Interested in events, activities and local articles, check out Attraction Magazine and Tidewater Times. These are monthly publications chocked full of fun information. Tidewater Times even provides the monthly tide table on page 43!
Speaking of water, the Talbot County public landings brochure is a helpful tool. Please check your fuel tank before you launch; yes, this comes from personal experience. There are numerous marinas and yacht clubs.
And, if you have school aged children, please call the boards of education and talk to residents in the neighborhoods that you are considering. Summer camps and after school activities are readily available. Who wouldn't like to take Sailing Class, Boat Building, Swimming or Tennis? View Chesapeake Bay Maritime Museum, YMCA of the Chesapeake, St. Michaels Community Center, Miles River Yacht Club, Tred Avon Yacht Club, Pickering Creek Environmental Center, Academy Art Museum and google County (Talbot, Caroline, Dorchester) Parks & Rec and Boards of Education.
I've grown up in this area; you're welcome to call me with questions. :)