Flagler held a shipping business as part of his personal empire. The canny industrialist realized his railroad needed to reach Key West as the U.S. port closest to the Panama Canal, under construction in roughly the same timeframe as his Over-Sea Railroad.
Building a railroad across more than 100 miles of swamp, thickly wooded islands and, most dauntingly, seemingly unbridgeable miles of open ocean had occurred to Flagler years before, said Jerry Wilkinson, founder and president of the Upper Keys Historical Preservation Society.
Corporate records show Flagler raised the topic at an 1893 board meeting, three years before the Florida East Coast Railway had reached the fledgling community that would become Miami.
“How would he have that vision?” Wilkinson, a Flager re-enactor, still wonders.
Construction began on the Florida East Coast Railway, Key West Extension, in 1905. Seven years and millions of dollars later, Flagler in 1912 rode his own railcar all the way through the Keys (although final construction on the railroad would last several more years).
“The railroad connected the Keys to the mainland for the first time,” Monroe County Library historian Tom Hambright said.
“That probably never would have happened had it not been for Henry Flagler,” Hambright said. “It took his private money to do that. Who else could? No one could come close.”
Key West gave travelers a destination but the Southermost City already was known. It was the third-largest city in Florida in 1905 with a vibrant cigar industry and military installations. “Key West was a boomtown,” Hambright said.
“The railroad opened the Keys to civilization and enterprise,” Wilkinson said. “Eventually the road was going to be built, but Flagler’s railroad got a lot of the work done for the road.
“If nothing else, the raiload probably moved Keys society a step forward by about 20 years,” Wilkinson said. “Where would the water pipeline and electric lines gone, if they couldn’t hang them off Flagler’s bridges?”
Wilkinson speculated that costs of building U.S. 1 without Flagler’s advance work would have made it an expensive drive. “The highway toll would have been much higher and lasted a lot longer.”
Marathon largely evolved as a railroad work camp, later becoming a major freight and passenger port for shipping commerce with Cuba.
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