A stop in historic Chesapeake City means you’ve made it halfway through the C&D Canal. Ship watching on the third busiest canal in the world is the favored pastime; waterfront bars and restaurants encourage this practice. Huge ships clear the 140-foot high Chesapeake City Bridge with awe-inspiring ease. The constant parade of ships and boats provides incredible photo-ops, from international cargo ships, working tugboats and barges, and fabulous mega-yachts to sailboats and classic tall ships. 

Dutch mapmaker Augustine Herrman first suggested building a canal across the top of the Delmarva Peninsula in the 17th century. By the 1760s, surveyors were scouting routes. Construction of the current canal began in 1824, and it opened in 1829. The route cuts 300 miles off the maritime route from Baltimore to Philadelphia. The canal, a 14-mile shortcut between the Delaware River and the Chesapeake Bay, bisects the town into north and south sides. The Victorian south side is a tiny jewel box that grew into Chesapeake City once the shovels hit the dirt in the early 19th century for canal construction. Chesapeake City grew up around the canal, and many buildings left over from the early days still stand.