Drive the Overseas Highway and you pass all of it without seeing any of it. Coral rock ruins in the mangroves, concrete arches marching out to sea, a monument by the roadside at mile marker 81.6. These are the stories behind them.
- 1513–1700sLos Martires
Spanish sailors name the low, jagged islands "the martyrs" for their appearance from the deck. For two centuries the Keys are a hazard to be survived, not a place to live — though wrecked galleons begin salting the reef with silver as early as the 1540s.
- 1822Key West becomes American
The island is sold to an American businessman and the U.S. Navy arrives to clear out piracy. A scruffy harbor town of Bahamian, Cuban, English, and New England mariners begins to organize itself.
- 1828–1850sThe wrecking era
A federal Admiralty Court in Key West makes salvage a licensed, regulated, and extremely profitable industry. Key West becomes the wealthiest city per capita in the United States. Read the full story →
- 1860s–1890sSponges, cigars, and Cuba
Lighthouses end the wrecking boom. Sponging takes over, then cigar-making: Cuban immigrants turn Key West into the cigar capital of the world. José Martí raises support here for Cuban independence.
- 1905–1912Flagler's Folly
Henry Flagler builds a railroad 128 miles across open ocean to Key West. Seven years, more than 4,000 men, five hurricanes. The first train arrives January 22, 1912. Read the full story →
- 1928–1940Hemingway's decade
Ernest Hemingway settles on Whitehead Street, writes some of his best-known work in a loft above the garden, and starts a dynasty of six-toed cats. Read the full story →
- 1935The Labor Day Hurricane
The most intense hurricane on record to strike the United States comes ashore over the Matecumbe Keys. Hundreds die, including WWI veterans in federal work camps, and the railroad is finished. Read the full story →
- 1938The Overseas Highway opens
The state buys the ruined railroad and converts Flagler's bridges to carry automobiles. The road trip that defines the Keys begins.
- 1963America's first underwater park
John Pennekamp Coral Reef State Park opens at Key Largo to protect the only living barrier reef in the continental United States. More →
- 1982The Conch Republic
A Border Patrol roadblock strangles the highway. Key West secedes, declares war, surrenders in about a minute, and requests foreign aid. The roadblock comes down. Read the full story →
The long reads
1905–1935 · The Railroad
The railroad that went to sea
How a 75-year-old oil millionaire built the impossible across 128 miles of open water — and where you can still walk on it today.
September 2, 1935 · MM 81.6
The Labor Day Hurricane
The strongest storm ever to hit the United States, the veterans' camps, and the rescue train that arrived at exactly the wrong moment.
1820s–1850s · Key West
The wreckers
Salvaging ships off the reef was legal, court-regulated, and lucrative enough to make this the richest city in America.
1928–1940 · MM 0
Hemingway's Key West
The house, the books, the pool that cost him his last penny, and the truth about those six-toed cats.
April 23, 1982
The Conch Republic
The day Key West seceded from the United States, declared war, surrendered, and asked for foreign aid.
MM 106 → MM 0
The mile marker guide
What's at every marker on the Overseas Highway, and how to read the Keys' address system like a local.