However you define "classic," it's probably here.
Vintage Motofest is a combined weekend of AHRMA Vintage Racing and what used to be a Milwaukee-based bike show called Rockerbox. A few years ago, Rockerbox moved from Milwaukee up to Road America in Elkhart Lake, Wisconsin. If you went to it back when it was a street festival, the best part about Rockerbox was that there was literally everything there.
From crazy customs to rat bikes to pristine, gorgeous vintage bikes, to builds that defy any sort of easy description—even if you couldn’t name it, you could probably see it there. Rockerbox was the ultimate in sensory overload, in the best sort of way. If you were lucky the sun was shining, Fuel iced coffee and/or your favorite beer (New Glarus, what is UP?) was flowing, and a good time was had by all.
After the fest moved away from Milwaukee, it’s probably no surprise that it changed. It became more solidly about vintage bikes, and less about everything bike-related that you could possibly ever want to cram into your eyeballs. Opinions as to whether this is a good thing or not will, of course, vary.
The other thing I’ve noticed is that the actual ‘show’ part of the show has gotten smaller. However, people attending still ride some amazing stuff into America’s National Park of Speed. As such, it was incredibly difficult to narrow this list down even as far as I did. I’m gonna tell you right now, these aren’t really ranked. They’re just all amazing, and how do you choose a best when they’re all this good?