Hoping to fit in as well as anyone from Northern California can in Western Kentucky, I wore my square-toe, ostrich-and-leather Lucchese cowboy boots and faded Levi’s for my trip to cover the fifth annual Kuttawa Cannonball Run. Yeah, they were hell on my feet for a long travel day that began before sunrise and finished in the early evening, but I figured it was worth it.

When in Rome, right?

Forget this year’s record-setting 180-boat turnout. No matter how large it gets, the Kuttawa Cannonball Run will always feel homegrown. Photo by Pete Boden copyright Shoot 2 Thrill Pix.

Plus, I dig the boots. I picked them up a few years ago in Fort Worth, Texas, which for some reason makes them feel extra authentic and ups my pseudo-cowboy cred. Those boots have stories to tell. They bring back good memories.

But as I sat down to inhale a cheeseburger at HU-B’s waterfront restaurant in Kuttawa Marina with Stephen Miles, my Kentucky-based host for the weekend, second-year participant Adam Seraphine, his buddy, Mike Barnes, and a couple of other friends, I noticed something.

I was the only person in the whole damn place wearing cowboy boots. If I’d wanted to fit in, I should have worn shorts and Vans sneakers or Reef sandals, the stuff every other dude in the place was wearing.

“I like the boots,” Miles told me earlier that night as we walked down the dock to my weekend home, a 50-foot houseboat he and his wife, Heather, co-own with their friends Donnie and Cara MacLeod. “You’re going to get a lot of compliments on them.”

I didn’t get one. But I did see a few people staring at my feet and shaking their heads— and I’m pretty sure I know what they were thinking.

Why the hell is that clown from California wearing cowboy boots and blue jeans at a boating event?

To enjoy the complete 2021 Boyne Thunder Poker Run and more, subscribe to Speed On The Water digital magazine.