Henry Flagler and the Overseas Railroad

HE WAS UNIQUE in the history of the United States. He could have been as rich and as famous as John D. Rockefeller. Instead, Henry Flagler chose to spend the last 30 years of his life building a railroad line in Florida and establishing Florida’s tourist industry. His final triumph, completed only a year before he died in 1913, was the construction of the world’s most ambitious “overseas railroad”—a line stretching all the way from the mainland across the Florida Keys to the southernmost tip of the US, Key West.


For decades before his great Florida adventure, Flagler had been a key partner in the creation of Rockefeller’s gigantic Standard Oil monopoly. According to Flagler’s biographer, David Chandler, Rockefeller readily admitted that Flagler was an inspiration. Indeed, Flagler had contributed more than Rockefeller to the organization of the Standard, and was wholly responsible for the clever legal structure that protected it against antitrust lawsuits. However, Flagler craved an outlet for his colossal creative energies, and that was just what he found in Florida, which he explored in 1883 while on honeyoon with his second wife, Ida.

At the time, Florida was still a young state and was keen to sell its land rights, and Flagler saw that even underdeveloped St. Augustine, the oldest European settlement in the US, was attracting plenty of wealthy tourists. Sensing a golden opportunity, he gave up his daily involvement in the Standard, and set about building a chain of hotels along the east coast—the first of which, the 540-room Ponce de León, opened in St. Augustine in 1888.


Designed by the architects of the Metropolitan Opera and New York Public Library, the Ponce de León was the height of luxury and immediately attracted visitors. However, the local railroads were a deterrent, for they ran on a variety of gauges (see The Track Structure) and so demanded frequent changes of train. What was needed was a reliable railroad that would link the town directly to New York, so Flagler bought up the existing lines and converted them to standard gauge. As he noted: “the average passenger will take a through car ninety five times in a hundred in preference to making a change.” Another problem was that the lines only ran to Daytona, a beach about a third of the way down the coast—beyond that, Flagler would have to lay his own tracks.

Flager’s next port of call was Palm Beach, a natural harbor that he explored in 1893. As always, he inspected the site incognito, to avoid attracting attention, and then returned openly to buy the land he wanted. Within months he opened the 1,100-room Royal Poinciana hotel, which Chandler called “the largest resort hotel in the world… equipped and staffed in the most luxurious manner imaginable,” and extended the railroad south to reach it. The guests did full justice to the luxury of the accommodation, with a hundred private railroad cars arriving each winter for the George Washington Birthday Ball—an event at which the most powerful men in America, including Flagler himself, dressed in the most elaborate drag costumes, complete with fishnet stockings, powdered wigs, and strings of diamonds. Another great draw was an annex called the Breakers, which proved so popular that Flagler turned it into a casino.

To foster local industry, Flagler also established a “Model Land Company,” which, in Chandler’s words, “did more perhaps to actually building up the Florida East Coast than any of his other undertakings.” He encouraged people to plant vegetables, citrus fruit, and pineapples, and when an unprecedented snowstorm wiped out the fledgling industry in the winter of 1884 he secretly spent a fortune helping the affected farmers. He even arranged a link-up with weather forecasters, and if a serious drop in temperature was predicted, his engine drivers sounded six long blasts on their whistles as they thundered through the orange groves, calling on farmers to hurry out with their “smudge pots”—oil-burning heaters that prevented frost from forming on the fruit trees.

Another consequence of these freezes was Flagler’s decision to extend his railroad south, for only 60 miles (100km) away the climate was warmer and better suited to farming. Extending the railroad also entitled him to land grants, and on the basis of these he accumulated over two million acres of territory, including Biscayne Bay, a beautiful spot protected from the Atlantic by a barrier island and watered by the little Miami River. At the time, the area was “mostly swamp, and was filled with mosquitoes, snakes, mangrove thickets and Spanish Bayonet” (a nasty type of cactus), but Flagler tamed it and brought water and electricity to the town he established there. The locals wanted to call the town “Flagler,” but Flagler declined the honor, preferring to name it after the river. Thus Miami was born. The following year he set about building another luxury hotel, the Royal Palm, which was as popular as the Royal Poinciana. The railroad arrived at Miami in 1896, completing a 500-mile (800-km) line that ran south from the neighboring state of Georgia through Jacksonville and the resorts Flagler had built. Anyone glancing at a map could see that Miami was the end of the line, but Flagler kept on going, out to sea, away from the mainland and over the Florida Keys—an archipelago that sweeps southwest from Miami to Key West, far out in the Gulf of Mexico. “There is an impelling force within me,” he told a friend, “and I must carry out my plans”—and the result was his 128-mile (206-km) “overseas railway.”

In one respect Flagler was lucky. By the time his plans were ready, President Theodore Roosevelt had authorized the construction of the Panama Canal, making Key West a potentially vital transportation hub. As for getting the work done, Flagler simply found the right man for the job and left him to it, ignoring the question of cost, even though there were no more grants to be had. His chosen engineer was Joseph Carroll Meredith, who had already built the massive docks at Tampico on the Gulf of Mexico. However, before he got started on the offshore part of the route, Meredith had to lay 91 miles (146km) of railroad through the Everglades, an ordeal in which every kind of danger and annoyance was encountered, from apparently bottomless swamps and uncharted lakes to snakes, alligators, mosquitoes, and obstacles that only the biggest dredgers in the country could move. Then he faced the 37 miles (60km) of the “overseas” railroad itself, a route demanding 17 miles (27km) of bridges and 20 miles (32km) of embankments—a feat of engineering that has never been equaled. The Long Key viaduct alone measured 2½ miles (4km), and was second only to the 7-mile (11-km) Knights Key viaduct, which rested on 366 concrete columns and had a swing bridge to allow ships to pass through it. Without dry land for accommodation, the 4,000 workers were housed on enormous barges, which contained all the facilities needed for survival, including vast quantities of fresh water. However, there was still a high casualty rate, both from accidents and disease, and a hospital was built in Miami to treat the afflicted. The elements also caused havoc, not least in 1906, when a hurricane sank an accommodation barge, causing at least at least 70 deaths, and delaying construction for a year.


The whole Florida East Coast Railway project was completed at a cost of $20 million ($500 million in today’s money) and in less than seven years. This was largely thanks to the loyalty of Flagler’s men, one of whom told a reporter “there isn’t one of us who wouldn’t give a year of his life to have Mr. Flagler see the work completed.” And see it he did, opening the line to the public on January 22, 1912, tearfully exclaiming: “my dream is fulfilled, now I can die happy.” He had never expected to see the project completed, predicting 20 years earlier that it would take 30 years to finish, and accurately forecasting: “I have only 20 more years to live.” The line’s completion was celebrated by the introduction of the Havana Express, a regular through service that arrived at Key West only 52 hours after leaving New York, giving passengers the luxury of strolling across the quay to take a ship to Cuba, a mere 90 miles (45km) away. Flagler, his life’s work accomplished, died a happy man the following year.

Sadly, however, the line never prospered. It failed to attract many passengers, and proved to be unreliable since it was affected by bad weather. Consequently, the railroad went bankrupt in 1932, and the offshore track was destroyed on Labor Day 1935, during the worst storm of the century. Nevertheless, Meredith had built his railroad well. Highway 1, which replaced it, was constructed on the roadbed that Flagler had financed. Indeed, Florida, the Sunshine State, has much to thank him for. When he started work it was one of the poorest states in the Union—today it has one of the strongest economies in the world.

If you find an error please notify us in the comments. Thank you!