In the early 20th century, Henry Morrison Flagler, a business partner of John D. Rockefeller, had already made a ton of wealth and recognition through financing the development of Florida’s untamed and distant east coast. His new aspiration was to build a railroad between the remote city of Key West and mainland Florida. While many deemed the project outright insane, Flagler defied expectations and turned his vision into reality. The railway stood as a remarkable accomplishment for over 22 years, regarded as the most ambitious engineering marvel of its time. Referred to as “Flagler’s Folly,” the railroad gained widespread attention and, upon its completion, was often celebrated as the 8th Wonder of the World, a title it held until its unfortunate destruction in 1935 due to the devastating impact of one of the century’s deadliest hurricanes. Fancy to hear the full story and see some pictures?
In the late 1800s, St. Augustine, Florida, marked the end of what was considered “civilization,” while South Florida was nothing but swamps with alligators, mosquitoes, and palm trees.
Flagler, who had successfully consolidated railways in northern Florida with the southern terminus in Jacksonville, FL saw an opportunity to further expand his railway southward. In doing so, he essentially “opened” to America and the world what is now known as Florida, famous as a premier vacation destination.
However, to build a railroad, people needed a place to stay, so he hurried to build the Hotel Royal Poinciana in Palm Beach, FL. At the time, it was the largest wooden building in the world, with 300 rooms. This hotel didn’t last long as wood simply doesn’t survive in this harsh unforgiving climate.
Flagler didn’t relent and built a new hotel called the Breakers. What people know today as the Breakers is actually the third hotel built on this place. It was completed in 1929 using new building materials - concrete over iron cast. This proved to be a very durable combination of materials.
As anticipated by Flagler, people came to Southern Florida and found great enjoyment in the area. His owning both the transportation and hospitality businesses even further enriched him.
Julia Tuttle, a charismatic businesswoman from what is now Miami, asked Flagler to extend his railway to Fort Dallas, the future site of Miami. He declined, saying that he’s pretty happy with his very successful business in Palm Beach. What came next taught him a tough lesson. A particularly cold winter, which, despite the common belief, occasionally occurs in Florida, led to the freezing of all oranges as far south as Palm Beach. Surprisingly, Miami, located 60 miles south of Palm Beach and blessed with a tropical climate, remained unaffected. When Julia Tuttle presented Flagler with a basket of unfrozen oranges from Miami, he had no further hesitation to extend his railway down there.
The introduction of the railway in Miami fuelled a significant surge in growth, leading to unprecedented prosperity. The city even suggested changing its name from Miami to Flagler, but it seems Flagler, in all likelihood due to his humility, declined the honour.
A big visionary, Flagler, already well aware of the construction of the Panama Canal, saw another opportunity to extend his railway to Key West, often referred to as America’s Gibraltar. This strategic location had a deep-sea port, allowing ships from Asia to dock, with Flagler’s trains carrying cargo to various parts of America.
However, the challenge was how to build a railroad over the ocean. Even today, it puzzles me how people could dare to do something like this 100-150 years ago given the modest engineering advancements of the time.
The work required was a huge battle of human resilience against powerful natural forces. Many workers enlisted in exchange for receiving housing, three meals a day, and a daily wage of $1.25. The everyday challenges, such as brutal heat and hungry mosquitoes, became unbearable for some, while hurricanes posed fatal threats. The workers faced a constant struggle to get enough food, water, and medicine for survival. The book titled “Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of the Railroad that Crossed an Ocean” by Les Standiford recounts the stories of the railroad’s construction.
It’s fair to say that it was the regular people working on the construction who brought Henry Flagler’s vision to life. I visited Flagler’s home turned museum in Palm Beach and it just amazes me how much wealth this person possessed while people were literally dying for $1.25 a day. It’s wild capitalism, no doubt.
The Over the Sea Railway would eventually be 126 miles / 202 km long, built over open ocean and using the Florida Key islands as stepping stones. The construction of the Bahia Honda Bridge from 1909 to 1912 proved to be one of the most challenging segments, primarily due to the presence of deep channels. It posed numerous challenges for both workers and engineers. The channel, reportedly exceeding 30 ft / 10 m in depth, marked the greatest underwater depth encountered along the entire route. The railroad bridge was exceptionally narrow. Before traversing the truss bridge, the train conductor would caution passengers, advising them to keep their heads and arms inside the train car.
People worked in shifts, as short as 45 minutes due to tides and currents. The work continued till the night before the opening on January 22, 1912, when Flagler rode his famous car No 91 from Palm Beach to Key West.
Sadly, in 1935, the Labor Day Hurricane wiped out 40 miles / 64 km of the Over-Sea Railroad’s tracks in the upper Keys, pushing the already financially strained Florida East Coast Railroad to the brink of bankruptcy. Unable to afford reconstruction, the state of Florida acquired the remaining railroad components, repurposing them for the foundation of the Overseas Highway which is still in use today.
The Labor Day hurricane’s true toll extended beyond the loss of tracks. Over 250 World War I veterans tragically lost their lives. This historic hurricane remains one of the strongest ever recorded, leaving a tragic story of destruction and human sacrifice.
The Florida East Coast Railway still exists to this day and owns 351 miles / 565 km of tracks from Jacksonville to Miami. According to their website, the company is the exclusive rail provider for Port Miami, Port Everglades and Port of Palm Beach. It provides freight train service as well as leases its tracks to the private commercial train operator Brightline. Interestingly enough, although not affiliated, Brightline draws parallels between Flagler’s railroad legacy and their modern high-speed train service linking Miami and Orlando. They have a nice wall exhibit at the Miami Station ∎.
This was really interesting. I had no idea there was once a railroad to Key West.
What I appreciate the most about this piece is your ability to focus on the few things that really matter. Summarized very nicely. Thank you.