The dream of one man changed the isolation of the Florida Keys for all time. Native New Yorker Henry Flagler, born in 1830 and educated only to the 8th grade, established the Standard Oil Company with John D. Rockefeller in 1870 and became a wealthy, well-respected businessman. In 1885 he purchased a short-line railroad between Jacksonville and St. Augustine and began extending the rails southward toward Miami, then only a small settlement.

Henry M. Flagler

Flagler's vision of his railroad project went beyond Miami, however. He wanted to connect the mainland with the deep port of Key West, a booming city of more than 10,000 people, in anticipation of the growing shipping commerce he thought would be generated by the opening of the Panama Canal in the early years of the 20th century. He may even have set his sights on eventually connecting Key West with Cuba.

The railroad extended to Homestead, at the gateway to the Keys, by 1904. The year 1905 saw the commencement of what many perceived as an old man's folly: a railroad constructed across 128 miles of rock islands and open water, under the most non-idyllic conditions imaginable, by men and materials that had to be imported from all over the world. Steamships brought fabricated steel from Pennsylvania; cement from Germany and Belgium for use as concrete supports below the water line; cement from New York state for above-water concrete; sand and gravel from the Chesapeake; crushed rock from the Hudson Valley; timbers and pilings from Florida and Georgia; and provisions from Chicago. Barges carried fresh water from Miami to the construction sites. Nothing was indigenous to the Keys except the mosquitoes and the sand flies.

Chief Engineer William Krome

By 1908 the first segment, from Homestead to Marathon, was completed, and Marathon became a boom-town. Ships brought their cargoes of Cuban pineapples and limes here, where they were loaded onto railway cars and sent north. (The railroad turnaround was at the present site of Knight's Key campground.) Railroad workers used Pigeon Key (see our Attractions chapter) as a base for further railway construction.

The 7-mile "water gap" between Marathon and Bahia Honda took some engineering prowess to overcome, and the completion of the project was severely hampered by several devastating hurricanes in 1909 and 1910. But on January 22, 1912, Henry Flagler, by then age 82, finally rode his dream from Homestead to Key West, across 42 stretches of sea, over 17 miles of concrete viaducts and concrete-and-steel bridges, over 20 miles of filled causeways and ultimately traversing 128 miles from island to island to the fruition of his vision. He entered Key West that day a hero. He died the following year probably never knowing that his flight of fancy changed the course of the Florida Keys forever.

Flagler in Key West

Flagler's railroad, called the Key West Extension, made Key West America's largest deepwater port on the Atlantic Coast south of Norfolk, Virginia. Trade with the Caribbean increased, and Key West flourished for 23 years, recovering from the loss of the sponge and cigar industries.

The railroad stop on Key Largo was called Tavernier and developed into a trading center for the Upper Keys. Pineapple farming faltered in Key Largo and Plantation Key from a combination of tapping out the nourishment in the thin soil and market competition from the shiploads of Cuban pineapples transported by railway car from the docks of Key West to the mainland. The railroad company built a fishing camp on Long Key that attracted sportfishing aficionados from all over, including camp regular, writer Zane Grey. Real estate boomed for a time, as people came to the Keys to homestead. The Florida East Coast Railroad Company completed construction of Key West's first official tourist hotel, the Casa Marina, in 1921. La Concha was built in 1928.

In 1923 Monroe County appropriated funds to construct a road paralleling the railroad. The bumpy rock road crossed Card Sound with a long area of fill and a wooden bridge. Half a dozen humpback bridges crossed the creeks and cuts on Key Largo. Extending the length of Key Largo, the road continued over Plantation Key, Windley Key and Upper Matecumbe. At the southern end of our island chain, a 32-mile narrow road connected Key West with No Name Key off Big Pine Key. A car ferry service provided the waterway link between the two sections of roadway, which traversed what we now call the Upper and Lower Keys.

Still, the journey across this 128-mile stretch from Homestead to Key West proved a rugged, dusty, insect-ridden, costly, all-day affair, and tourism did not flourish as hoped and expected. Fresh water remained a coveted, scarce resource in the Florida Keys. Cisterns saved the funneled rainwater, which was parsimoniously meted out. Salt water was used whenever possible, and wash days were also always bath days. Hardly a tourist mecca, this.

The Great Depression delivered a near-fatal blow to the Florida Keys with a one-two punch. The cigar industry had moved to Tampa, sponging went to Tarpon Springs and lighthouses had put an end to wrecking long before. The population of Key West dropped from 22,000 to 12,000. By 1934, 80 percent of the city's residents relied on government assistance. The Federal Emergency Relief Administration stepped in and commenced development and promotion of Key West as a magnet for increased tourism in the Keys.

To that end, developers began building bridges to connect the watery cavities between the Middle Keys to each other and to the two sections of finished roadway. A "bonus army" of World War I veterans was employed to accomplish this momentous task. However, in 1935 Mother Nature reasserted her authority and once again charted the destiny of our islands. On Labor Day, what today we would call a Category Five hurricane hit the Upper and Middle Keys, destroying much of Flagler's Railroad. Hundreds of lives were lost when the 17-foot storm surge hit the bridge-building crew working on a bridge at Islamorada.


Because of mismanagement and lack of foreign freight heading northward from Cuban and Caribbean ports, the railroad was already in receivership. The railroad chose not to rebuild, citing financial difficulties. It had by this time become cheaper to haul cargo by truck than by train. The county's Overseas Road and Toll Commission purchased the right of way from the Florida East Coast Railroad and converted the single track railway trestles, which remained intact after the hurricane, into two-lane bridges for automobiles. The highway from Homestead to Key West opened for traffic in 1938.

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