Bossman Rides

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

06/18/2026

Breaking Records at Bossman Rides HQ

Last Saturday at Kim Tam Park (Melanie Springs) was one for the record books! The Backwoods Bash brought out an incredible crowd—so many families, friends, and good vibes that we’re now in the middle of counting and confirming the numbers. 📍🌲

Right now, everything is pointing to one thing: we may have broken a record dating back to the 1950s. That’s pretty wild.

Huge thanks to the Backwoods Bash Club for bringing your event out to the Park and helping make the day feel even more special here than ever. You brought the energy—Kim Tam Park brought the memories.

Stay tuned for the drone footage… because you’re not gonna believe how awesome it looks from above. We’re getting the footage ready and we’ll share it shortly.

If you were at the Park last Saturday, drop a comment with your favorite moment from the day—let’s relive it together.

— Bossman at Kim Tam Park

06/17/2026

Bike night for tonight, June 17th, is canceled! Raffle drawing will be next week, we have 11 tickets left!

06/17/2026

The Road King gets raffled off tonight at Bike Night. Last chance for a ticket 12 left.

Photos from Bossman Rides's post 06/16/2026

Just picked up this 1971 Honda 100. 🏍️
Now I’m putting on street tires so it’s ready to make some miles.

And yes—if all goes right—this little machine is going to be rode to Sturgis.

This is going to be a voyage of fun: throttle time, roadside memories, and a ridiculous amount of “how are you pulling that off?” moments.

Follow along—Boss Man Rides is officially setting a small-bike, big-adventure plan. Let’s ride.

06/15/2026

Our BIGGEST sponsor
🎤🔥 THIS WEEK AT THE KILLBOX! 🔥🎤

🚨 ED BASSMASTER TAKES OVER! 🚨

The internet legend with over 2.8 million YouTube subscribers, viral characters, hidden camera pranks, and the famous “Would ya look at that!” catchphrase is here for THREE NIGHTS ONLY!

😂 Thursday, June 18
😂 Friday, June 19
😂 Saturday, June 20

Tickets are moving fast, so don’t wait until the last minute and risk hearing about it from your friends on Monday.

👔 Father’s Day Weekend Continues! 👔

On Sunday, June 21, we’re wrapping up the week with headliner Chevy Terrill and a special Father’s Day VIP Dinner Package that includes:

✅ Preferred Seating
✅ Dinner Included
✅ Two Drinks Included
✅ Comedy Show Ticket

Treat Dad to something better than another tie he’ll never wear.

🎟️ Grab your tickets now at:

https://www.thekillboxcomedyclub.com

06/15/2026

🏍️ Bike Night • Wednesday • KimTam Park 🏍️

🍺 $1 beers from 5:30-6:30 thanks to Rob My Lender, Rob Dawson.

Dave Jackson. Slow Ride Contest. Bike Raffle. Good people. More vendors.

Still room for vendors—contact the Favorite Redhead, Jo Bayer.

Who's riding in? 🔥

06/10/2026

Get ready, Bossman Crew—every Wednesday at Boss Man Rides Bike Night we turn the roads into a good time, and this week is about to be extra awesome.

This Wednesday’s Special Exhibition
We’re rolling out the lineup for an epic exhibition featuring Raining Bobs Hamburg, the Food Eating Champ, and Mr. Mike England—aka “Mike the Beef.”
It’s going down at 6:30 PM, and if you’ve never seen this kind of action up close, you’re in for a treat.

Details
Where: Boss Man Rides Bike Night KimTam Park at Melanie Springs
When: Wednesdays
Start: 6:30 PM for the exhibition
Happy Hour: Sponsored by Robmylender.com starts at 5:30
Come Ride With Us
Pull up early, bring your crew, and come watch something amazing happen. Let’s make this Wednesday one for the books—see you there at Boss Man Rides Bike Night.

06/10/2026

Every Wednesday BIKE NIGHT happy hour starts at 5:30 at KimTam Park at Melanie Springs

06/09/2026

🇺🇸 Every veteran has a story.

A few days ago, our friend Bruce was metal detecting at KimTam Park when he uncovered a Marine Corps dog tag that had been buried for who knows how many years.

We knew one thing immediately: it needed to find its way home.

With the help of social media, friends, veterans, and complete strangers willing to share a post, we tracked down the Marine's family. The Marine now lives in Connecticut, and today his father rode his Harley to pick up the dog tag on his behalf.

What started as a small piece of metal became a reminder of something bigger: we don't leave our veterans behind.

Thank you to Bruce for finding it, to everyone who shared the original post, and to the Marine family for allowing us to be a small part of this reunion.

Some things are worth the effort.

🇺🇸 Semper Fi.
🏍️ Bossman Rides

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