The drive in idea is interesting, but it absolutely has to be designed so riders can get back to their cars without going on the street after dark. At least if I understand the demographic right.

Maryland right?

Thinking of the club rides I have gone on the closest to theme is when the rest stop is a significant place toe eat, where the eating is part of teh reason for the ride.

My first computer job was with a company based in Maryland. On a trip to headquarters the local marketing office took us to a perfectly dreadful Maxican resturant. The techies more than made up for it by taking us to a great all you can eat seafood place.

Any place at the beach or at least with a nice outdoor area that might be up for seafood service for bikers? Heck you can fold that into the pirate ride to give 2 reasons to ride.