07/09/2026
DAY 2 Ride — The Kevin Who Dropped Me
64 Miles, Alabama to Mississippi, and One Teenager With No Mercy
Day two started at 79 degrees.
After yesterday, that almost felt cool. My legs had not received that memo yet.
Today was 64 miles. My first full day of the tour. And if I’m telling the truth, my longest ride ever.
Now here’s the part where I confess something.
Before this trip, I had never ridden more than 20 miles in training. Not one time. So standing there in the parking lot looking at a 64-mile day felt a little like showing up to a spelling bee after only learning the alphabet.
But the bikes were ready. The kids were ready. So off we went.
The morning actually went pretty well. Good pace. Good legs. Everybody was riding loose, like the road had not started talking back yet.
We stopped for lunch somewhere along the Trace, refueled, and for a few minutes I thought, “Okay, maybe I’ve got this.”
Then we got back on the bikes.
Now let me tell you about Kevin.
Not me. The other Kevin.
Little Kevin.
Same name, completely different engine.
This young man played soccer before he ever got serious on a bike, and you can tell. He’s got those quick, strong legs that look like they were built for hills. Add in one summer of riding and a mountain bike season with us, and now the kid climbs like the hill owes him money.
I tucked in behind him for a while.
For folks who don’t ride, that means I was drafting. He was up front breaking the wind, and I was behind him trying to save every little bit of leg I had left.
I told myself I was fine.
I was not fine.
Somewhere on one of those rolling hills — and let me tell you, the Trace does not run out of hills, it just keeps handing you another one — Little Kevin came around me on the climb.
Didn’t look tired.
Didn’t look bothered.
Just looked back with that teenage grin and said something like, “You good, Kevin?”
Now when a kid you helped teach to shift gears a year ago says that while dropping you on a hill, it lands a certain kind of way. 😄
I can laugh about it now.
At the time, my legs were filing a formal complaint.
Not long after that, the cramps started talking. Nothing dramatic. Just that tight little warning that says, “We are no longer negotiating.”
So I backed off, found my own pace, and watched Little Kevin roll away like he had somewhere
important to be.
At one point, he was moving around 27 miles an hour.
I was moving at what I like to call “still technically riding.”
By the time I rolled into camp, I was done.
Not tired.
Done.
Kinney was there. Kevin was there looking like he had just finished a casual spin around the neighborhood. Joshua was there too, already settled in. He probably had been there long enough to start charging rent.
Nobody made a big deal about how long it took me.
They didn’t have to.
That’s the good kind of quiet. The kind that says, “We see you. You made it. You alright?”
And I was.
Mostly.
Somewhere along today’s stretch, we crossed from Alabama into Mississippi. The Natchez Trace Parkway runs 444 miles from end to end, and today we got to stand on that state line and take the picture.
For most people, it’s just a line on a map.
On a bike, after a day like that, it feels like you earned both sides of it.
Now let me tell you about camp.
There were two guys near us trying to put up a brand-new ten-person tent. They were looking at that thing like NASA had just dropped off a rocket ship and forgot the instructions.
We watched for about ten minutes before deciding that neighborly intervention was required.
We’ve got more than ten years of tent-pitching experience between us, so naturally we offered help. And by help, I mean we stood around giving a lot of advice about which pole went where and what might connect to what.
I’m not sure we made the process faster. But we did make it more entertaining.
Later, a group of motorcyclists rolled through celebrating the Fourth. Leather, tattoos, loud engines, the whole thing.
Turns out cyclists and motorcyclists have more in common than either group probably wants to admit.
Too much money spent on the hobby.
Too many weather complaints.
And stories that get better every time somebody tells them again.
That might be the whole tour right there.
Not just the miles.
It’s the people you didn’t know you were going to meet while standing next to a half-built tent, trying to act like you know what you’re doing.
And as for getting dropped by a young man I helped teach to ride?
I don’t know what else to do with that except celebrate.
That surge Little Kevin put in on the climb did not come from nowhere. That came from Sunday practices, reluctant hill repeats, mountain bike miles, and people who gave to this program without ever knowing whose legs they were building.
So if you supported Triangle Bikeworks, congratulations.
You helped build the kid who dropped me on a hill in Mississippi.
That’s not a bad problem for an old man to have. 🚴♂️😂
We’ve still got a lot of Mississippi left to ride. Every mile runs on gas, ice, food, water, and grown-ups willing to get out-ridden by the young people they love.
If this story did anything for you, put something behind it at trianglebikeworks.org and help us keep crossing state lines.