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Henry Flagler's dream, the Over-Sea railway, came true 100 years ago, connecting Miami to Key West

This is a map of the Florida East Coast Railway from the book Last Train to Paradise.
This is a map of the Florida East Coast Railway from the book Last Train to Paradise.
Published Jan. 24, 2012

Flagler's Folly.

That's what the smart set called Henry Morrison Flagler's ambitious plans for a railroad across the sea. Was the rich old man demented? Did he really think he could extend his Florida East Coast Railway from Miami through the swamps and over open water to Key West?

Of course he did.

Born in Hopewell, N.Y., in 1830, Flagler grew up poor, dropping out of school after eighth grade to work in a grain store for $5 a month. By 1867, he was John D. Rockefeller's business partner and later a founder of Standard Oil.

From there, Flagler became the man who invented modern Florida.

He first visited our state in 1878, hoping the fair weather in Jacksonville might enhance his wife's ill health. After her death, he brought wife No. 2 to St. Augustine in 1883. He liked the town, but thought it lacked decent lodging and transportation. Flagler being Flagler, he built the grand Hotel Ponce de Leon (now Flagler College) and acquired a railroad.

He spent the next decade extending tracks south so tourists could take the new train to any number of new Flagler hotels under construction. Even before the tracks reached Miami in 1896 Flagler was wondering about the possibility of going even farther.

There was no road to Key West, the state's most prosperous city thanks to the cigar industry, much less a lot of dry ground for railroad tracks.

Flagler, who hadn't gotten rich by being cautious, told people his Key West dream. "Kooky talk," was the consensus. A railroad couldn't be built to Key West, the smart set told him, because of the swamps and soft bottom and snakes and crocodiles and sharks and mosquitoes and unreliable labor, long bridges over deep water and hurricanes.

Henry Morrison Flagler was a craggy, white-haired business genius who hated hearing that his ambitious plans were unattainable. He also hated passing up a chance to add millions more to his bank account.

Key West, among other things, was the nation's southernmost deepwater port and the gateway to the tropics, including Panama, where a new canal to the Pacific was under construction. Flagler's train would arrive in Key West carrying tourists who would stay at Flagler's proposed new hotel and perhaps board a ferry for a trip to Havana.

One hundred years ago today, a wood-burning locomotive chugged into Key West towing five cars, including one with a copper roof, wood-paneled lounge, bath, kitchen and private stateroom.

The train rumbled to a stop. Flagler, 82, stepped out of his private car with wife No. 3, half his age but happy to bask in the applause of more than a thousand spectators.

"Now I can die happy,'' Flagler whispered to a friend. "My dream is fulfilled.''

The smart set? Now they were calling "Flagler's Folly" the "Eighth Wonder of the World.''

It's gone now, of course, gone with the wind from the most powerful hurricane to ever strike the United States. In 1935 the famous "Labor Day" storm swept over the Keys with 200 mph winds, killed hundreds and demolished the railroad.

Three years later, a new highway was completed to Key West. The new road was placed atop what remained of the old railbed and across the old railroad bridges.

In the 21st century, many Floridians know nothing about the railroad that opened the Keys to tourism, the man who built it or the storm that swallowed it up.

• • •

It was one of America's great engineering achievements.

The 51-mile Panama Canal was 34 years in the making. Flagler's 153-mile Over-Sea Railroad from Miami took seven years. Flagler being Flagler, he thought he could make it happen in five.

He spent more than $30 million of his own money. He hired a crew of about 4,000 African-Americans, Bahamians and European immigrants who never knew how hard they would have to work for $2 a day, a little food and inadequate shelter.

Wading through the mangroves while watching for crocodiles, they put down track in the muck while breathing in smudge-pot smoke that failed to keep mosquito swarms at bay. They suffered heatstroke, snakebite, broken bones and dysentery without decent medical care. Drinking water, readily available only during thunderstorms, was a luxury. Otherwise it arrived by boat or on the slow train coming behind the construction crew.

Some laborers claimed they were being held in bondage. You couldn't blame them. Even if they quit, there was no way to the mainland except by boat, whose captains were in no hurry to transport lily-livered employees back to civilization.

President Theodore Roosevelt, who considered Flagler and Rockefeller "robber barons," had busted Standard Oil into 30 smaller companies to destroy a monopoly in 1906. Roosevelt had no trouble imagining that slavery might be a Flagler business practice. The attorney general was unable to prove a case.

Once the railroad workers crossed the mangrove swamps of the peninsula, they had to contend with miles of open water. Waiting for them in Key Largo, the longest of the keys, were more mosquitoes, sandflies, scorpions, coral snakes, poisonous plants and soft-bottomed bays. Flagler's crew needed 15 months to install track over a 1-mile stretch.

Flagler's civil engineers, all the while, had to invent new technology as they went along. At their disposal were two steamships and an assortment of tugboats, paddle wheelers, dredges, launches and a catamaran. Barges transported concrete mixers, pile drivers and machine shops.

Engineers wondered if the "Seven Mile Bridge," from Marathon to Bahia Honda, might prove impossible to build. Flagler had to import cement from Europe capable of drying underwater. Divers wearing brass helmets, meanwhile, positioned underwater structures. Above them barges swung in the current as workers tried to keep their balance. Everything stopped during the frequent thunderstorms.

Three powerful hurricanes hit the Keys during construction, washing away tracks and hundreds of lives. In a famous story, a worker lashed himself to a tall tree as the storm hit. He avoided drowning, but suffered severe burns from the sap of the poisonous manchineel tree.

So much for working on the railroad.

When the train arrived in Key West at 10:30 a.m. on Jan. 22 it was national news. There were parades and speeches and the unveiling of plaques and photographs taken of Henry Flagler.

That afternoon, the first train departed Key West for Miami carrying passengers who had paid $10.17 a ticket. The trains slowed to 15 mph while crossing the 7-mile bridge, but some passengers shut their eyes in cold fear.

Flagler died after a fall in Palm Beach in 1913. He is buried in St. Augustine.

His railroad, of course, died at sea.

• • •

Hurricane forecasting was primitive in 1935, often a matter of a telegraph office on land receiving a cable from a ship at sea. In the Keys, old-timers watched nature for signs of changing weather; the younger folks kept their eyes on barometers.

Labor Day, Sept. 2, 1935.

The barometer was dropping. There was a hurricane out there somewhere. On Matecumbe Key in the central Keys, folks started to worry. In Miami, railroad officials decided to send a rescue train to evacuate residents on the low-lying island and 800 World War I veterans who were working on a new auto road.

The train was delayed, arriving as the storm hit.

The barometer had fallen to 26.35 — still the lowest reading for any hurricane to hit the United States. The Russell family, an extended clan of 53 brothers, sisters, aunts, uncles and cousins, lived on Matecumbe. They were self-reliant fishermen and lime growers accustomed to harsh weather.

Bernard Russell was 17. His brother Floyd was 8. They and three other siblings and parents were huddled inside a home close to the Atlantic. They fled inland for the sturdier lime-packing house. Shuddering in the wind, the lime-packing house started to come apart. Meanwhile the storm surge — eventually it reached 16 feet — was beginning to flood the island.

Bernard and Floyd's parents had to make a terrible decision: Stay put or grab a small child and run for the railroad bed, the highest point on the island, and hope they might find shelter in a box car.

They made a run for it. Floyd and Bernard never saw their mother alive again. They lost three siblings, too. In fact, they lost 49 relatives in all. Virtually every palm on the island was uprooted or snapped in half. The only thing standing was the locomotive, Engine 447, which weighed 320,000 pounds. The cars were blown off the tracks.

Officially, 408 bodies were recovered, including 259 World War I veterans. Most drowned and some were sandblasted to death. Some were killed by flying debris and a few were impaled on broken tree limbs. Ernest Hemingway, who lived in Key West, arrived in a boat a few days later to see the carnage.

"The railroad embankment was gone and the men who had cowered behind it,'' he wrote. "You could find them face down and face up in the mangroves . . . Then further on you found them high in the trees where the water had swept them.''

In the heat, bodies began to swell and rot. A boat hauled 116 to Miami for burial. The remainder were placed on a funeral pyre and burned on the island.

More than 40 miles of track had vanished. Bridges were damaged or had disappeared.

It was the end of the Eighth Wonder of the World.

The smart set, once again, felt comfortable calling an old man's dream "Flagler's Folly.''

Jeff Klinkenberg can be reached at or (727) 893-8727.

This article has been revised to reflect the following correction: Henry Flagler died after a fall in Palm Beach in 1913. He was buried in St. Augustine.


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