The Historic Charm of Key West

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On this date in 1912, many of the 20,000 residents of Key West welcomed the first train that chugged into their city. Aboard it, in the best car, was the man who dreamt up the railroad and financed it: 82-year-old Henry Morrison Flagler.

Having made his fortune co-founding Standard Oil with John D. Rockefeller and Samuel Andrews, Flagler foresaw limitless possibilities in Florida during his first visit in 1878. He loved the weather, but lamented the lack of rail transportation, and of first-rate hotels. And so he began his personal project: He started in Jacksonville, laying tracks from one city to the other, and constructing or building first-rate hotels in each place along the way.

When Flagler got to Biscayne Bay in 1896, the locals in that little settlement -- there were only 344 registered voters -- wanted to name the town after him. He declined the honor, deferring to the Indian name of the river that bisected the settlement: Miami.

As was his habit, Flagler also built some posh lodgings in the new city; namely, the five-story Royal Palm Hotel, complete with 400 rooms, a rotunda, and a 578-foot long veranda.

“In essence,” notes the Flagler Museum in Palm Beach, “Henry Flagler invented modern Florida. But he wasn’t done: next Flagler turned his gaze to the water, specifically to the Florida Keys. 

Could a railroad be built over the ocean, connecting the string of Florida’s “key” islands all the way to Key West, some 128 miles away? Henry Flagler’s answer to such questions was always “When can we get started?” Construction of the Over-Sea Railroad line commenced in 1905.

The project took seven years and employed some 4,000 men. In what probably should have been seen as a harbinger, work was stopped by five hurricanes, three of which did major damage. But finally it was finished and at 10:43 a.m. on January 22, 1912 a train that had originated in New York rolled into the newly constructed train depot in Key West with Henry Flagler and his third wife as passengers. A portion of that station still stands, along with a small museum, at the Historic Key West Seaport at the corners of Margaret and Caroline Streets.

Henry Flagler died the following year and a 1935 hurricane took out his Over-Sea Railroad. A highway was built on the pilings, and it still stands. Visitors to Key West today can arrive by car, or cruise ship, or at the small local airport famous for its delightful sign, “Welcome to the Conch Republic.”

The tourists, most especially those who come on the cruise ships, have been good for business but bad for historic ambience. But Key West retains its charm if you know where to look -- and when.

The island is best explored on foot or bicycle early in the morning. Roosters crow as you make your way in the dawn’s light from your hotel through the Truman Annex which houses the Truman Little White House, where the 33rd president of the United States came for relaxation. It’s the only such presidential site in Florida, and it’s worth visiting. (In February and March, the museum is putting on a show, “I Like Ike: Songs of the Eisenhower Era.” I can’t help but wonder what “Little Harry” would have thought of that.)

Continuing into the old part of the city, we get to Whitehead Street, and pass Ernest Hemingway’s old house. This is some museum. Privately owned, and run on a shoe-string it manages to keep Papa’s spirit alive. It opens at 9 a.m. 365 days a year, which is fitting, because a writer never knows when inspiration will be needed.

After stopping at Blue Heaven for breakfast, we get turned around -- the “we” in that sentence is me and Ethics and Public Policy Center vice president Michael Cromartie -- and find ourselves riding our bikes through a cemetery. There we come across a large gravesite; many of the sailors aboard the USS Maine are buried there.

We pick a few wild flowers, put them on the graves, doff our caps, and ride away quietly. I’m “remembering the Maine” today because this morning Cromartie went to the hospital for cancer treatment. Michael is a man of faith, so prayers are welcome. 

Carl M. Cannon is the Washington Bureau Chief for RealClearPolitics. Reach him on Twitter @CarlCannon.

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