I don't know how strong the Catalina 27/270 Association is, but if it is only 1/2 as good as the C-34 owners association, it will be great.Welcome to SailNet. We keep our Catalina in Rock Hall. There are a couple of Kent Island SailNetters. Best of luck with your boat.
You might consider joining one of the Catalina owners associations. Lots of support.
International Catalina 27/270 Association
Chesapeake Catalina Yacht Club - Sailing in the Cheasapeake Bay
The Chesapeake Catalina club is active and when we were members (more than likely renewing for 2015), we received a lot of help and encouragement.