A century ago, a journey to the Florida Keys felt like an adventure plucked from the pages of Jules Verne. In January of 1912, the tail end of the Gilded Age, travelers could flee the northeastern winter by heading to New York's Penn Station and purchasing a luxury sleeping compartment on the Havana Special train. Leaving at 10:05 p.m. nightly, the locomotive whistled down the Atlantic coast in a mere 36 hours to balmy Miami, while passengers dined on Floridian seafood and succulent fruit. Around dawn on the second day, the same train continued south for 156 miles into America's most tropical region on the new "Key West Extension"—a single line of rail track that soared above the mangrove swamps and coral specks of the Keys, the wild archipelago that carves a delicate arc through the turquoise shallows for 150 miles south of Miami, between the Atlantic and the Gulf of Mexico. By 10 a.m., it was chugging at 15 miles per hour across the most famous and spectacular of the Extension's 40-plus spans, popularly known as the Seven Mile Bridge. As the name suggests, it crossed seven miles of open ocean, supported by concrete pylons embedded in the golden, shifting sands.

Travelers gazed in awe at the sparkling emerald water through windows on both sides of the carriage. It was as if they were flying: In the shallows some 18 feet below, they might spot dolphins, sharks, turtles or the four-feet-long tarpon prized by game fishermen. The famous writer and Keys fan, John Dos Passos, later called the trip in a letter to his friend Ernest Hemingway, "a dream journey.” And while many travelers stayed in Key West—even before the building of the railway, it was Florida's largest city, a thriving port of 20,000 souls—others would hop directly onto a steamer bound for Havana, Cuba.

Henry Flagler
Developer and railroad magnate Henry Flagler is responsible for much of the development of southern Florida. Bettmann/Getty Images

The brilliantly engineered railway, commonly referred to by contemporaries as "the Eighth Wonder of the World," was the brainchild of one of America's lesser-known robber barons, Henry Flagler. Although less notorious today than titans like Andrew Carnegie or J. P. Morgan, Flagler was once a household name as a co-founder of Standard Oil with John D. Rockefeller. He was one of the world's richest men by the 1880s, but instead of resting on his laurels, he embarked on a risky second career in his mid-50s building railways and luxury hotels in Florida—then the last frontier of U.S. travel—that transformed lonely stretches of sand, including Palm Beach, into thriving metropolises. (His Palm Beach mansion remains as a museum; downtown Miami's 12th Street, where he founded the city's first hotel, is now Flagler Street). His Florida East Coast Railroad Company (FEC) opened up the state to the rest of the U.S. in the 1890s. But Flagler was already 75 years old in 1905 when he approved the wildly ambitious Key West Extension linking Miami to the Keys, a series of coral clumps dismissed by one contemporary writer as "worthless, chaotic fragments... (that) have been aptly called the sweepings and debris which the Creator hurled out to see when he had finished shaping Florida," cites author Les Standiford in his classic account Last Train to Paradise.

For the next seven years, Flagler pumped over $27 million (a then-fantastical sum) into a railway project that many engineers considered impossible. According to Standiford, some thought that he wanted to impress his third wife, Mary Lily Kenan, who was 37 years his junior. Others thought that he was competing with his former partner, John D. Rockefeller, who had by then become more famous. Quite possibly, Standiford suggests, the visionary project was a grasp at immortality. By creating a legacy, Flagler thought his place would be secured in the history books—at the same time (not incidentally) as producing a tidy profit for him along the way. Flagler's larger dream was to turn Key West into a trade gateway to the Panama Canal then being built, bringing U.S. goods to Latin America and returning with cigars, sugar, fish and fruit.

East Coast Railway reaches Miami
When Henry Flagler's Florida East Coast Railway expanded to Miami in 1896, it led to the growth of the city and other resort communities nearby. Bettmann/Getty Images

Then again, Flagler may simply have been driven by the era's desire to conquer nature, like the mountaineer George Mallory, who notoriously explained his own mad (and fatal) passion for summiting Mount Everest in 1923: "Because it's there." The Upper and Middle Keys had only a few fishing settlements, and residents even in the bustling port of Key West traveled just as they had when it was a pirate outpost generations before—by boat.

The magnate proved any naysayers wrong on January 21, 1912, when the first train rolled from Miami into Key West, carrying the jubilant Flagler and his wife in their private luxury carriage complete with a copper roof, elegant dining room and Victorian-style velvet-and-mahogany lounge. Standiford posits that it was as significant a leap forward for U.S. transport as driving the “golden spike” in Utah in 1869 to open the Transcontinental Railroad. Flagler was 82 years old and with failing eyesight when he stepped onto the newly constructed 1,700-foot pier in Key West harbor, built so that passengers could stroll onto the steamers bound for Havana. A crowd of 10,000 greeted him as a hero, with brass bands and local schoolchildren singing his praises. “I can hear the children but I cannot see them,” he confided to his chief of railroad operations, Joseph Parrott. He also whispered: “Now I can die happy. My dream is fulfilled.”

In the Florida Keys, a Century-Old Bridge Reopens as a Tropical High Line
The first train rolled from Miami into Key West on January 21, 1912. Drew Company, Jacksonville, Florida via Wikipedia

And yet, opening with great fanfare three months before the sinking of the Titanic, the train became a similar example of man's hubris. It enjoyed 23 years of operation, including a golden age during Prohibition, when thirsty Americans flocked to Cuba. But on Labor Day weekend, 1935, a Category 5 hurricane smashed into the Middle Keys—still the most powerful storm to ever reach U.S. shores—and the iron rail tracks tossed from their coral beds like strings of spaghetti. More than 400 people were killed in the storm. Even so, Flagler's dream did not so much disappear as metamorphize. The rails were soon paved over for cars, and by 1982 most of the extension’s antique bridges closed and were replaced by modern bridges, which collectively are known as Highway One, the lifeline of the Keys.

Overseas Highway
By 1982, most of the extension’s antique bridges closed and were replaced by modern bridges, which collectively are known as Highway One. Print Collector/Getty Images

Anyone who drives the stretch from Miami to Key West is bound to be mystified by the ghostly remains of the old railway. Rusting bridges loom in eerie grandeur, like a capitalist Stonehenge.

While most of these relics have been off-limits for decades, one 2.2 mile section of the Seven Mile Bridge from Marathon to Pigeon Key, about two thirds of the way along the route at Mile Marker 45, continued to hold a beloved place in the hearts of Key residents. They used it for walking, biking, rollerblading, fishing and sunset-watching, despite its looming dangers. "Old Seven," as it became fondly known, was closed in 2016 for an ambitious $77 million restoration that would have impressed Flagler. On January 12, it reopened as a "linear park"—which seized my imagination as a sort of "tropical High Line," a Floridian answer to the elevated rail-to-trail on Manhattan's West Side located a short distance from my New York apartment, that qualifies as one of America's most pedestrian-friendly historical sites.

In the Florida Keys, a Century-Old Bridge Reopens as a Tropical High Line
Illustration by Emily Lankiewicz

"With the bridge open, the public is able to enjoy one of the most unique marine environments in the whole world," Bernard Spinrad, the president of the community group Friends of Old Seven, told me by email, not long after the ribbon cutting. "The entire community... and the many thousands of visitors to the Keys will benefit enormously from the bridge’s ‘coming back to life’…forever."

A few days after the bridge’s reopening, I decided to see whether I could recapture the Gilded Age travelers' sense of wonder by following the route myself, from Miami to Old Seven and onwards to the end of the line, Key West. I wanted to see how much of the Floridian magic remained.


I started off in the Miami hotel most evocative of the Flagler era, the Biltmore in Coral Gables, where many travelers from the north would stopover for a taste of over-the-top Southern luxury, dining in the Italianate atrium beneath bird-filled palm trees and swimming in what was once America's largest hotel pool, surrounded by ancient Roman statues. It was one of a string of majestic hotels created across the state in the wake of Flagler's railroad projects, which arrived in Miami in 1896 and transformed it from a malarial fishing village to a thriving port and tourist destination. "If it weren't for the train, we could never have established this hotel," said the Biltmore's historian, Candy Kakouris.

Biltmore Hotel in Coral Gables
The Biltmore in Coral Gables, Florida, is one of a string of majestic hotels created across the state in the wake of Flagler's railroad projects. gregobagel/Getty Images

Of the 882 charted Florida Keys—the name comes from the Spanish cayo, meaning “islet”—only 30 are inhabited, mostly those linked by Highway One. The others are tiny outcrops of reef barely above sea level, and poetic clumps of mangrove, quite a contrast from the brash metropolis of Miami, whose beach fronts lined with pastel Art Deco architecture, upscale cafes and swaying palm trees have made it one of America's most popular urban destinations .

About two and half hours after leaving Miami, past the cheesy dolphin parks and strip malls of Key Largo, I pulled in to Marathon, the gateway for Old Seven. The largest settlement on the Middle Keys covers 13 reef-fringed islands, and was named after a rail worker's remark in 1908: "Building this railroad has been a regular marathon." There, the beachfront Isla Bella Resort was decorated with famous prints of Florida birds by the pioneering artist—and regular Keys visitor in the 1830s—John James Audubon. (Despite his love of winged creatures, Audubon liked to shoot his subjects; he sometimes left with thousands of dead birds packed in his luggage to study for his paintings). Early the next morning, I strolled out the hotel front door to a new walkway that runs beneath the modern highway as the access point to the restored bridge.

Stepping onto Old Seven, I was enveloped in sunshine and slapped with fresh salt air. The bridge runs arrow-straight across the water, 16 to 18 feet above the waves, depending on the tides, with freshly paved bike and pedestrian lanes and newly reinforced hand rails. It is more minimalist than New York's beloved High Line, but nature takes up the visual slack with its astonishing palette: the winter skies are a piercing blue, the water below fluorescent green. The ocean horizon sparkling on both sides of the bridge hypnotizes and recaptures the sense of flying through space. Sea birds soar overhead, and at one point I spotted a diamond-shaped stingray drifting across the coral-encrusted shallows. On calmer days, visitors report turtles (five species can be seen in the Keys, including the enormous loggerheads—named after the sailor's mistaken cry when they spotted their shells in the waves, "Log Ahead!") and an array of sharks (lemon, blacktip and nurse). One of the most cherished wildlife sightings is the spotted eagle ray, which can leap from water to reveal a wingspan of nine feet and a whip tail.

Seven Mile Bridge
The renovated Seven Mile Bridge is more minimalist than New York's beloved High Line, but nature takes up the visual slack. Tony Perrottet

The reverie threatened to end abruptly after 2.2 miles at a wire fence: in 1982, a steel swing bridge that opened and closed to allow marine traffic was removed, creating a 253-foot gap and cutting all access to the other 5-odd miles of Old Seven. Instead, a wooden gangway now descends to the Keys' most serene and otherworldly venue: Pigeon Key.


A slice of 1912 lost in the tropics, Pigeon Key was used as a workers' camp during the bridge's construction, with some 400 men based here, most of them recruited in industrial cities of the northeast. Back then, life on Pigeon Island was far from idyllic; as was common in the Gilded Age, laborers were underpaid, overworked and lived in crowded conditions. Earlier in the railway construction project, stories had spread through the U.S. that some of Flagler's men had even tried to flee into the swamps but were caught and used as unpaid convicts, causing such a public outcry in 1907 that a New York court tried to charge his FEC railway company with violating post-Civil War rules banning slave labor. The charges were dropped and Flagler, bristling at accusations of acting like a heartless robber baron, improved conditions, but the six-day work week on the Keys remained grueling.

Workers on Old Seven
Flagler's 3,000 workers were tormented by Florida's summer heat and mosquito plagues, and quit in droves. Courtesy of the Pigeon Key Foundation

The litany of disasters piled up from day one, so much so that the railway was initially referred to as "Flagler's Folly." His 3,000 workers were tormented by Florida's summer heat and mosquito plagues, and quit in droves. Although they managed to dodge the much-feared yellow fever plagues, laborers suffered from dehydration, exhaustion, construction injuries and sometimes rattlesnake bites. Despite early scandals, Flagler by most accounts tried to make life bearable: "Camps are clean," wrote a visiting journalist from the Chicago Tribune, "food good, pure ice and water supplied to each camp, no liquor sold in or near." Head nets were even distributed for the bugs. But nothing could control Florida's elements. Camps along the Key West Extension route were hit by hurricanes three out of seven years, the first drowning at least 125 workers who were bunking in houseboats. Construction costs ballooned as engineers imported steel from Philadelphia, hydraulic concrete from Germany and gravel from Chesapeake Bay. Much of the route was not even properly charted: Surveyors were shocked to find an entire mile-long stretch of water that had never appeared on maps.

Crossing such expanses pushed the limits of technology. The Seven Mile Bridge was the most daunting part of the entire route, described by one contemporary writer cited by Standiford as “a matter of launching a railroad straight at the blank horizon of the Atlantic.” If Flagler was tempted to give up, he never let on. Starting in April 1909, a 32-year old civil engineer named William Krome took on the Herculean task of crossing the expanse (which was actually 6.8 miles).

In the Florida Keys, a Century-Old Bridge Reopens as a Tropical High Line
The work was miraculously completed on the bridge by the end of 1909. Courtesy of the Pigeon Key Foundation

Construction required the round-the-clock work crews based on Pigeon Key to build 746 colossal bridge supports literally in the middle of the ocean. They were in four separate sections due to the varying depths, each one involving different engineering challenges, using barges laden with steam-driven machinery that had to be constantly fed with coal and water, and creating infernal industrial scenes, particularly after dark. After iron pilings were driven down through sand and mud to the bedrock—in some cases, 28 feet below sea level—workers created underwater concrete pedestals assisted by divers in metal helmets with air pumped from above. Iron support spans were then barged one by one from the mainland and secured to the pylons with more concrete, until a "Gibraltar strong" (to use one vivid newspaper term from the time) chain had been created upon which to affix the rail tracks. Despite a hurricane hitting in October, the work was miraculously completed on the bridge by the end of 1909. A total of 25,000 tons of steel had been used.


Today, Pigeon Key’s eight vintage wooden cottages, which are mostly used as offices and classrooms, still cluster beneath swaying palm trees, their porches picked over by ibises and roofs guarded by pelicans.

When I met Kelly McKinnon, one the island's four full-time resident staff and executive director of the Pigeon Key Foundation, the nonprofit that oversees the repair of tropical wear and tear and damage from 2017’s Hurricane Irma, at the foot of the access bridge, he assures me, "It's not always so sleepy here." The reopening of Old Seven in January brought a flood of eager locals from around the Keys who had impatiently awaited the work's completion. The small ribbon-cutting ceremony turned into a Keys party: "People were excited. It was like New Year's Eve." And visitation to the historic islet is going to climb rapidly, McKinnon predicts. Pigeon Key had 216,000 annual visitors when the bridge closed in 2016. The five-acre island played host to everything from concerts to TED talks to fun runs. During its five-year hiatus, only a fraction of that number were able to visit on three daily ferries from Marathon. But in 2022, McKinnon expects numbers to dwarf the old figure. "Old Seven a big economic engine. It brings people from all over the country, it's recognized all over the world. And Pigeon Island is used by the entire Keys community," said McKinnon. Its unique setting strikes old maritime chords. "If you're going to have an event on a tiny island, whatever it might be, it's pretty cool!”

Saving Old Seven was a communal effort. A decade ago, it seemed probable that the bridge would simply be allowed to decay, its walkway too dangerous to traverse. But restoration was pushed by a network of history-loving Key locals in the group SOS ("Save Old Seven"), which morphed into "Friends of Old Seven." The result in 2016 was a creative joint-funding project, with the restoration cost provided by the Florida Department of Transportation, Monroe County and the city of Marathon. Although the bridge's basic structure was intact, it was a painstaking engineering job. Old Seven’s paving had to be mechanically raised by hydraulic jacks in ten-foot sections—a total of roughly 1,100 times—to cut out the original supporting steel girders and replace them with fresh "I-beams" manufactured on site, along with new metal panels and rivets, using a total of 2,586,190 pounds of steel. The bridge joints were repaired, and new decking and aluminum pedestrian handrails were added for the walkway, with three layers of anti-rust paint applied. Surprisingly, given how harsh the environment is, the original concrete pylons, McKinnon said, “only needed a scrape.”


From Pigeon Key, I walked back to Marathon then continued driving the 44 miles south to Mile 0 of U.S. Highway 1, Key West, the end point of American road trips. Today, the former pirate outpost has 25,000 year-round residents, scarcely more than when Flagler arrived. But filled with antique mansions garlanded with tropical foliage, it has one of America’s most energetic party towns. Resisting the happy hour crowds by the pool in the Havana Cabana Hotel, I made the pilgrimage to the Gilded Age version of Mile 0, the waterfront terminus where the celebration for Flagler's first train was held that sunny January morning in 1912. The compact, ornate wooden structure, once part of the last rail station, is painted a tasteful lemon, and nearby is a bronze statue of the elderly rail magnate sitting with a cane on a bench. The station has been converted into a fine "Sail to Rails Museum" recounting Key West's storybook history, but is almost entirely ignored by the crowds heading to the marina's nautical-themed seafood restaurants and yachts offering sunset cruises.

Sails to Rails Museum
The "Sails to Rails Museum" recounts Key West's storybook history. Tony Perrottet

Flagler’s hoped-for explosion of freight traffic never materialized, and even the stream of travelers escaping to Havana during Prohibition could not provide the revenue the Florida East Coast Railroad Company needed. It was already in dire financial straits when, on Labor Day, 1935, winds began accelerating across the Keys. Standiford records that one former resident pithily observed: "We saw pretty quickly that this was going to be a son-of-a-bitch."

Ernest Hemingway, then the most renowned Key West resident—his mansion is today a beloved tourist attraction—secured his fishing boat the Pilar and hunkered down. But as fate would have it, the hurricane landed further north on Matecumbe Key, where residents lived in fragile fishing shacks and some 600 veterans hired as laborers huddled in canvas tents. It escalated to a Category 5 super-storm, with winds of 200 miles per hour—an almost unimaginable force that sent seas surging over the land, reduced visibility to near-zero and turned debris into deadly missiles. As one survivor reported, "I saw bodies with tree stumps smashed through their chests, heads blown off, twisted arms and legs, torn off by flying timber that cut like flying knives." A rescue train arrived for residents but its carriages were knocked over by a deadly 17-foot tidal wave, drowning the passengers and sweeping any who escaped out to sea.

emergency relief train
All but the engine of this emergency relief train was blown from the tracks by the 1935 hurricane, near Islamorada in the South Florida Keys. Bettmann/Getty Images

When the storm eased, Hemingway was one of many who joined the search parties. He carried food to distribute, but found "nothing but dead men to eat the grub." Trees were stripped of leaves, he reported, the earth covered with sand, and dead crayfish and morays. ("The whole bottom of the sea blew over it.") Bodies were recovered from 30 feet up in tree branches. Men were found whose faces were stripped to the bone by blasting sands. Entire buildings had vanished. And Flagler's dream evaporated with them. The railway sold its right-of-way for a paltry $640,000, a fraction of Flagler's investment, and in 1938 the steel tracks were paved over for cars.


On my last night in Key West, I visited the final monument on the trail: Casa Marina, which in 1922 was the last of Flagler's palatial hotels to open its doors. Located on the island's southeastern beach, it is surging with activity, although few of the visitors notice another statue of Flagler in the splendid lobby, or realize that the hotel’s exterior was designed with Spanish arches that echo one of his bridges, the Long Key Viaduct.

I strolled down to the century-old hotel's water sports office—Barefoot Billy's—and signed up for a jet ski tour. Speeding around the turquoise waters, I passed an exhausting array of snorkelers, swimmers, para-gliders, sailors and water-skiers. Throngs were gathered at Mallory Square to watch the stunning sunset, one of Key West's daily tourist rituals.

Floridian nature at its wildest defeated Flagler, but his obsession has allowed the world to enjoy the Keys today. Perhaps that is memorial enough.