Henry Flagler and the Last Train to Paradise

By Gerry Barker

It’s a classic case of they said it couldn’t be done.

It started in the 1870s, when Henry Flagler, founder of Standard Oil and one of America’s wealthiest Gilded Age titans, sought a warm climate for his ailing wife and discovered Florida.

Realizing its potential as a vacation mecca, Flagler built a string of resort hotels all along Florida’s east coast, from St. Augustine to Palm Beach and south to Miami, and also constructed a railroad — the Florida East Coast Railway — to connect them. But why stop in Miami, when tropical Key West beckoned.

Photos by Gerry Barker

Build a railroad over 100 miles of open ocean and land? Critics called it “Flagler’s Folly.” The story of what became “the eighth wonder of the world” is the subject for best-selling author Les Standiford’s book, “Last Train to Paradise,” which he, along with the founder of Miami-based Books & Books, Mitchell Kaplan, talked about during a recent lecture on the sailing yacht, Sea Cloud Spirit.

When asked why he chose Flagler’s railroad for a book, Standiford said, “In truth, it’s better than anything I could dream up on my own. One of the richest men in the world undertakes the engineering challenge of the century … Just imagine the Golden Gate bridge stretching for 150 miles.”

He talked about the sacrifices of the men doing the day-to-day work. “Over the course of the seven years it took to build it, hundreds died. They chased alligators off barges every morning just to go to work.”

Today, it’s hard to imagine just what Florida was like back in the mid-1800s. Standiford said if you drew a line from Jacksonville to Tampa, south of the line was virtually “terra incognito.” “There were no roads, no houses, no settlements.” At that time, the state’s most important city was far and away Key West, a thriving port and naval station.

Flagler reasoned Key West would be the closest Eastern port from the Panama Canal. Once a deep water harbor was dredged, ships would come to Key West to refuel with coal, and their cargo would be transported across the U.S. via railroad. But by the time his railroad was finished, neither scenario came to pass.

“Part of what fueled his ambition to build it was he had gotten sick and tired of people telling him it could not be done,” said Standiford.

It’s easy to imagine the attraction of a trip on the Overseas Railroad. “The train became known as the scenic route to Havana,” he told the audience. “You would get on your sleeping car at New York’s Penn Station at 5 pm. Three and a-half days later, you could be in that same car riding the rails in Cuba.” That’s because once the train arrived in Key West, your Pullman car would be taken by ferry 90 miles to Cuba, offloaded to a Cuban train and you would be ready to tour the island.

The railroad to Key West, started in 1905 and finished in 1912, never made a dime, said the author, but people loved it. When the train stopped at a drawbridge, “passengers took out their fishing poles.” Also, “schools of dolphins would chase the shadows of the train.” Riders couldn’t tell they were on a bridge — they could only see water on either side and the dolphins.

So what happened to this marvel of engineering?

Some of is still there — segments of the original bridges built between 1905 and 1912. But the great hurricane of Labor Day, 1935, swept most of it away. With winds estimated at 200 MPH, the train was hit by a 20-foot tidal surge. Standiford said three people on the train survived: The engineer, conductor and brakeman — all huddled in the cab of the 450-ton locomotive “even the hurricane couldn’t displace.”

Standiford was able to talk to one of the storm’s survivors, who was 12 at the time. Out of 63 family members, all farmers and pineapple farmers, he was the only one left alive.

Flagler died a year after the train project was completed — May 20, 1913 — at the age of 83. He took great pride in what he created. “At one point,” said Standiford, “he just stopped being interested in making money and became more interested in doing things that he thought were worthwhile.”

While railroads may come and go, Flagler’s legacy lives on in the state he virtually put on the map.