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. 🇺🇸

05/30/2026

Tonight at the The KillBox Comedy Club Mope Williams Wild N Out get your tickets now at Thekillboxcomedyclub.com

The Favorite Redhead is still slinging Raffle Tickets for the '99 Road King.  I'll be at KimTam Park at Melanie Springs ...
05/29/2026

The Favorite Redhead is still slinging Raffle Tickets for the '99 Road King. I'll be at KimTam Park at Melanie Springs all weekend!! Don't wait for Wed!!

What a great turnout yesterday for the FIRST Boss Man Rides Bike Night of the season at Kim Tam Park! 🔥We had an awesome...
05/28/2026

What a great turnout yesterday for the FIRST Boss Man Rides Bike Night of the season at Kim Tam Park! 🔥

We had an awesome group, a ton of energy, and some really cool ideas already cooking for what’s coming next. One of the big things we’re building is a timer set-up for the Slow Ride—we’ll be tracking it nightly and throughout the whole season, with prizes for the riders who bring it.

And I want to give a huge shout-out to robmylender.com for sponsoring this event—without you, it wouldn’t have been this cool. Thank you!

Looking forward to many more Wednesdays and a full season of great rides with great people! 🏍️💨

Come see Icie! The Favorite Redhead will be selling raffle tickets, and her Harley merch! Come Ride!!
05/27/2026

Come see Icie! The Favorite Redhead will be selling raffle tickets, and her Harley merch! Come Ride!!

Hope to see ya out today
05/27/2026

Hope to see ya out today

Any vendors except food trucks can set up FREE for our first BIKE NIGHT with Dave Jackson singing great songs Bob's Hamb...
05/26/2026

Any vendors except food trucks can set up FREE for our first BIKE NIGHT with Dave Jackson singing great songs Bob's Hamburg on Wheels serving up delicious burgers and $1 beers. We will have biker games and sponsored by Melanie's Gifts and Rob Dawson Robmylender.com

1st Bike Night Happy Hour 5:30-6:30 DOLLAR BEERS!! Sponsored by Robmylender.com
05/26/2026

1st Bike Night Happy Hour 5:30-6:30 DOLLAR BEERS!! Sponsored by Robmylender.com

05/26/2026

🚨 BOSS MAN RIDES BIKE NIGHT — WEDNESDAY! 🚨

This is our first Bike Night of the year, and we’re kicking it off the right way.

🔥 Biker Olympics are happening
🎤 Entertainment by Mr. Dave Jackson
🍔 Bobs Hamburg Truck Festivities kickoff around 6:00 PM until who knows when!
2881 Canton Road Uniontown Ohio 44685
KimTam Park at Melanie Springs

And that’s not all—keep your eyes on the prize:
🏍️ We’re raffling off a really cool Road King loaded with tons of extras!

🎥 Here’s a video of the Road King you could win—watch it, lock in your spot, and get ready for a great night.

We definitely are missing our seat time.
05/20/2026

We definitely are missing our seat time.

Address

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

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