History of the Overland Highway to Key West

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Samuel M. McCall

Senior Editor at Wacky Explorer
Sam attended Auburn University and has an MBA in Accounting. He currently lives near Tampa, Florida with his wife, Ashley. They are fans of the Tampa Bay Rays and the Tampa Bay Lightning. During football season you might hear Sam yelling "War Eagle" 'round the house on Saturdays which generally startles the Rotti's. Sam's favorite read, "To Kill A Mockingbird." Favorite movie, "Unforgiven."
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The construction of the overseas railway to Key West was the last major project by developer and entrepreneur Henry Morrison Flagler. Flagler was a founding partner of Standard Oil. He used his fortune and wealth to build a railroad and hotels down the East Coast of Florida beginning in 1885. He built the first railroad bridge over the St. John’s River and by 1894 had extended the railroad to Palm Beach. It was here in Palm Beach that Flagler built a mansion, Whitehall, as a wedding present to his third wife, Mary Lily Kenan.

By 1896, Flagler had extended the railroad to Miami where he established the Royal Palm Hotel. Flagler then set his sights on Key West, the most ambitious of his many projects.

Key West 1912

Key West is the southernmost city in the continental United States. It is approximately 4 miles long and 1.5 miles wide. Later Key West would become home to famed writer Ernest Hemmingway and later, in the 1980’s, would briefly declare it’s independence from the United States. The secessionist’s would quickly surrender a short time later.

The featured picture is of Flagler’s train, with Flagler and his party on-board, departing for Key West for the first time on January 22, 1912. The second picture is a photo of the City of Key West, 1912.

This system of some forty-two bridges connecting Key West to the Florida mainland is one of the longest over-water bridges in the world.

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