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Getting to the Keys - Then & Now, pt. 1

Henry Flagler was a man with a vision. Born in New York, he went to work following the 8th grade. He worked his way up, eventually marrying his boss’s daughter, Mary. Mary had continuing health problems which were what brought Flagler to Florida.

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His partnership with John D. Rockefeller in 1867 emerged as Standard Oil Company. By age 50, he was one of the wealthiest men in the world. For Mary’s failing health, the couple journeyed to Jacksonville, Florida during the winter of 1867-68. It was the first of many trips to Florida, a state which Flagler made his personal project for the rest of his life. Even after Mary died, Flagler continued to return to Florida. He bought a railroad and by 1896, his railroad had made it from St. Augustine to Biscayne Bay in Miami.

In 1905, at 75 years of age, Flagler began his most daring enterprise yet – the job of extending his railroad to Key West, at the time the largest town in Florida and the closest American city to the new Panama Canal.

This project, nicknamed "Flagler's Folly", seemed impossible at first and indeed was monstrously difficult. More than 4,000 men worked on the railroad. Sand flies, mosquitoes (there was no yellow fever vaccine) and hurricanes continually plagued the workers. Everything had to be brought in by barge - materials, equipment, food, water.

Seven years later, on January 22, 1912, the first New York to Key West train arrived in Key West, carrying Flagler & his third wife. It was his only trip to Key West on his train. He died May 20, 1913. His vision died September 22, 1935. In those 23 years, an estimated 50 million passengers made the trip to Key West.

September 22, 1935 - Labor Day. One of the most destructive hurricanes to ever hit the United States struck. Flagler’s tracks were washed away in many places. The train itself was destroyed by a surge of water over 17 feet high while attempting to evacuate families from Islamorada. Train, families and homes all disappeared. Five hundred bodies were eventually found, but there will never be an accurate accounting of the lives lost that day.

Flagler’s Folly was gone. Access to Key West was back to boat only. But Key West & its inhabitants were tough and determined to not only survive, but prosper.


  • keithlk 4 years ago

    I don't believe that almost 6000 passengers a day made the trip to Key West

  • Wendy 4 years ago

    I have wondered about the number myself but I do know that they had more than one train a day going. I also wonder if that isn't a count of ticket sales, including someone going from, say Islamorado to Marathon. I will research it some more.

    Thanks for reading.