The Riders We Never Forget: How Chance Encounters Leave a Lasting Mark
There are two rides that stand out in my memory, even though years — even decades — have gone by. I never exchanged full names or kept in touch with either of these people. But they’ve stayed with me, clear as a tailwind on a sunny day.
100 Miles of Camaraderie
One year during the 24 Hours in the Canyon event at Palo Duro Canyon, I found myself riding the first stretch alongside a man I had never met before. We were similar in ability and resolve, and it just worked. We climbed out of the canyon together and covered the first 100 miles side by side, talking like old friends the entire way.
I don’t remember his name now. I think he was from somewhere near Amarillo. But I do remember how much we had in common — our mindset, our pace, even our attitude toward the challenge ahead. We shared stories, tips, and a sense of purpose. It was the kind of connection that feels rare but natural, the kind you don’t have to force.
Once we returned to the canyon and started riding the 5-mile loops that continue through the night, we drifted apart. I never saw him again. But I still think about that ride. About how much I learned from him. About how that kind of chance meeting can become one of the highlights of a long event — maybe even the part you remember most.
A Ride Through Arlington — and a Memory That Lingers
Even farther back — all the way in the 1980s — I was on a family vacation to Arlington, Texas, visiting Six Flags. I’d brought my bike along and decided to sneak in a ride one morning, heading south of town onto what were then quiet farm roads dotted with new developments and shopping centers.
Out there, I caught up with a woman riding the same model bike as me, just a different color. We started talking — first about the bikes, then about everything else. We discovered we were both teachers, close in age, and had an incredible amount in common.
We ended up riding 40 miles together, completely lost in conversation. When we returned, she invited me to her house to clean up after the ride. I declined — I was married, and she was single — and I felt it wasn’t right. But I’ve thought about her often over the years. She was gorgeous, smart, and fascinating. It’s hard not to wonder what would’ve happened if we’d met at a different time. Or if I’d at least exchanged contact information. Would we still ride together now and then? Would we still talk?
I’ll never know.
A Chance Meeting from the Other Side of the World
More than forty years after that ride through Arlington, cycling reminded me again how small the world can feel.
During my Mississippi River Trail ride this year, I caught up to a couple from Perth, Australia. They were traveling in the same direction I was, but unlike me, they were carrying everything they needed for months on the road. Their bicycles were loaded with panniers and camping gear, while I was riding a vehicle-supported tour with only the essentials.
They had flown to Washington, D.C., and were making an incredible journey across America. They had briefly followed the Mississippi River Trail before turning west toward Omaha, Nebraska. From there, they planned to continue all the way to Washington State before eventually riding back to Missouri to visit friends before returning home to Australia.
As we talked, I mentioned that I was from Lubbock, Texas.
His face lit up.
"Lubbock is the real Texas," he said with a smile.
Ten years earlier, he had ridden his bicycle across the United States from the West Coast to the East Coast, passing through Lubbock and the Texas Panhandle along the way. When we compared notes, we realized something remarkable. That same year, I had ridden from Lubbock to Pensacola, Florida. Our tours had taken us along many of the same roads, separated by only a couple of months.
We may have passed through the very same towns, stopped at the same convenience stores, or even eaten at the same cafés—never knowing another touring cyclist was following the same route just weeks later.
The cycling world suddenly felt very small.
We talked for about twenty minutes, swapping stories about the people we'd met, the places we'd seen, and the adventures that only traveling by bicycle can create. I could have listened all afternoon.
Eventually it was time to continue. I wished them safe travels, climbed back onto my bike, and rode ahead while they settled back into the steady rhythm of their fully loaded touring bicycles.
I'll probably never see them again.
But for twenty minutes on a quiet stretch of the Mississippi River Trail, three cyclists from opposite sides of the world discovered that our paths had nearly crossed a decade earlier—and that a shared love of bicycles can make a very big world feel surprisingly small.
Why It Matters
What I do know is this: some people enter our lives for a short stretch of road, and then they’re gone — but they leave something behind. A sense of connection. A reminder of what matters. A memory that lasts longer than you’d ever expect.
Cycling has given me a lot over the years — health, freedom, and purpose. But it’s also given me moments like these. Unexpected, powerful connections that unfold under the open sky, with the road stretching ahead and no destination in mind except forward.
So if you ever find yourself riding next to someone and the miles start flying by a little faster — pay attention. You may be sharing something that lasts far beyond the ride.
It wouldn't be an Old Guy Bicycle Blog post if I didn't leave you with one last tip. After more than 50 years in the saddle and over 155,000 miles of riding, I've learned what works—and what doesn't—for an average cyclist like me. Every item on my Cycling Gear I Actually Use page is something I personally ride with and trust. I tend to be pretty frugal, so you won't find many expensive, top-of-the-line gadgets. Just reliable gear that has earned a place on my bike ride after ride. If you're curious, take a look—you might find something that makes your own rides a little better.
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