The Annapolis Yacht Club on Spa Creek near the bridge that connects Annapolis and Eastport sponsors the races. You may want to check out the web site or contact the club. I am sure that skippers are always looking for "rail meat," which doesn't require much experience. Spinsheet magazine is also a source of info about racing in and around Annapolis.
http://www.annapolisyc.com/
http://www.spinsheet.com/