I did the Ride to See last August and it was great.
Cheap ($30), benefits a good charity (Lion's Charity Programs for vision health), was small (something like 200 riders), well supported by super friendly folks (on a first name basis with many of them by the end of the day), and the terrain was surprisingly wonderful for the Eastern Shore. I never knew there were rolling hills to be had out there. Oh, it passes through Rock Hall during their Pirates and Wenches Fantasy Weekend so you could practice your "Arrrgghh's" while stopping at a rest stop. Super fun and while it slowed down the pace a bit last year, added more than a little bit of fun to an already great ride.
I'll be there this year too and hope to see some of you!