked up so much that porta-potties were turned over. We headed back to the hotel to wait out the wind.

We speculated about whether the race would happen. We watched the news and saw reports of multiple fires around Stillwater and the state of Oklahoma. We met up with a fellow SBC member and my neighbor, Steve Schroll, for some Mexican food while determining our next move. 

The skies were dark and it was starting to smell like a charcoal pit, and the air quality was horrible. The day after, I felt like I had smoked a pack of cigarettes. I constantly refreshed Instagram to see if the race had been canceled. Around 8 p.m., a video message was posted saying, “The race is on until it’s not.”

There were reports on social media that some were being evacuated south of our hotel. Begrudgingly, thinking that the race was unlikely, we went to Walmart and stocked up on water and other essentials to be prepared to ride the next day. 

The next morning an announcement had been made that the race was canceled even with the Simpson colored blue skis. There was still a lingering smell of smoke and ash on the car windows. Later on we found out that 70+ homes had been burned down in the fires. It put everything in perspective and us not being able to do a bike race was the least of our worries.

The three of us discussed alternate plans and looked to do some kind of ride. Mid South posted a 50-mile that would take us away from where the fires had happened. We met in downtown Stillwater and headed east. As we exited the town, the landscape turned to cattle ranches with rolling terrain. Cedar trees lined the road. With dry grass and cedar trees and gusts of 60 mph winds, you could understand why the fires consumed so much the day before.

With over 2800’ of climbing, it wasn’t the most leisurely ride. The 100-mile ride we were supposed to do was 6500’ and 107 miles. The gravel roads we were riding on our alternate route were very similar to Central Illinois, unlike the red clay dirt ones I had seen pictures of on social media. There were a handful of other riders doing the ride as well. We talked with riders from Los Angeles, Austin, Minneapolis, and the east coast. Since it wasn’t a race, we stopped and had multiple photo moments. A headwind on the way back into town made us grateful that we didn’t have to tackle it for another 50 miles.

Mid South would also feature two days of music on Friday and Saturday. It was cut short by the wind, but some bands still played on Saturday. Before the event, Mid South had assembled a Spotify playlist of all the bands playing. One artist that stuck out was Zach Person. He sounded like a cross between Hendrick, the Black Keys, and Prince. I was in the front row with the biggest smile. I am convinced everyone else will know about him in the next year or two.

In between songs, Meg Fisher, a Paralympic champion cyclist, came to the stage to announce that she wanted everyone to go out in front of the bar to welcome Jacob Keen finishing his 80 mile bike. This was going to be Jacob’s longest ride since losing his lower leg after being struck by a vehicle while riding his bike. He was under the impression that he was finishing in the dark with limited fanfare. Everyone went outside, turned on their cell phone lights and we waited for Jacob’s headlight. The crowd was chanting Jacob’s name as a dim light appeared at the end of the street. Everyone erupted as he rolled up to the front of the bar. Meg Fisher and race director Bobby Wintle welcomed with a big hug. Jacob removed his prosthetic and lifted it in the air. It was a scene from a movie. It was a really touching moment that I got to see first hand.  

Even though the 100-mile race was canceled, the Mid South experience was far from a disappointment. The camaraderie, the unexpected encounters with cycling personalities, the shared adventure with friends, and the powerful moment of celebrating Jacob Keen’s achievement made the trip memorable. While the fires and cancellation were disheartening, the alternate ride and the musical discoveries provided unexpected joys. Ultimately, the true spirit of Mid South, the sense of community and resilience, shone through despite the challenges.


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