Yep, every year the classic and cafe racer club here in Orange does a ride. We get dressed up, get on our oldest or strangest bikes and do a loop of the city then go for coffee.
The organisation has raised a fair bit of money. They take a huge fee out of it but I suspect about the same as any charity ..... but hell .... we get to have some fun.
I usually wear white tie and tails, others tweed hunting style stuff and donate $20 or so.
This is a truly great event. I've ridden the past three years in Asheville and saw a Rocket there one year (that guy joined this forum, but is apparently MIA). Anyway, I've always taken the '98 Thunderbird Sport, as they do prefer more classic bikes. The Asheville organizers aren't very strict about that, so I may ride the Rocket this time, if my wife decides to come along.