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Saint Paddys Parade Pub Crawl Chamber Featured Event Saturday March 15 12PM Chesapeake City is located along one of the busiest canals in the world. As early as the 17th century local settlers including the famous surveyor and map maker Augustine Herman recognized the possibility of connecting the Chesapeake Bay with the Delaware River. Chesapeake City is currently the only town in Maryland that is situated on a working commercial canal. Most of its interesting 19thcentury architecture remains intact and the area that encompasses it on the south bank has been placed on the National Register of Historic Places.