Bossman Rides
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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
08/05/2026
This one's personal. 🏍️❤️
KimTam Park isn't just a swimming lake to us. It's Bossman Rides Headquarters.
It's where thousands of bikers have gathered, friendships have been made, veterans have been honored, and memories have been created.
Today, we received our official 2026 Bathing Beach Water Quality Summary from the Summit County Health Department, and every single water sample tested this season was acceptable for swimming.
To some, it's just a report.
To us, it's proof that we're taking care of a place that's become home to so many in the riding community.
Whether you've stopped in for a Bike Night, a burger, a benefit ride, or just to cool off after a long day in the saddle, thank you for making KimTam part of your journey.
We're proud to call this place home, and we're committed to keeping it clean, safe, and ready for the next rider who rolls through the gate.
We'll see you at HQ. Ride safe, and keep the shiny side up. 🏍️💙
We just rolled up near the very top and I swear this spot looks like a straight drop off. Like… you can almost hear your bike go “yep… I’m doing this.”
Now I need the group to answer—be honest:
Would you ride up here if the view looked like a cliff wall straight down?
How steep is “too steep” for you—like what’s your limit?
Are you the “send it” type… or the “I’ll admire from a distance” type?
What would you do first: grab a selfie, take a deep breath, or pretend you’re not nervous? 😄
Drop your answer in the comments and tell me your confidence level from 1 to 10.
Riding Trail Ridge Road! Bossman put his hoodie. 57 degrees is a big change compared to 96! See you all in Sturgis will soon!
08/04/2026
8:28 Bossman: " Think we can get packed and to the Rockies by 9?"
5 seconds later Favorite Redhead "sure!"
8:51 we pull up to the entrance
08/03/2026
Do you ever meet someone and just know your hearts and souls are connected? Since hitting 40 these are the women I live to meet! When you feel it in your bones your just meant to be friends. When one goodbye hug isn't enough and you both end up with tears in your eyes over a chance meeting!
Red Rocks Amphitheater
08/03/2026
USAA has created something pretty incredible.
The National Monument 250, displayed in front of the Lincoln Memorial, honors the more than 41 million Americans who have served our nation from its beginning through today.
If you, a family member, or someone you love has served, take a few minutes to look them up. It's a powerful reminder that every name represents a story, a sacrifice, and a commitment to this country.
Find your name or theirs at USAA.com/Monument250.
🇺🇸 Thank you to every man and woman who has worn the uniform. Your service will never be forgotten.
08/02/2026
Today’s Bossman Rides post is pure gratitude.
Me and my favorite Redhead made it to the top of Pikes Peak with some incredible Veterans, and my heart is still full.
What a wonderful ride. The views were unbelievable, but watching a few of these guys—Vietnam vets, 80+ years old—take on that climb with strength and stories and pride… that was something else entirely.
Incredible. Humbling. Inspiring.
This is why we ride. Not just for the summit, but for the courage it took to get here, and the legacy that still carries forward every time we show up.
Today’s picture with all of us riding isn’t just a snapshot—it’s respect. It’s gratitude. And it’s a reminder that determination doesn’t have an age limit.
Bossman rides… and this one hits close to the heart.
As the camera shows the climb to the top of Pikes Peak—just know there’s more behind every mile than mountains and miles of road.
Up there, the air gets thinner, your legs start to feel it, and you realize how real “one more step” really is. That’s what some people feel every day—only theirs isn’t a climb you can see. It’s a silent battle.
We ride for the 22+ veterans and the ones in uniform who lose their lives to su***de every day—people carrying weight no one else can fully measure.
If you’re watching this and you’re struggling, I see you. You’re not alone. Reach out. Hold on. And if you’ve got somebody in your life who seems “fine,” check on them anyway—because the fight might be happening quietly right next to you.
We made it to the top today. Now let’s keep the fight going for each other, before anyone else has to break. Part 10
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Myrtle Beach, SC
29572, 29575, 29577, 29578, 29579, 29586, 29587, 29588