Small Peninsula Community of nearly 1000 homes located between the Chesapeake Bay and the West River. The peninsula has a rich tradition of working on the Chesapeake Bay. It contains several small communities that each have unique views of the water. The Shady Side area is not to far from the Annapolis, Washington and Baltimore metro areas. If you enjoy small town living and the Chesapeake Bay then the Shady Side Peninsula is a must see!