I thought about that too- I've been to Sturgis twice. The first time I went, we were headed for Mt. Rushmore and had NO idea what the Sturgis Rally was or how many bikes would be on the road- they were literally everywhere, and there were no hotels. We had to sleep in the car, really! The second time I got there ahead of time and got a room. Didn't see the rally but lots of bikes at the Wall Drugstore!
Traveling in that direction, you will pass hundreds if not thousands of bikers. As you watch them go by, you notice that hardy any of them wear helmets, so you could see their faces really well. I'd just keel over if I saw Larry, I might follow him, though he'd just tell me to FOAD I bet. I would take a pic and post it here though.
I really don't think the celebrities take the chance of the long road trip on the bike. They are probably among what I call the 'lazy' bikers, the ones who ride a big fancy truck or van and pull the bike behind them on a trailer for when they get there. With all Larry's money he might even just fly in and have his bike shipped or ridden by someone else, but would he trust them?
Being he is the big Harley fan, I have to believe he's been there at least once, it is 'hog heaven'
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~"A little out of touch, little insane, just easier than dealin' with the pain!" ~Soul Asylum, "Runaway Train"