There is the Good Old Boat Regatta every year just after the Sailboat show. There are many evening races during the summer in which old and new boats run around the course. There are races for those who are not so competetive and those who are die hards. Being near Annapolis, you will have no shortage of races. I am not a racer myself, but I am sure somebody here can point you in the right direction.
Small Tits Cam