Duval Street has been Key West’s main street for almost 200 years, and for most of that time the town around it was getting rich, going broke or reinventing itself. This is the short version. For the street as it stands today, see our block-by-block guide.
In 1822 an American businessman named John Simonton bought the island of Key West from its Spanish owner, Juan Pablo Salas, for $2,000. Two months later the U.S. Navy raised a flag over it. In 1829 the town was surveyed and its streets laid out. Several were named for the island’s early owners, which is why Key West has a Simonton, a Whitehead, a Fleming and a Greene street. The street down the middle was named for William Pope Duval, Florida’s first territorial governor.
The money in those years came from the reef. Ships ran aground on it regularly, and Key West “wreckers” salvaged the cargo under license from a federal court. By the middle of the century the town was often described as the richest in the country for its size.
The Ten Years’ War in Cuba, which began in 1868, sent thousands of Cubans across the Florida Straits. Many were cigar makers, and they brought the industry with them. Factories opened across the island, and Key West earned the nickname “Cigar City USA.”
The Cuban community built the San Carlos Institute in 1871 as a school and meeting hall. After the Great Fire of 1886 destroyed its first home, along with much of the commercial district, the institute reopened on Duval Street in 1890. José Martí came here in the early 1890s to unite the exiles behind Cuban independence. By 1890 Key West was the largest city in Florida.
Henry Flagler’s Overseas Railroad reached Key West in 1912 and connected the island to the mainland for the first time. The 1920s brought the La Concha Hotel to Duval Street, six stories of Spanish-style stucco that still stand above everything around them.
Then the money ran out. The cigar factories had left for Tampa, the Navy had cut back, and by 1934 the city was bankrupt. Federal relief administrators decided the island’s future was tourism and set about cleaning it up to attract visitors. One side effect, noted by planners decades later, is that Key West was too poor in those years to tear down its Victorian wooden buildings. The architecture that draws people to Duval Street today survived because nobody could afford to replace it.
Ernest Hemingway was living a few blocks away through all of this, and drinking at Sloppy Joe’s. In 1937 the bar moved to the corner of Duval and Greene, where our cameras are now. The Labor Day hurricane of 1935 destroyed the railroad, and the Overseas Highway that replaced it opened in 1938.
Tennessee Williams arrived in the 1940s and is said to have finished A Streetcar Named Desire at the La Concha in 1947. President Harry Truman made 11 visits to the Little White House, a short walk from the north end of the street.
Preservation started in earnest in 1960, when residents formed the Old Island Restoration Foundation. A National Park Service survey in 1967 singled out 18 buildings on Duval as historic. Six blocks of the street went onto the National Register of Historic Places in 1971, and in 1983 the historic district was extended to cover Duval from end to end.
In April 1982 the U.S. Border Patrol set up a roadblock on the only highway into the Keys and began searching every car heading north. Traffic backed up for miles and tourism suffered. On April 23, Key West mayor Dennis Wardlow declared the island independent as the Conch Republic and declared war on the United States. He surrendered after one minute and asked for a billion dollars in foreign aid. The roadblock came down, and the town has celebrated its independence every April since. The celebration is on our events calendar.
In 2012 the American Planning Association named Duval Street one of its Great Streets in America, citing the historic buildings, the wide sidewalks and the simple fact that one street lets you walk from the Atlantic to the Gulf.
We have been watching it from the corner of Greene Street since 2000. Have a look.
