I've been involved with a Progressive Dinner for several years. This is an event where you go to one house and eat appetizers, go to another house and eat salad, next house and eat main course, last house and eat dessert. The problem is you get totally bloated by the time you're done. Solution: Do it on bicycles with about 10 miles between houses. (We've done this as a Christmas thing, by the way, with a gift exchange at the end).

Go to these organized rides and everyone is there on the latest bike, mostly road-type bikes. How bout an event specifically for single-speed-cruiser bicycles? This assumes the course is not too hilly, and you need to give everyone enough time to scrounge up their bicycles. Either $60 at Walmart or less at a garage sale or CL or whatever. The point is that it would be something different. You could make this a "50's Ride" and wear clothing from the 50's or period of your choice as well.

You have the Hawaiian ride up there already. Suggestion: Bicycle to a public swimming pool or lake, give everyone a chance to take a dip before getting back on the bikes. Might take some arranging with the city or whoever (getting reservations for a pool, etc. And let them know a bunch of sweaty people will be jumping in- they may not like that). This could also be a Swimsuit Ride if things didn't get too out of hand.

The few group rides I've been to, everyone had on their full cycling gear. So how bout a "Jeans and T-Shirt" ride or something along that lines to get people looking a bit less like the typical cyclists?

The Tom Sawyer Ride- everyone takes their cane poles and goes fishing!