Skip to main content


Following A Train To Sea

May 2024
5min read

Unlike almost everyone there, I didn’t go to the Florida Keys to dive or fish. I went there to follow the path of a railroad that once left the continent and traversed miles of open water and uninhabited tiny islands to reach Key West. The railroad was built between 1904 and 1912 and blew away in a hurricane in 1935. Subsequently its bridges and roadbed were rebuilt into the highway that connects the Keys.

The railroad was the final creation of Henry Morrison Flagler, who sat at the right hand of John D. Rockefeller during the golden age of Standard Oil and used his resulting millions to build up Florida. In 1904 he decided that if he pushed his Florida East Coast Railway down from Miami to Key West, that island’s deep harbor could become the most important port on the Gulf of Mexico. He said at one point, “It is perfectly simple. All you have to do is build one concrete arch and then another, and pretty soon you will find yourself in Key West.” The railroad took the same route that you now take by car.

I set out south from Homestead, below Miami, on U.S. Route 1—the road that replaced the rails. The road cuts straight and flat through scrubby, undeveloped everglades; after twenty miles or so I saw more and more pastel blue water on either side. I knew I was at the start of the Keys when just beyond a short drawbridge I pulled up to the banks of Lake Surprise.

Lake Surprise was the first of many astonishments that greeted the railroad’s builders. The initial surveying party in 1902 discovered a mile-wide inland lake lying across their route at one end of Key Largo. That’s how little known the Keys were. Fifteen months were spent building an embankment through its middle.

Just below Lake Surprise the road turns to head down the length of the Keys. Key Largo didn’t exist until the railroad was built; it was a series of smaller islands that were joined together as part of the construction. On Key Largo in 1990 I passed shopping centers, motels, gift shops, trailer parks, restaurants, and the entrance to John Pennekamp State Park, home of a spectacular living coral reef not far offshore.

I drove on over a short bridge to Plantation Key. At this northern end of the Keys, the old railroad bridges have all been replaced. But farther along, the longest, most spectacular bridges are all still there, though no longer in use. At the end of Plantation Key I stopped at a bridge where the immediate story of the railroad’s death begins. As a hurricane approached on September 2, 1935, a rescue train set out from Miami to try to save hundreds of veterans building an automobile road on Islamorada Key. Delays made the train perilously late, and at one point a loose cable swinging over the track hooked the engine cab and took eighty interminable minutes to work free. By the time the train moved again, winds were gusting close to two hundred miles an hour.

Four miles farther, in the settlement of lslamorada, the engineer couldn’t see the station in the wet and dark and pulled past it as waves washed over the tracks. When he finally found it and the stranded workers started scrambling for the cars, a seventeen-foot wave engulfed the island and pulled the entire train except the engine off the tracks. In the following days the bodies of 288 of the highway workers as well as about 300 residents of the various keys—more than half their population—were recovered. Forty-two miles of filled railroad bed had been washed out, but the steel and concrete bridges all stood.

At the spot where the train had been wrecked I stopped to look at a monolith of coral brick bearing an Art Deco storm scene and inscribed “To the memory of the civilians and war veterans whose lives were lost.” The monument, at about MM 81.5 (mile markers, a tradition begun by the railroad, indicate the distance from Key West), was hard to find. It faces toward Key West and is surrounded by trees on a lawn opposite Islamorada Tackle.

At the end of that key, I reached the first long bridge—Channel Five Bridge, which covers a mile of open water. As with all the longer bridges, the original still stands next to a new highway bridge built to accommodate heavier traffic in the last fifteen years. The old bridge is a low, flat, narrow, concrete-arch structure; next to it the new one soars big and airy. Looking at them— at any of the pairs of new and old bridges—I got a graphic lesson in the progress of structural engineering in our century. The new bridges make it look easy—so easy that they are relatively undramatic.

The Channel Five Bridge leads to Long Key; from the far end of Long Key extends a two-mile-long bridge that was Flagler’s personal favorite. Its 186 reinforced-concrete arches span more than two miles of water like a Roman aqueduct lost in the tropics.

A few short hops between smaller keys brought me from there to Vaca Key, home of the bustling town of Marathon, which began as a camp for the railroad workers. What with the grueling toil, blazing sun, terrible storms, and constant mosquitoes and disease, good laborers were almost impossible to keep. The steadiest supply came from the Lower East Side of New York City, many of them derelicts roped in by promises of a paradise. They lived mostly on houseboats until a 1906 hurricane killed more than a hundred of them in their bunks; after that they mainly inhabited tents on land. Like all the towns in the Keys, Marathon is a stretch of shopping centers, motels, and other low-slung businesses along the main road, but it’s bigger than most.

At the end of Marathon lies little Knight’s Key, whose far end is an especially dramatic place. There the two famous Seven-Mile bridges—Flagler’s and its 1980s replacement—put out to sea. The Seven-Mile was the longest bridge of all, resting on 546 concrete piers in a row plus a long archway beyond that. The trains were allowed a top speed of fifteen miles an hour over water, so they took nearly half an hour just to cross this one bridge and were almost beyond sight of land a good part of the time. It’s easy to see why John Dos Passos called the voyage a “dreamlike journey.” Like all the surviving original bridges, the Seven-Mile is used today mainly by fishermen.

I overheard an elderly couple discuss the span as they strolled out on it. “See, this is the old highway bridge,” the man said.

Long Key Bridge spans open water like a Roman aqueduct lost in the tropics. It’s easy to see why Dos Passos spoke of a “dreamlike journey.”

“Yes, it’s the old railway bridge,” the woman answered.

“No,” he said. “It’s the old highway bridge.”

After the Seven-Mile Bridge a cluster of smaller keys leads to Bahia Honda Key, home to a state park with the best beach on the Keys. I stopped off there not only to put my feet in the water but also to view the old Bahia Honda Bridge, which you can walk out onto at the far end of the park. If the Seven-Mile was the longest bridge, Bahia Honda was the most challenging, for it had to cross the deepest channel. Workers took weeks to find bedrock under the sand. Boxlike steel trusses were built to support the railroad; when the two-lane highway was laid in the late 1930s, there was no way to widen the trusses for it, so it went on top, where it looks and must have felt like a roller coaster.

Bahia Honda was the last big open gap the railroad had to leap. From there on, for the last thirty miles, the keys are bigger and closer together. On Key West there was no available land for a railroad terminal, so Flagler made land—134 acres of it dredged from the Gulf of Mexico. He had the depot designed so the trains could pull up right next to steamships bound for Havana. Today that part of the island is a naval facility closed to the public. Through a big fence I saw a couple of bored-looking sailors and some nondescript industrial buildings.

The next day I got a look around Key West. The main strip, Duval Street, gives the impression that the local economy is based only on T-shirts, postcards, and hangovers, but elsewhere there is plenty to see—not only Hemingway’s house but also hundreds of other beautiful old homes and, among other things, a fine historical museum in a Civil War fort (the East Martello Museum); a museum in the oldest house of all devoted to the town’s former main industry of salvage from sunken ships; and Fort Zachary Taylor, begun in 1845, declared obsolete in 1866, and reactivated for three wars since. Key West is worth a whole article in itself. But don’t look for signs of a railroad there.

—Frederick Allen TO PLAN A TRIP

We hope you enjoy our work.

Please support this magazine of trusted historical writing, now in its 75th year, and the volunteers that sustain it with a donation to American Heritage.