Williamsport was phenominal, and I went into it with exactly zero expectations because before we did that I didn't realize there was a lot of good riding up there. Keep in mind, my group is purely street because a CB1100 does NOT mix well with gravel and fire roads and trails, but we found some badass roads, pretty much everywhere between the Corning museum and the flight 93 memorial. Our rallies are usually an entire week, so we range all over. I even took a solo morning up the Worlds End state park and even that was a good time.
I think the key to these events is not just location but lodgings....The place has got to appeal to all comers, it's got to be affordable, and not a terrible dive that nobody wants to stay in. Campgrounds are cool, but only to people who like camping. Some cities are just awful for lodging prices, while some are like untouched paradises. The next key element is a GUIDE. somebody has to take charge and who knows the area like the back of his hand. a good small bike rally is kind of a tour of the area put on by a person who's proud of his stomping grounds. That also means there's solid and well thought-out routes on the books that everybody can follow. I've been to rallies where it's just everybody kind of grouping up on their own and going in different directions in the morning and it doesn't really work out well. having a couple groups with distinct ride styles in mind is a good plan. a free for all is not.
i realize i'm talking a lot of noise without saying "heck i'll do it" but that's because of the point I made above...Charleston is a shit place for a rally. All our roads are stick straight and boooooooriiing. We DO have a lot of trails and whatnot, and the town itself is a fantastic place to visit and especially a fantastic place to eat, but I Don't know if that makes a rally. Then again, i'm still thinking from the point of view of somebody riding a big 4 cylinder street bike and not the point of view of somebody riding a 125cc trail bike. maybe people with more experience on that kind of bike could tell me i'm wrong about charleston being a shit place for a rally, at which point i would be more than happy to show you every nook and cranny of this town and help plan/scout routes.