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The Overseas Railroad (a.k.a. Florida Overseas Railroad and the Overseas Extension) was an extension of the Florida East Coast Railway to Key West, located 128 miles beyond the end of the Florida peninsula. Work on the line started in 1905; the railroad operated from 1912 to 1935.
Flagler was not content to rest by the time his railroad had reached Miami in 1896. The Florida Keys, a string of islands that reach more than 100 miles southwest from the southern tip of mainland Florida, appealed to Flagler. The outermost key, Key West, was only 90 miles from Havana, Cuba. Prior to the 1950s, there was a great deal of freight and passenger traffic between the U.S. and Cuba.; in addition, Key West was closer to the Panama Canal (then under construction) than any other U.S. port. In 1904, Flagler decided to extend his railroad to Key West.
The construction problems were formidable and labor turnover was high. The first portion of the line, from Homestead to Key Largo, was across swamp. The dredging of drainage canals provided material for the roadbed. Along Key Largo, however, the problem was not terrain but insects. Worse than either terrain or insects was the weather: a hurricane in September 1906 destroyed the initial work on the Long Key Viaduct and killed more than 100 laborers. In 1907, the opening of Long Key Viaduct, more than two miles of concrete arches (eventually becoming FEC's trademark), allowed service to begin to where a marine terminal was built.
The 1935 Labor Day Hurricane washed away 40 miles of the Middle Keys section of the line. In addition, the Long Key Fishing Camp was destroyed, along with an FEC rescue train which was — with the exception of steam locomotive 447 — overturned by the storm surge at Islamorada, Florida.
With Flagler gone, the FEC was unwilling to repair a line that had never repaid its construction cost — an unknown figure at the time only hinted at by the federal valuation of $12 million ($200,941,748 today). It was later determined that the total cost of what had been derisively nicknamed "Flagler's Folly" exceeded $50 million ($1,277,592,593 today), all from his personal fortune. The railroad structures, however, were built to withstand the harshest of the Keys' tropical climates. The FEC cut the railroad back to Florida City, 30 miles south of Miami, and sold the remaining land to the state of Florida. As the concrete viaducts and steel trestles survived intact, the state built Overseas Highway (U.S. 1) over them in 1938. Most of U.S. 1 was rebuilt in the 1980s, turning the former viaducts into fishing piers and pedestrian paths part of the Florida Keys Overseas Heritage Trail. The viaducts and bridges were added to the National Register of Historic Places in 1979.
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