Last week, I embarked on one of my bucket list adventures: The Vintage 1000.
It’s a 5 day motorcycle endurance ride, organized by Speed Deluxe out of Chattanooga, TN. As the name implies, it’s meant to be archaic. The bikes have to be pre-1981, navigation is done with a roll chart, and everything you need gets packed on your bike - tools, spare parts, clothes, and camping gear.
A few months back, my friend David hit me up and asked if I wanted to do it with him and two of our other friends… I think everyone needs 1 solid gut check a year, and this was what I decided on... So, I said yes and quickly bought this crusty, non-running Honda XR500. I spent the better part of a year working on it. I’ve worked on bikes before, but I’d never done a trip quite like this. 1,000 miles of mostly dirt terrain through Colorado… with amazing friends… on a bike from 1979… seemed like a fun challenge.
Indeed, a gut check & challenge it was - not just for the 5 days we rode, but also including the months of prep, the travel to get there and back, and the mental toll of doing something new for the first time.
I took Friday off and started the 16 hour drive to Colorado - full of excitement, fear, and an eager grin to see some old friends. I packed the Landcruiser with just about everything I thought I might need - clothes, a collection of duffel and dry bags, tools, the bike, and too many spare parts.
I left Los Angeles around 12:30 - a terribly green mistake for someone who’s now lived here for 2 years. I sat in bumper-to-bumper traffic as I left the city limits and again on I-40 in the middle of the desert. The drive was more tiring than usual… it’s always nerve-racking when I’m towing something. My eyes tracked a constant loop - between the oil pressure, temperature gauge, and rearview mirror - for 520 miles. I spent much of Friday’s drive fueled by one of my favorite songs, Midnight Run by Charley Crockett (the namesake of my Substack). The odometer climbed as I listened to the lyrics:
“I’m taking me a midnight run.
A thousand miles or more I’ll drive, to where I lived when I thought I was alive.
They’ll never know I was ever around.
Just my shadow on the ground.
I turn east to face the sun,
After making me a midnight run”
So I pushed east late into the night, stopping in Arizona for a shower and a few brief hours of sleep. There’s something comforting about a hotel room - nothing is yours, unique, or particularly special… but you turn that TV to a random channel, crank the AC, and for 6 hours it feels otherwise. Enough to recharge me for the remaining leg through New Mexico and Southern Colorado, at least.
I woke up around 6, ate a despicable hotel breakfast that I was oddly thankful for, and got back on the road with a hot cup of coffee. I made it to Colorado Springs around 4:30pm on Saturday and unloaded the bike at one of my favorite places in the world: Boulder Street Moto. With the ride starting Monday morning, I had about a day and half to prep the bike and tie up any loose ends: re-jet the carburetor for altitude, swap the front wheel, and double check everything that could fall off or fail in the next 1,000 miles.
Other riders were already working on their bikes by the time I got there, which immediately made me feel like I was behind the 8 ball and sent me into a brief panic. “Chop wood, carry water” I told myself.
I chipped away at my prep list, feeling more secure with every little bit that got checked off. My friends stopped by the garage to catch up and hangout - a really welcome sight. The best kind of friends are the ones that can pick up from wherever you left off - even if that was over a year ago. We sat around the bikes, focused more on talking shop/life than we were on turning wrenches, until about 2:30am.


Sunday was more of the same - prepping bikes, trying to relax my mind, and making sure I didn’t forget to pack anything. My mind was moving a million miles an hour. I’d done all the prep I could think of, which calmed me slightly, but the nervousness and apprehension I had about the next five days didn’t truly subside… a feeling that brought me back to my sports career.
Even as a college player, I got nervous before games. Just like the process of building this bike, I did all the prep work… paid attention in practice, watched film, read the scouting reports. I remember my dad asked me about it one time, and I said “yeah, I always get nervous beforehand. It goes away when I start playing, though”.
I wasn’t ever able to shake those pre-game jitters, and I certainly wasn’t able to shake them ahead of the Vintage 1000 either. Sunday night, I stared at the ceiling for a good hour until my mind was quiet enough to fall asleep.
My eyes opened on Monday morning to a 5am alarm. Day 0 was over.
Time to saddle up.
To be continued… thanks for reading.
bad ass, hope you find some time to fish!
The one gut check a year mentality is the best mentality.