The Chesapeake Bay Bridge Bringing the Western & Eastern Shores Together When it's summertime in my neck of the woods this usually means a jaunt across the Cheasapeake Bay Bridge to the Ocean.. Back before the bridge was built in 1952 a ferry was the only way to the Eastern Shore side of the Chesapeake Bay. With the bay stretching for 4+/- miles from shore to shore not many ventured in that direction and instead the beaches on the western side became the playgrounds of DC and Baltimore. Summer homes were a norm right here around Annapolis as people came to (5 comments)