The railroad that went to sea

Drive south from Miami today and you cross forty-two bridges without thinking much about it. But every one of those crossings exists because of a decision made in 1905 by an aging oil millionaire who had already built most of Florida's east coast and decided, in what should have been his retirement, to do the one thing everybody said was impossible.

Why Key West

Henry Flagler made his fortune as a co-founder of Standard Oil alongside John D. Rockefeller. He came to Florida in his fifties and spent the next three decades building the Florida East Coast Railway down the peninsula, inventing resort towns as he went — Palm Beach, Miami — each one anchored by a grand hotel and reachable by his trains.

The final push had a hard commercial logic behind it. When the United States announced in 1905 that it would build the Panama Canal, Flagler saw the opportunity: Key West was the closest American deepwater port to the canal, positioned to capture Cuban and Latin American trade along with new commerce from the west coast. Key West was also a major coaling station for ships running between South America and New York, and Flagler expected to profit by bringing coal down by rail. The city then held nearly 20,000 people — at the time one of the largest in Florida — sitting 128 miles beyond the end of the peninsula.

The plan was to lay track across open water. Critics named it Flagler's Folly, and the name stuck for years.

Building it

Nothing like this had been attempted by private interests anywhere. Flagler's engineers had to invent methods as they went, and the scale of material moved was staggering — something on the order of 17 million cubic yards placed along the right-of-way.

The work camps strung down the islands were brutal places: heat, mosquitoes in numbers modern visitors cannot imagine, no fresh water except what was shipped in, and hurricane season every single year. Over the seven years of construction, five hurricanes threatened to halt the project and three caused major damage. Men died. Crews quit and were replaced. The work went on.

The most famous stretch is the one you still drive beside today: the seven-mile span connecting Knight's Key with Little Duck Key — the original Seven Mile Bridge, carried on concrete arches and steel spans across open water where the Atlantic meets the Gulf. Pigeon Key, the small island beneath its eastern end, housed the bridge crews and still holds their buildings.

January 22, 1912

The first official train into Key West pulled Flagler's private railcar No. 91, and thousands of well-wishers met him at the station. He was 82 years old and nearly blind. The citizens of Key West presented him with silver medallions made by Tiffany & Co., and his employees gave him a congratulatory telegram rendered in 18-karat gold.

For the first time, you could board a train in New York and ride, unbroken, to an island ninety miles from Cuba. Passengers on the Havana Special crossed miles of open water with nothing visible on either side but ocean. Ferries carried entire railcars on to Havana.

The Keys changed overnight. Islands that had been reachable only by boat suddenly had scheduled service, freight, mail, and visitors. Pineapple and lime growers could ship north. The fishing camps of the Upper Keys became reachable for wealthy sportsmen from the northeast — the seed of the sportfishing industry that defines Islamorada to this day.

The end, in a single night

The commercial case never quite delivered. By the time the extension was finished, ships had extended their range enough that they no longer needed to stop at Key West for coal. The line ran, and it carried people and freight, but it never became the trade artery Flagler had imagined. He died in 1913, sixteen months after riding that first train.

Then, on Labor Day 1935, the most intense hurricane ever recorded to strike the United States came ashore over the Matecumbe Keys. It destroyed 42 miles of track, and the rail link to the mainland was never rebuilt. The full story of that night — including the rescue train that arrived too late — is told here.

Facing the cost of rebuilding, the railroad sold the right-of-way to the State of Florida and Monroe County for $640,000. The bridges Flagler built were converted to carry automobiles, and the Overseas Highway opened in 1938.

Where you can still see it

This is the part most visitors miss entirely. The railroad is still out there, right beside the road:

• The Old Seven Mile Bridge — the original span parallels the modern bridge at Marathon. A restored section is open for walking and cycling out to Pigeon Key.
• Pigeon Key (MM 45) — the workers' village beneath the old bridge, preserved with original buildings and a railroad museum.
• Bahia Honda (MM 37) — the most dramatic remnant anywhere in the Keys. The old rail bridge stands high above the channel with a section removed, and the view from the park below is the one everybody photographs.
• Long Key Viaduct (MM 65) — the graceful arched span that appeared on the railway's own advertising.

In 1979, three of the historic railroad bridges — Long Key Channel, Knight's Key (Seven Mile), and Bahia Honda Channel — were listed on the National Register of Historic Places.

Look for the concrete arches marching away from the highway on either side. Every one was placed by hand, in the heat, by men working a hundred and twenty years ago on the wager of an old man who refused to be told it couldn't be done.