Bossman Rides
Two wheels. One mission. Founded by Army veteran Jeremy “Bossman” Caudill we ride for the 22 and 1 — road grit, brotherhood, and freedom on every mile. 🇺🇸
Where road grit meets American backbone. Army veteran Jeremy “Bossman” Caudill leads the ride — honoring the 22 and 1, standing for freedom, and living wide open on two wheels. Every ride we film, every mile we share, shines a light on the battles veterans still face and the brotherhood that keeps us rolling. This isn’t just a page — it’s a movement of riders, vets, and freedom-lovers who believe in living loud, giving back, and never leaving a brother behind. Along for the ride is the Favorite Redhead — passenger, storyteller, and editor-in-chief with a strong cup of coffee in hand. The mission is the fuel, the open road is the altar, and together we ride for the 22 and 1. 🇺🇸
#RideForThe22 #VeteranStrong #BossmanRides
09/27/2026
Some of the best stories from the road start with a tattoo.
I get more questions and comments about the one on my back than just about anything else, so I figured it was time to share the story behind it. Twenty years ago, I met my good friend bodean and his beautiful wife, Penny, at the Easy Rider Bike Show at the Veterans Memorial Center in Columbus, Ohio. Bodean gave me this awesome tattoo, and what started as a chance meeting turned into a friendship that’s lasted ever since.
Now Bodean and Penny have invited my favorite red head and I to stay in their cabin at Cumberland Lake near Cumberland Gap. How cool is that? It’s a reminder that the best part of riding isn’t just the miles or the places you see, it’s the people you meet and the friendships that stay with you long after the ride is over.
To Bodean and Penny: thank you for the friendship, the memories, and the generous invitation. I can’t wait to make another memor.
And to the whole Boss Man Rides family: every ride has a story, and sometimes a friend’s kindness becomes one of the best parts of the journey. If you’ve got a favorite road, a good story, or a little hospitality to share along the way, reach out. You never know where a conversation, or a friendship, might take us.
09/27/2026
A lot of you may not know that my favorite Redhead grew up on a huge pig farm with her two sisters. They were out there doing all the hard work, and if this picture tells you anything, it’s that when something needs doing, she’s right on it.
She still brings that same determination to every ride. She takes the best care of me on the road and is always ready to do whatever needs to be done. I’m one lucky guy to have her riding by my side.
Give a little love to my favorite Redhead!
09/27/2026
This fog is so thick, you can almost feel the water in the air! Perfect kind of day to slow down, take it all in, and give a big shout-out to the businesses that support Boss Man Rides and all the adventures we take.
A huge thank you to Robmylender.com and Triple R Auto Glass for being part of the Boss Man Rides family and supporting what we do. We truly appreciate you!
If you’ve got a chipped or cracked windshield, give Triple R Autoglass LLC a call. And if you need help with a mortgage, reach out to Robmylender.com. Please support the businesses that support our rides!
09/26/2026
Sometimes we have to turn around for a picture!
09/25/2026
No telling what we are going to see!
09/25/2026
We’re officially underway! We were planning to have dinner at the Manchester Tavern, and then we both realized we’d never taken Route 93—Manchester Road, all the way down to Kentucky.
So that’s the plan now: we’re taking the road less traveled and seeing where it leads. See you guys in Kentucky! 🤘
And we’re off. 🏍️
Bossman and the Favorite Redhead are pulling out of the Bossman Rides HQ and pointing the bike toward Myrtle Beach.
We’ve got some miles to ride, some back roads to find, and apparently a little business to handle along the way. 😂
One of our side missions on this trip: scouting places where Bob's Hamburg on Wheels truck could set up for the winter.
So if you know a good spot along our route — Nashville, the Carolinas, Myrtle Beach or somewhere we haven’t thought of yet — tell us where we need to look. 👇
Let’s see where this ride takes us.
🇺🇸 We ride for the 22 and 1.
09/25/2026
My good friend Micah took this pic here at Bossman Rides HQ. Lots of wildlife
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Myrtle Beach, SC
29572, 29575, 29577, 29578, 29579, 29586, 29587, 29588