One of the U.S.’s most sought after places to visit and live, Florida is what it is today, in great part, because of three men who had vision and saw the potential. Writer and historian, Rich Grant, tells us about the railroaders who connected the rest of the country to the panhandle state.
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Meet the three railroaders who built Florida
How Florida Transformed from a Swamp in the 1890s into the World’s Largest Tourism Destination
In the 1890s, Florida was the last undeveloped frontier in the continental United States. While railroad tracks raced across the plains, connecting the East with the West Coast and all points in between, Florida was a teeming, uninhabited swamp of unbearable heat, armies of mosquitoes, snakes and alligators, filled with diseases and little medical care. Almost all the population in Florida lived within 50 miles of Georgia.
Miami was an isolated army post of just 300 people. Tampa was not much larger. Palm Beach had one fishing cabin and less than a dozen residents. The pretty palm trees on the beach were not native to the town – it was just a fluke that a ship carrying 30,000 coconuts had sunk off shore, and the nuts had washed on to a deserted beach in the middle of nowhere and taken root.
But this was in the early 1890s. In just a little more than a century, Florida was to become the third most populous state in the United States and the largest tourism destination in the world. How did this happen?
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Much of it happened because of three men. Railroaders. They had all made fortunes in other businesses and came to railroading late in life. But they saw in the wilderness of Florida something that other men had not seen. Henry Flagler was one of the richest men in the world when he became a railroader and he poured $50 million into building railroads and luxurious resort hotels along Florida’s east coast. At the same time, another rich businessmen, Henry Plant saw the same opportunities on the west coast of Florida and almost duplicated the process. And then many years later, Walt Disney looked at central Florida and liked what he saw. Although it might be hard to think of Walt Disney as a “railroader,” his steam locomotives in the Magic Kingdom now carry more passengers a year than Amtrak in Florida. It was Walt’s love of trains that first sparked his idea of an amusement park circled by a train that led to Disneyland, and one of the key elements he envisioned for his new theme park in Florida was a railroad pulled not by a fake locomotive, but by four authentic steam engines.
Though the towns and resorts they built are major cities today, the history behind their development is often lost or forgotten, except in three museums that celebrate these men and what they did. Here are the three men who created Florida and where to learn about them.

St. Augustine became the most elegant resort in the world for a brief time thanks to Flagler.
Meet the Railroaders Who Built Florida
Henry Flagler and the Flagler Museum, Palm Beach
Mark Twain was the one to christen it “the gilded age,” that glorious time of American expansion and opulence that ran from the end of the Civil War to the stock market crash of 1929. No one exemplified the “gilded age” more than Henry M. Flagler. Born in 1830, he made a fortune in salt in the Civil War, went bankrupt, made a second fortune in grain, and established a friendship with another grainy man, John D. Rockefeller. They formed a partnership in 1870 and started a new business called Standard Oil. In a few decades, it was the largest corporation in the world. Wealthy beyond all dreams, Flagler lived in New York, but when his first wife took sick, it was recommended that they go to Florida for the winter, where the warm weather might help her health.
The challenge was, there was no place in Florida that catered to their wealthy lifestyle. So Flagler created one. On their first trip to Florida, Flagler fell in love with the old colonial pirate town of St. Augustine. Flagler was at an age where many men would have retired; instead, he purchased and expanded a railroad and built the first of three hotels in St. Augustine, the Hotel Ponce de Leon.
It was a sensation.
Flagler’s friend, Thomas Edison, installed 4,000 electric lights, making it one of the first electric-lighted buildings in the world, while Louis Comfort Tiffany did the interiors and stained glass windows. At a time where Miami was a wilderness fort, St. Augustine became one of the richest and most elegant resort towns in the world.
The “Achilles heel” of St. Augustine was cold snaps. During one blustery winter it was colder in St. Augustine than it was in New York, and Flagler knew he had to move farther south. He began buying and building railroads. And collecting wives. When his first wife died, he married a second, but she suffered from delusions and had to be institutionalized. He was able to change laws in Florida, obtain a divorce and marry a third.

Henry Flagler statue in front of what is now Flagler College.
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Pushing his railroad farther south, he was granted thousands of acres of land for every mile of track he laid, and eventually his Florida East Coast Railroad stretched for 522 miles, including 128 miles of railroad “across the sea” to Key West. Finished in 1912, the final push of the railroad to Key West was considered the equal to the building of the Panama Canal. It was called the greatest engineering undertaking ever accomplished by one man. Overlooked at the time were many of the means Flagler used to achieve this, including “convict labor.” In this system, African Americans in Florida were arrested on dubious charges such as loitering, and condemned to lengthy prison sentences, where they were “leased out” by the state as cheap laborers, with the state collecting all the revenue. It was a “Jim Crow” era form of slavery that persisted in Florida until 1923.
But there’s no doubt that Florida owed Flagler a lot. He built a string of luxury resorts, established towns and cities along the entire coast, contributed to the construction of streets and churches, opened up huge areas of Florida to agriculture, created Florida’s orange grove industry and changed the worldwide image of state.
As a wedding present to his third wife, Mary Lily Kenan, in 1902, he built Whitehall in Palm Beach, a 75-room mansion that is today open as the Flagler Museum. Palm Beach was always a favorite to Flagler. His 540-room Royal Poinciana Hotel here was the largest wood structure in the world in 1894. The museum is an incredible tribute to the man and to the “gilded age” that produced and supported him.
At the time of its construction, the New York Herald called Whitehall, “more wonderful than any palace in Europe, grander and more magnificent than any other private dwelling in the world.” It could still be described that way. When Flagler died in 1913, his wife sold the home, which was turned into a hotel, but later faced financial problems and was in danger of being torn down.

Entrance to the Flagler Museum and Whitehall.
Of all things, Flagler’s granddaughter, Jean Flagler Matthews, bought it in 1960, and created a nonprofit corporation that has restored the mansion to its original opulence. It is simply incredible to visit. As you walk through the Grand Hall with its painted ceilings, the Music Room with its 1,249-pipe organ, the Grand Ballroom, the site of many costumed balls, the cozy Library with its central fireplace, the intimate Breakfast Room where the Flaglers dined together every day with big windows letting in the Florida sunshine, the large Master Bedroom, and the fun Billiard Room (the only room in the house where Mrs. Flagler allowed spittoons), you get a sense of what wealth was like in this era. But there are plenty of historic photos to also show the outrageous amount of formal clothes they wore, which before air conditioning had to be frightfully warm in Florida.
The highlights for me were the beautiful terrace with wicker chairs overlooking their palm tree garden, the immaculate grounds, and the pavilion that houses Railcar No. 91 – the Flagler’s private railcar in which they traveled back and forth to New York. Don’t miss having a Gilded Age-style tea service lunch in the Cafe des Beaux-Arts, next to the railcar with gorgeous views
From the Flagler Museum there are stellar walks along the shore of Lake Worth. Or stroll a quarter mile to the Breakers Palm Beach Hotel, which is a rebuilt version of Flagler’s hotel, which originally burned down in 1903, was rebuilt in 1904, burned again in 1925, and was finally rebuilt in 1926 into one America’s grandest hotels that still brings the luxury and beauty of the Gilded Age in the 21st century. The hotel is filled with photos and paintings of Flagler and early Florida history.

Lobby of the Breakers Hotel a short walk from the Flagler Museum in Palm Beach.
Henry Plant and the Henry B. Plant Museum, Tampa
Henry Plant was a friend, occasional business partner and sometimes rival of Henry Flagler. While they went on a ten-day cruise together with their wives, they were definitely competitive. The two Henry’s accomplished pretty much the same thing, Flagler on the east coast of Florida, Plant on the west. Henry Plant made his money running an express agency (the early forerunner of Federal Express) during the Civil War and then developed what was called, “the Plant System.” He ran railroads to water terminals where his fleet of steamships would meet them and take products and passengers back and forth to Cuba and all points south among the islands of the Caribbean. Eventually, he owned 1,196-miles of railroads.
Plant may have been at the opening of Flagler’s Ponce de Leon Hotel in St. Augustine in 1888. Regardless, he was aware of it and intrigued. He had small hotels along his railroads, but nothing like the Ponce de Leon. So Henry Plant began construction of his own west coast resort, the $3 million Tampa Bay Hotel, which opened in 1891. The hotel had 511 rooms (Flagler’s had 240), it was five stories high (Flagler’s was four) and it was a quarter mile long! The hotel building alone occupied six acres of a 150 acre resort and had Florida’s first elevator, which still works!
The building itself was a dream. Based on an “Arabian Nights” fantasy of Moorish Revival architecture, it featured six minarets, four cupolas and three domes. The grounds had a racetrack, golf course and a ballpark, where Babe Ruth hit a home run that might have been the longest home run in baseball history. Flagler may have been there for the hotel opening, but he certainly attended his friend Henry Plant’s funeral in Connecticut on June 22, 1899.
Today, the Henry B. Plant Museum occupies half of the former Tampa Bay Hotel. What sets it off from any other museum of its kind is that the current museum is filled with the actual furnishings from its Gilded-age glory. Henry and his wife Margaret Josephine Loughman loved to tour Europe and buy anything within reach. They sent back 40 train car loads of chairs, chandeliers, statues, paintings, lamps and other assorted goods, which all found their way to the hotel, and many of them are still there.
After touring room after room of this huge museum, each loaded with antiquities of every sort, you soon realize that the “gilded age” comes off better on paper than it must have been in real life. The rooms are dark and often gloomy at first glance. But you have to realize that before air conditioning, a dark room would have been a haven from the glaring Florida sun. Especially if you were wearing huge corsets, huge dresses, petticoats, suits and ties.
The other half of the old Tampa Bay Hotel is a student union building for the University of Tampa, which can make it difficult to find and near impossible to park. But it’s worth the effort. There are hundreds of historic items, photos and history here, and you can actually imagine people staying in this hotel, unlike Flagler’s mansion, which just seems a movie set in comparison. Teddy Roosevelt used the hotel as a headquarters during the Spanish American War, and the troops were camped throughout the resort, seven acres of which have been preserved as beautiful Plant Park. You can get to the gorgeous Tampa River Walk here and stroll along the Hillsborough River down to Fort Brooke Park and the Tampa History Center, which has more information on Plant and early Florida.

The Henry B. Plant Museum, today.
Walt Disney Presents Exhibit, Disney’s Hollywood Studios, Orlando
Walt Disney always loved trains. Even when he was becoming the world’s most famous producer of animated films, he kept a Lionel train set in his office. When he discovered one of his employees had a model railroad in his backyard, Walt built one too – a half-mile, one-eighth size train so large that Walt could sit on it and give rides to the kids in the neighborhood. The joy of giving kids a train ride in his backyard gave Walt an idea.
At this time in the early 1950s, amusement parks were trashy, honky-tonk carnivals, usually along the ocean. Walt thought that was a waste – half of the land that could be developed was water! Why not build a theme park for the entire family to enjoy, surrounded by the hotels and restaurants that would support it. Everyone thought he was crazy. But he had a vision for what he called “Mickey Mouse Park.” He said, “I just want it to look like nothing else in the world…and it should be surrounded by a train.”
Disneyland opened on July 17, 1955, in Anaheim, California, and was a phenomenal success. But not to Walt. They had run out of money and had not been able to buy up the land around the theme park, so while Disneyland was spotless, the surrounding area became filled with cheap hotels and attractions.
Walt decide to build another theme park. “I am doing this because I want to do it better,” he said. In November 1963, he flew over the potential site in Orlando and selected it over Tampa or Miami because there was less chance of hurricane damage. A number of dummy corporations were established to begin buying real estate without setting off “land rush” prices. Eventually, they would buy 30,500 acres of land, 48 square miles with some land going as cheap as $100 an acre.
Today, of course, Orlando is the largest tourism destination in the world with a metro population of 2.5 million, more than ten times larger than when Walt first flew over the site in 1963.
For his new theme park, Walt also wanted more emphasis on the railroad. The fanciful Disneyland locomotive had been built from scratch, but for the new park, he wanted real steam locomotives, and after a worldwide search, they found four, beat-up ex-sugar field locomotives in the Yucatan of Mexico. They bought the locomotives for $750. Today (in normal times) the locomotives make 70 trips a day around the 1.5 miles of track, carrying up to 3.7 million passengers – more than any other railroad in Florida and about 10 percent of all the passengers on the entire Amtrak system.

The train station and railroad looping the park was an integral part of Disneyland and then later, here, in the Magic Kingdom of Walt Disney World.
Walt Disney’s amazing story and his love of trains comes to life in a pavilion at Disney’s Hollywood Studios called “Walt Disney Presents.” There’s a 15-minute film and a mixture of artifacts, photos and film clips from life story, which now dates back 100 years to growing up in the small town of Marceline, Missouri, where naturally his first job was working on a train. Though he is a household name, we often forget the genius of Walt Disney, not just in theme parks but in animation, which he revolutionized, and in the growing world of early television, which he also changed forever. Walt said it best himself, “In one way or another, I have always loved trains.” And because of that, Florida – and the world – are happier places.
IF YOU GO: You can hardly step anywhere in Florida without seeing the influences of these three men. Beyond the three museums highlighted, St. Augustine is filled with historic sites related to Flagler, especially the Lightner Museum, which occupies the historic Alcazar Hotel, the 1888 resort hotel Flagler built in the downtown area that now has one of the premier collections of 19th- and early 20th-century fine and decorative art, furnishings, paintings, leaded glass windows, cut and blown glass, and natural history.
The best place to discover Walt Disney is in San Francisco, of all places, at the Walt Disney Family Museum, a wonderful facility in the Presidio that has the locomotive and many of the original cars from his backyard railroad that started it all.
— Story and photos by Rich Grant.
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