Linking the Keys

On January 22, 1912, the nearly twenty thousand residents of the city of Key West, Florida, located on a small island some 128 miles south of the Florida peninsula, observed the completion of an overseas rail connection to the mainland. The Florida East Coast RailwayExternal served the island until 1935, when it was destroyed by a hurricane. It was replaced in 1938 by the Overseas Highway, built on the foundation of the old railroad bed. This system of forty-two bridges, which connects the Florida Keys to the mainland, is one of the longest over-water roads in the world.

Mr. H. M. Flagler and Party Leaving First Train to Arrive at Key West, Fla. Oversea Florida East Coast R.R. Harris Co., c1912. Panoramic Photographs. Prints & Photographs Division

The construction of the overseas railway linking the Florida Keys to the mainland was the last major project undertaken by pioneering Florida developer Henry Morrison FlaglerExternal. After losing $100,000 in the failure of his first business venture, Flagler earned his fortune as a founding partner of Standard Oil. He visited St. Augustine in 1883 and, realizing the potential for the development of improved hotels and transportation, began construction in 1885 of the 540-room Hotel Ponce de Leon. Flagler then bought and upgraded the Jacksonville, St. Augustine & Halifax Railway, built a railroad bridge across the St. John’s River, and by 1894 had extended the railroad to Palm Beach, where he developed two large hotels: the Hotel Royal Poinciana and the Palm Beach Inn, later renamed The Breakers. Flagler’s mansion, Whitehall, a wedding gift to his third wife, Mary Lily Kenan, was constructed in Palm Beach in 1902.

Key West, Fla. from City Hall Tower. Harris Co., c1912. Panoramic Photographs. Prints & Photographs Division

In 1896, Flagler extended his railway to the area that was soon named Miami. His investments in the town included the Royal Palm Hotel, opened in 1897. Henry Flagler died in 1913, a year after the completion of his renamed Florida East Coast Railway to its southern terminus in Key West.

Key West, the southernmost city of the continental United States, is a sand-and-coral island approximately 4 miles long and 1.5 miles wide. American businessman John Simonton acquired the island from a Spanish army officer in 1822; by 1823, the U.S. government officially recognized it as a part of the United States.

Drew’s New Map of the State of Florida, Showing the Townships… up to the Year 1874. Columbus Drew, creator; Jacksonville, c1873. Railroad Maps, 1828 to 1900. Geography & Map Division

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