Day two was Century Day: 106 miles from Chesapeake to Richmond.
We began by riding over to the hotel where we had gathered the night before. Everyone formed up for another group rollout, but before we left, I had the chance to talk with former Chief Master Sergeant of the Air Force James Roy.
Chief Roy was the CMSAF when I first joined the Air Force, so meeting him already felt significant to me. At one point, he needed to walk away and asked me to hold his bike for a second. I know that probably does not sound like a big deal, and objectively, it really was not, but I thought it was the coolest thing ever. Sixteen years ago, he was the highest-ranking enlisted Airman in the Air Force as I was beginning my career. Now we were standing together getting ready to ride a century.
After another police-escorted rollout, we settled into the day. The first half took us toward Jamestown, where we loaded our bikes onto the ferry and crossed the James River. It was one of those experiences that broke up the ride perfectly. For a little while, we were off the road, standing on the ferry with our bikes and watching the water instead of the wheel in front of us.
After crossing, we stopped for lunch at a brewery just off the trail. A ferry ride and a brewery during a century ride is a pretty solid way to spend a Friday.
From there, much of the remaining route followed the Virginia Capital Trail toward Richmond. The trail was beautiful. quiet, mostly protected from traffic and surrounded by trees for long stretches. After the heat, traffic and open roads of the first day, it was some of the best riding of the entire trip.
Surprisingly, most of Century Day felt easier than the 96 miles we rode on Day 1. My body had started to understand what we were doing, and for much of the day I felt strong.
Then I reached approximately mile 80.
I was riding alone, struggling and moving at around 14 mph. After nearly 180 miles in two days, my legs were beginning to feel every one of them. Then a group of cyclists came past me in a pace line.
“Grab a wheel.”
That was all I needed to hear.
I jumped onto the back, and almost immediately we were moving at around 20 mph. The effort did not disappear, but everything changed once I was no longer fighting the wind alone. I stayed with them all the way to the final rest stop, and that pull gave me exactly the boost I needed to finish the day strong.
That moment captured what M2M is really about. You may be capable of covering the miles alone, but that does not mean you always have to. Sometimes you are the person doing the pulling. Sometimes you are the one struggling. And sometimes a group comes alongside you at exactly the right moment and simply says, “Grab a wheel.”
We finished in downtown Richmond with 106 miles completed and 202 miles covered in two days. After getting cleaned up and settling into the hotel, I still had one final mission: finding breakfast for the next morning. With another early rollout coming and limited food options nearby, I ordered groceries from Kroger through Uber Eats and made sure I had what I needed.
It was not exactly an exciting night in downtown Richmond, but food, a shower and a bed were all I wanted by that point.
Century Day gave me a ferry ride, miles of beautiful trail, a memorable moment with Chief Roy and one perfectly timed pace line. More importantly, it reminded me that the real strength of this ride comes from the people sharing the road.
Day two complete. Halfway to the Air Force Memorial.