Sunrise at the Chesapeake Bay Annapolis Maryland. Fun Fact about the Chesapeake Bay Bridge / It is one of the world's scariest bridges. According to Travel & Leisure magazine, "Drivers are notoriously afraid of this bridge, as it’s subjected to frequent—and often violent—storms. And when the bad weather hits, forget about visibility: get to the middle of this five-mile-long bridge and you can barely see land."