Days 29–36: Firsts, Storms, and the Downhill Side of Halfway

Day 29 turned into the day of firsts.

We knew the heat was coming. Triple digits were in the forecast, and the Oklahoma winds were expected to start howling later in the day, so we made a strategic decision: get out early and push before Mother Nature started throwing punches. We rolled by 7:45 under overcast skies and manageable wind, and it proved to be the right call.

The first major milestone was crossing from Texas into Oklahoma. Almost immediately, the landscape changed. The dry plains of Texas gave way to fuller foliage and richer colors. The yellows seemed yellower, the greens greener. Funny how a state line can feel like someone adjusted the color settings on the country.

I pushed hard that day, maybe a little too hard. Forty miles disappeared quickly, and breakfast somehow turned into a late-morning McDonald’s stop before breakfast service ended. Along the way there were more firsts — a goat farm, my first escape from a dog chase, and eventually the first flat tire of the journey after more than 1,430 miles.

Ironically, the flat didn’t happen while I was riding. I was standing at a convenience store enjoying an icy when Scott pointed out bubbling sealant leaking from the gravel bike’s front tire. The cut was too large to seal. Then came the realization that, despite carrying spare road bike tubes and tires, we had neglected to bring extras for the gravel bike.

Preparation had met reality.

We hunted around Elk City for a solution — bike shops, Walmart, anything. No luck. Lesson learned.

Then Oklahoma reminded us who was boss. The wind came whipping down the plain. Hail hit the hotel windows before dawn. Gusts made riding dangerous. The weather forced another adaptation. Instead of fighting conditions that didn’t want to cooperate, we pivoted and headed toward Oklahoma City, where the Skirvin Hotel and its Peloton bikes became temporary headquarters.

Days 30 through 32 became a study in flexibility. I simulated two full ride days indoors, riding with Matt Wilpers, Christian Vande Velde, and Dennis Morton — Sayre to Weatherford, and Weatherford to Oklahoma City — logging more than 113 miles on the Peloton while the Oklahoma winds rattled the city outside.

I learned something important during those sessions. Peloton geometry works fine for workouts, but long-distance simulation is another story. The knees started talking back.

Oklahoma City surprised us in all the best ways. None of us had spent meaningful time there before. The downtown and Bricktown districts were clean, walkable, and welcoming. Public art was everywhere. The arboretum was well done. The Oklahoma City National Memorial was moving and impossible to walk through without reflection. We also came across “The Sit-In,” a powerful sculpture honoring peaceful protest and courage.

The Skirvin also had Boom Town Creamery nearby. As an ice cream aficionado, I was all in and indulged more than once. After grinding out miles indoors and navigating Oklahoma wind, a little ice cream and downtime felt like necessary fuel for the spirit.

Speaking of fueling, I shouldn’t leave out breakfast at Kitchen 324. You have to try their unique pancake, and Karen was a big fan of the apple fritter.

Amanda arrived and instantly changed the energy of the trip. She helped Karen and Scott with navigation, brought fresh enthusiasm, and reminded us how much fun family can add to an adventure like this.

Since we happened to be in town during the NBA Western Conference Finals, Amanda made the argument that sealed the deal: with Oklahoma City and San Antonio playing, we had to go. So we did. The winds outside were fierce enough to require walking at about a forty-five-degree angle to reach the arena, but once inside, the atmosphere was electric. Scott attended his first NBA game, the building was filled with Thunder blue, and we witnessed a double-overtime classic.

An unexpected bonus came at the Skirvin when I found myself sharing an elevator with broadcaster Mike Tirico. I handed him a No Kid Hungry Ride card and asked if he might pass it along to Reggie Miller, knowing Reggie’s passion for cycling and hoping maybe the ride might catch his attention.

The Oklahoma City stop also produced one of those unpredictable moments that seem to define this journey. A visit to The Oklahoman newspaper led to an interview and eventually a photographer meeting us outside the city for photos along Route 66. I’ll publish the link to the article when we get it.

Eventually the skies softened enough to get moving again. Amanda joined us for the ride into Stroud, where we passed the 20-foot-tall “You Are Here” push pin marking the halfway point on Route 66 between Chicago and Santa Monica.

Then it was on to Tulsa, with Amanda helping guide the team through another deceptively difficult day. What looked like a mellow 56 miles turned into a steady grind against false flats and persistent headwinds. The big news was reaching another important milestone: crossing the 1,700-mile mark.

Crossing the halfway mark carried real emotion. Somewhere north of 1,700 miles, the math finally shifts. I’m not naïve enough to think the second half is downhill, but psychologically something changes when you realize you’ve gone farther than what remains.

Weather, however, had other ideas.

The forecast showed four consecutive days of rain, which forced another adjustment and led us to T-Town Bicycles in Tulsa, where Nick helped us pick out a Wahoo KICKR trainer. That allowed us to ride the Cervélo indoors when conditions turned dangerous. That decision paid immediate dividends. Rain chased us toward Vinita, soaked me thoroughly, and eventually pushed us indoors, where the hotel room became training camp. Between outdoor miles and trainer miles, we kept the journey moving.

Then came another memorable encounter.

In the laundry room in Vinita, Karen met a young cyclist covered in mud. His name was Bailey McIntosh, a University of Pennsylvania student riding coast-to-coast in the opposite direction. We had breakfast together and traded stories.

Bailey had built his own bicycle and was riding solo with no support vehicle, carrying everything he needed. He was raising awareness for causes focused on expanding opportunity for others and simply grinding his way across America under his own power.

Watching Bailey was humbling. Here I am with Karen, Scott, Amanda when she can join us, the RV, logistics, navigation, and support. Bailey had none of that — just determination, a loaded bicycle, and belief in what he was doing.

Our paths crossed almost exactly halfway through our respective journeys, two riders moving in opposite directions, one twenty and one seventy-three. It reminded me not to take support for granted.

The ride into Joplin carried that reflection with me. Cornfields glowed in late light, wheat fields rolled toward the horizon, and the scenery reminded me once again how fortunate I am to see this country mile by mile.

From Pacific beaches to New Mexico rock formations, Texas plains, and now the green countryside of Oklahoma and Missouri, the Mother Road — as Route 66 is known — keeps changing and surprising us.

The weather still threatens. The miles still matter. But we’re past the point of no return now.

And that feels pretty good.

Please Help Us Fight Childhood Hunger

I am riding across the country to raise $1 million for No Kid Hungry, whose mission is to end childhood hunger in the United States. Millions of children in this country still face food insecurity, and that is unacceptable.

Every donation helps provide meals, support school and community food programs, and move us closer to a country where every child has enough to eat.

Please consider making a donation, sharing the ride with friends, or helping us spread the word.

Donate here https://p2p.onecause.com/markstrauss