Henry Flagler is a name that will be instantly familiar to Florida history enthusiasts, and his influence is still apparent throughout the state. One of Flagler’s many projects in Florida was the development of the railroad system which tied in to his interest in promoting and popularizing Florida as a tourist destination. One of his most ambitious projects, the construction of a railway to the Florida Keys, called “Flagler’s Folly” by his critics, is the subject we’ll look at today.

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Daytona daily news-January 14, 1905

Flagler’s involvement in railroad building in Florida stretches back to the 1880s. By the early 20th century, Flagler was of the opinion that a railway needed to reach the Florida Keys. The “excitement generated by” U.S. acquisition of and future “construction of the Panama Canal in 1902 made him anxious to develop a port” in the southernmost area of Florida (Stronge 52). Flagler knew reaching a port in Key West would be difficult given its remote location, and decided to remedy this by expanding his extant railroad line further south. While his expansion opened before the canal that inspired its construction, it nonetheless took seven years for the Florida East Coast Railway to complete the 120+ mile project. In that time, many, including the Florida press, questioned the decision to build in an area “destitute of soil” that required materials to be imported to build above the tideline.

Building this particular segment of railroad was not a straightforward venture for Flagler. In addition to being an engineering challenge, construction itself was plagued by a “chronic labor shortage in the state” as well as catastrophic weather events (Akin 215). Hiring a labor force largely from outside of Florida, Flagler‘s railroad faced accusations of peonage which went to trial in 1908 (a charge the Ocala evening star reported as false) and were eventually dismissed. The construction timeline and plans were also altered several times due to the damage sustained by hurricanes in 1906, 1909, and 1910. Delays became a newsworthy topic in papers that sporadically provided updates on the project. After the 1909 hurricane, a reprint of a Miami Metropolis story in the Pensacola journal announced a “setback of a year.” Despite this, the reporter editorialized “nothing short of total destruction of the line would deter Mr. Flagler from executing his plan.” While hurricane damage proved a setback, it also served as a learning opportunity. According to scholar Edward Akin, the destruction caused by the 1910 hurricane served as a “valuable lesson” for Flagler regarding which materials were capable of withstanding heavy winds and rain (Akin 221).

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Pensacola journal-October 31, 1909

The railway finally opened, with much fanfare, on January 22, 1912. Those in attendance included Flagler as well as “a large delegation of United States congressmen and senators” along with “military personal, foreign ambassadors, and Florida officials” (Akin 223). In a proclamation promoting the extension’s impending opening, Governor Gilchrist claimed the project to be “of nation-wide and of world-wide importance, being second in importance only to the construction of the Panama canal (sic).” Another article in the Pensacola journal reported that those referring to the project as “’Flagler’s folly’ now admit that it was a piece of far-sighted business sagacity.” Henry Flagler passed away May 20, 1913, and the construction of the “Over-Sea” road served as an example of his substantial impact on the state. Unfortunately, the Key West Extension is viewed as a business failure having “never earned the expected revenue before the Labor Day hurricane of 1935 destroyed it” (Akin 223). In some ways however, the memory of Flagler’s railroad lives on. The route and some of the original railroad structure, which opened in 1938, now comprise the Oversees Highway as part of U.S. Route 1.

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Pensacola journal-January 30, 1912

Citations and Additional Resources

Akin, Edward N. Flagler: Rockefeller Partner and Florida Baron. Kent, Ohio: Kent State University Press, 1988.

Stronge, William B. The Sunshine Economy: An Economic History of Florida since the Civil War. Gainesville, Florida: University Press of Florida, 2008.

“The U.S. Finishes a $57,000,000 Overseas Highway to Key West.” LIFE, April 25, 1938. https://books.google.com/books?id=5koEAAAAMBAJ&printsec=frontcover&source=gbs_ge_summary_r&cad=0#v=onepage&q&f=false.

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