Bossman Rides

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. 🇺🇸

This Wednesday is going to be another great Boss Man Rides Bike Night at Kim Tam Park!We want to give a big thank-you to...
09/02/2026

This Wednesday is going to be another great Boss Man Rides Bike Night at Kim Tam Park!

We want to give a big thank-you to Ronald Joseph III, owner of Triple R Auto Glass LLC, for stopping in and sponsoring our brand-new Bike Night contest. Ronald has put up a $100 cash prize for the winner!

We’ll also be giving away:

20 free passes to The Kill Box Comedy Club
One 2027 Kim Tam Park season pass
Come enjoy a few hours with us, listen to the live music from Dave Jackson, and take part in the fun. Whether you ride a motorcycle, bicycle, tricycle, three-wheeler, or motorized bicycle, everyone is welcome. No special skill is required—just come down and enjoy yourself!

Bike Night starts at 5:30 p.m. at Kim Tam Park at Melanie Springs.

Thank you again to Ronald Joseph III and Triple R Auto Glass LLC for supporting our Bike Night community. We’ll see you Wednesday!

09/01/2026

Every Wednesday night is Boss Man Rides Bike Night!

We kick things off at 5:30 PM, and in this video, I’m explaining how our game works. The best part? There’s really no skill required—and you don’t even need a motorcycle to participate!

Bring your bicycle, tricycle, three-wheeler, or anything you can ride. Everyone is welcome, and we’re planning a fun, entertaining night for the whole crew!

We’ll also have Dave Jackson playing your favorite Bike Night tunes, so bring your friends, enjoy the music, and come join the fun!

Kim Tam Park at Melanie Springs
2881 Canton Rd., Uniontown, Ohio

Today is a truly special day at Boss Man Rides.We’re getting ready to put up the American flags for our local Rotary gro...
09/01/2026

Today is a truly special day at Boss Man Rides.

We’re getting ready to put up the American flags for our local Rotary group, and this year means even more because my son is joining me for the very first time.

Standing beside him among these flags is a moment I’ll never forget. Patriotism isn’t just something we talk about, it’s something we live, teach, and pass on. Every flag represents freedom, sacrifice, service, and the brave men and women who have defended this country.

At Boss Man Rides, we also ride in honor of the 22 veterans and one active-duty service member we lose each day to su***de. The 22+1 are never forgotten. Their lives, their service, and the battles many face in silence matter deeply to us.

Today, as we raise these flags, we’re honoring every veteran, every service member, every family, and every American who has sacrificed for the freedoms represented by these colors.

I’m proud to serve alongside my son, proud to serve our community, and proud to carry the message that we ride with purpose—for freedom, for those who served, and for the 22+1.

From our family to yours, God bless America.

Please like and share the Boss Man Rides page and help us keep the conversation going.

08/31/2026

Some rides stay with you forever.

When I was 16 years old, I had my very first street bike—and that motorcycle opened the door to memories, lessons, friendships, and adventures I’ll never forget. One of those unforgettable rides was the trip from Ohio to Daytona. Looking back, it wasn’t just about the miles we traveled. It was about the freedom, the excitement, and the feeling of being out there chasing the next adventure.

In this video, I’m sharing a little about that first street bike and the ride that helped shape my love for motorcycles and the open road.

What was your first motorcycle?
How old were you when you started riding?
What’s one ride or road trip you’ll never forget?

Share your stories in the comments. The Boss Man Rides family is built on the memories we make, the roads we travel, and the people we meet along the way.

If you enjoy motorcycles, road trips, memories, and real conversations, follow and like the Boss Man Rides page. Let us know what topics you’d like to hear about in future videos—bike builds, long-distance rides, motorcycle history, riding tips, events, or stories from the road.

Like, share, and invite your friends to be part of the Boss Man Rides family.

The Goodyear Blimp made a special appearance over Boss Man Rides HQ this weekend, and we couldn’t pass up the chance to ...
08/31/2026

The Goodyear Blimp made a special appearance over Boss Man Rides HQ this weekend, and we couldn’t pass up the chance to capture a picture of it!

It’s not every day you see the blimp flying over our area, so this definitely turned into an unexpected photo op. Have you ever seen the Goodyear Blimp in person? Where were you when you saw it?

Drop your blimp stories in the comments, and be sure to like and share the Boss Man Rides page with the family!

08/30/2026

Today was a pretty epic day here at Boss Man Rides HQ! We had the pleasure of hosting the Akron Bible Church summer picnic, and the kids were definitely making the most of the day—laughing, playing, and having a blast.

This video has to be one of the most epic flip fails I’ve ever seen. He went for the flip, rotated a little too far, and absolutely smacked the water face-first! Thankfully, it turned into one of those unforgettable moments everyone will be talking about.

What do you think—was this a failed flip or a legendary attempt?

Tomorrow, Boss Man Rides HQ at Kim Tam Park at Melanie Springs will be the place to be for a special Sunday with Akron B...
08/29/2026

Tomorrow, Boss Man Rides HQ at Kim Tam Park at Melanie Springs will be the place to be for a special Sunday with Akron Bible Church.

ABC Church is holding its yearly picnic at Boss Man Rides HQ, beginning with a church service at 10:30 a.m. In the afternoon, they’ll celebrate baptisms—a powerful time of faith, renewal, and new beginnings.

The entire Boss Man Rides family is welcome to come out, enjoy the day, support those being baptized, and share in this special gathering. If you’ve been thinking about being baptized, come on out and take that next step.

Temperatures are expected to reach the high 80s, making it a perfect Sunday to gather with friends, enjoy the park, and make more memories together.

The Boss Man loves you all. We’ll see you Sunday at Boss Man Rides HQ!

Tonight’s the night at The KillBox Comedy Club!The Boss Man is giving away FREE tickets to see Michael Winslow, the lege...
08/29/2026

Tonight’s the night at The KillBox Comedy Club!

The Boss Man is giving away FREE tickets to see Michael Winslow, the legendary star of the Police Academy movies and master of sound effects!

It’s a great show you won’t want to miss. Grab your tickets now and use the promo code below:

Get your free tickets at Thekillboxcomedyclub.com and come check out Michael Winslow live tonight!

kry

08/28/2026

Incredible

What Pat accomplished is absolutely incredible.Congratulations to Vroom Old Man - Indian 125+ for Myotonic on earning hi...
08/28/2026

What Pat accomplished is absolutely incredible.

Congratulations to Vroom Old Man - Indian 125+ for Myotonic on earning his Atlas World Records awards for Myotonic Dystrophy. As a rider, I understand the dedication it takes to put miles behind you—but 201,901 miles on one motorcycle in that short time frame is beyond anything most of us can truly comprehend.

That isn’t just riding. That’s commitment, sacrifice, endurance, and a level of determination that deserves every bit of recognition.

Pat spent countless hours away from his family, slept beside the bike, pushed through exhaustion, and fueled the journey with whatever was available along the way. Apparently, those Love’s roller dogs that he loves were so effective that on my last ride, I must’ve had five of them myself. Maybe they really are motorcycle fuel after all.

But Pat’s mission was about far more than riding. He took on this incredible challenge to raise awareness and funds for people affected by Myotonic Dystrophy.

From the Boss Man Rides family to motorcycle enthusiasts everywhere, this is a story worth supporting. Riders understand what it means to keep moving when the road gets long, the hours get late, and the body starts telling you to stop. Pat pushed that spirit farther than most of us could ever imagine.

Now he’s working toward matching the mileage on the bike—201,901 miles—and every contribution can help.

If you’re able, visit Pat’s page, learn more about his mission, and donate
1, 2,5,10$ or whatever you can. When the riding community comes together, even small contributions can create a meaningful impact.

Huge congratulations, Pat. Your journey is unbelievable, your dedication is inspiring, and your mission proves that the miles we ride can make a difference far beyond the road.

Keep rolling, brother.

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Myrtle Beach, SC
29572, 29575, 29577, 29578, 29579, 29586, 29587, 29588

Telephone

(330)3107661

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