When established in 1823 Monroe County occupied most of the southern Florida peninsula; it has since been reduced to the Florida Keys and portions of Everglades National Park. It was founded during the "Era of Good Feelings" and named for President James Monroe. The county seat is Key West, once the largest city in Florida despite its isolation. Although it is the westernmost of the inhabited keys, the name is actually a corruption of cayo hueso, "bone island." Early Spanish explorers reported a number of human skeletons on the island, possibly left after a battle between tribes.

     Monroe County residents originally were required to travel all the way to St. Augustine for court sessions. The Monroe County historic courthouse was built in 1890 by William Kerr, who was also responsible for such other memorable buildings as the Convent of Mary Immaculate (later demolished), First Methodist Church, post office, and city hall. The hundred-foot clock tower, with an observation deck atop, was for a long time the highest point on the island.