The Overseas Railroad: Florida’s “Key” to a Perceived Paradise

Flagler 2

Flagler at Knight’s Key

“Are you sure this railway can be built?” Henry M. Flagler, co-founder of Standard Oil and “Father of Miami,” posed this question to his chief aide, Joseph R. Parrott, in the winter of 1904. With Parrott’s affirmation, Flagler embarked upon an ambitious, unprecedented engineering feat to connect Key West, 130 miles south of Miami, with mainland Florida. The Gilded Age industrialist had already transformed Florida’s east coast into the vacation hotspot it remains today by bringing together its hotel, railroad, and steamship development into a systematic enterprise accessible to tourists. The Overseas Railroad would be his crown jewel—the final feat to fulfill his romantic vision of a revolutionized Florida.

The ocean proved to be every bit the formidable foe that Flagler and his builders suspected as they traversed open water one concrete pier, arch, and rail at a time. Construction began in 1905 in Homestead, Florida, with men facing the immediate difficulties of heat, scarcity of food, water, and supplies, and the incessant assault of insects, which they combated with pyrethrum powder and smudge pots. Three hurricanes (in 1906, 1909, and 1910) collectively claimed over 200 lives of those working on the project. In times of high winds and heavy seas, workers would purposely sink their floating equipment in dredged-out storm channels to prevent it being swept away to sea.

knight's key

Workers stayed in fourteen camps established throughout the keys, including several two-story floating dormitories. During the 1906 hurricane, with winds estimated at 120 miles per hour at Long Key, one of these houseboats broke from its mooring and was swept into the Gulf of Mexico, sending dozens to watery graves. In total, the 1906 storm resulted in 130 deaths, after which Flagler and his team enacted more stringent safety precautions for those at work.


Seven Mile Bridge with temporary trestle

Journeying by train to Marathon in 1909, Florida traveler Winthrop Packard noted from his carriage window that “men cling like birds to slender staging or insecure footholds, swaying to one side to let the train pass, then swaying back again to go to work.” A fellow passenger, whom Packard described as a “lean, knob-muscled navvy,” sat up in great excitement upon seeing his fellow workers. This man, returning from a five-month convalescence in the hospital, was coming back to work after the 1909 hurricane “took his tent from over his head while he was eating his dinner, picked him up bodily, and hurled him against a pile of railroad iron, breaking a leg and other bones.”

On January 22, 1912, seven years after construction began, an elderly but jubilant Henry Flagler rolled into Key West at 10:43 AM, having just completed the maiden voyage across his Florida East Coast Railway extension. Despite his success, we must ask ourselves the obvious: why on earth did he build it? At a cost of $27,127,205, or $212,000 a mile, and with the loss of roughly 200 lives, the consequences seem unpalatable for an extension whose only neighbor for lengthy stretches would be the beating waves of the open ocean. The answer lies behind a deconstruction of our public perception of Key West’s geography. Here too, lies the lasting significance of “Flagler’s Folly,” portions of which were utterly obliterated by the Labor Day Hurricane of 1935.

long key

At the turn of the twentieth century, a number of factors contributed to a vastly different perception of Key West’s importance, economically and geopolitically, than we have today. Far from being “The Last Resort,” Key West was seen as the nexus of an international trading network in the Caribbean and larger Gulf region. Until 1890, Key West remained the most populous city in Florida. Sporting the deepest harbor south of Norfolk, Virginia, it had a thriving maritime economy.

21ffb3c8663f616762cd3c6cac236868_coral20clipart-animated-coral-clipart_408-600Its economy derived from distinctive natural resources. The New York Times, in 1855, noted the important role the reefs played in Key West’s economy: “Everything is coral here, or rather everything is based on coral….” Wreckers, spongers, and turtlers all benefited from the key’s unique maritime environment. A vibrant cigar industry arose as well. Perhaps the biggest enticement for connecting Key West by rail was its perceived geopolitical location. The town’s deepwater port seemed ideally suited to handle increased overseas trade with the Spanish Caribbean, Central, and South America. Moderation of some of the more stringent U.S. tariff policies following the Civil War prefigured increased overseas trade. The opening of the Panama Canal in 1905 poised Key West for its biggest role yet as a commercial entrepot for larger Pacific markets. But these prospects never materialized.dark-purple-coral-reef-hi

Flagler’s overseas railroad had arrived too late to the game. By the time of Key West’s connection by rail in 1912, many of its resources had dried up. Sponges were depleted, turtles were scarce and their soup out of fashion, and Tampa had established itself as “Cigar City.” Alternative modes of shipment came to predominate in coastal cities like New Orleans and Miami. Key West’s quick bid to industrialize proved untenable, as its resources could not keep up with the mass production occurring in expansive, mainland America, and those it did produce were not connected to these larger markets in time to compete. Moreover, the railroad was expensive to maintain and faced constant exposure to storms. Its death knell came courtesy of Mother Nature with the Labor Day Hurricane of 1935.

FEC in storm

When a unit of rescue workers, one of whom was a young Ernest Hemingway, arrived on the scene, they found total destruction and heavy losses of life and property. The forty-plus miles of track between Key Largo and Key Vaca were destroyed. Nineteen miles of track had been swept off its roadbed, with an additional six miles disappearing completely. Later, two of these miles washed up on Cape Sable in the Everglades. In man’s perennial quest to conquer nature, nature had won once again. And yet, much of the Overseas Railroad, with its sound and sturdy construction, had endured. If Flagler’s vision to create a commercial crossroads in Key West had failed, his vision paved the way, quite literally, for Key West’s transformation into:


Flagler’s failure to link Key West economically with mainland America contributed to an image of a land frozen in the past. As author William C. Barnett puts it, Key West made an “economic leap from maritime production past industrialization to tourism and consumption,” creating a vacation destination that feels wholly distinct from the normative landscape of industrial and suburban America to the north. It is this image of the past, frozen in time and exploited to the fullest by tourism boosters that still appeals to visitors today.


The Overseas Highway

Julius Stone of the Federal Emergency Relief Administration recognized the city’s potential when the agency took charge of Key West in July 1934 as part of the New Deal. Stone set forth an ambitious plan to revitalize Key West as a tourist destination. In addition to a massive cleanup, renovation of homes into hotels, and a marketing campaign emphasizing buzzwords like “escape” and “getaway,” Stone realized a shift in public perception of the town’s geography was needed. This meant erasing from history any notion of Key West as a crossroads of a larger maritime network. When a hurricane destroyed an all but defunct railway in 1935, Stone seized upon its remaining infrastructure to reorient the town as a “place apart,” but linked in the dawning age of the automobile.

The State of Florida purchased the roadbed and remaining bridges from the bankrupt Florida East Coast Railway, and set about replacing the railroad with a coastal highway. Construction proceeded rapidly, and the Overseas Highway was opened for use on March 29, 1938. Although the right-of-way was not part of Stone’s original plan to revitalize Key West as a vacation destination, its availability following the 1935 hurricane soon became an essential component. The new highway, built on the foundation of “Flagler’s Folly,” sealed Key West’s fate as “America’s Southernmost City”—a distinctive place, frozen in time and separated geographically from the rest of the world. Rather than view Key West with an international geography—it being just 90 miles from Cuba—we perceive it today as “The Last Resort,” the final terminus on U.S. Route 1, which begins 2,369 miles to the north in Kent, Maine, on the U.S.-Canada border. The Overseas Railroad is a testament to the built environment’s resilience and impact in shaping not only how we engage with the world, but how we perceive it.

Overseas Railroad_1



Alice Hopkins, “The Development of the Overseas Highway,” in Tequesta: The Journal of the Historical Association of Southern Florida, vol. 46 (1986): 48-58.

David L. Willing, “Florida’s Overseas Railroad,” in The Florida Historical Quarterly, vol. 35, no. 4 (1957): 287-302.

Jesus Mendez, “1892—A Year of Crucial Decisions in Florida,” in The Florida Historical Quarterly, vol. 88, no. 1 (Summer 2009): 83-106.

keywest_0.jpg.638x0_q80_crop-smartRoland M. Harper, “Completion of the Railroad across the Florida Keys,” in Bulletin of the American Geographical Society, vol. 44, no. 2 (1912): 90-93.

William C. Barnett, “Inventing the Conch Republic: The Creation of Key West as an Escape from Modern America,” in The Florida Historical Quarterly, vol. 88, no. 2 (Fall 2009): 139-172.



Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s