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Overseas Highway

The Florida Keys’ Famous Overseas Highway — The Historyof US 1 and Why It’s a Road

There aren’t too many tropical island paradises that you can drive to. Thanks to the historic asphalt lanes called the Overseas Highway, only Key West can claim such a title. US 1, or “Useless One,” as the locals have been known to say, connects our lovely island with the rest of America. In fact, you can follow Route 1 all the way north, through Miami, Washington DC, New York City, and all the way to Fort Kent, Maine, where you can cross the border into Canada. 

But while the rest of US 1 has plenty of history and interesting tidbits, the Florida Keys section is really interesting. 

Henry Flaglers Overseas Highway to Key West

Henry Flagler and the Overseas Railroad

The dream of connecting Key West to the mainland became a reality long before highways were the transportation mode of choice. Railroad tycoon Henry Flagler is the local legend who made it happen, the man who made the Overseas Railroad a reality. 

Flagler made his money as a co-founder of Standard Oil along with John D. Rockafeller. He became interested in Florida while trying to find a warmer winter climate for his first wife. His interest continued as he built a series of railroads leading to expensive resort hotels (also built and owned by Flagler). Many of Florida’s big east coast hotspots were, more or less, put on the map by Flagler: St. Augustine, Ormond Beach, Daytona Beach, Palm Beach, and Miami. His rail network became known as the Florida East Coast Railway or FEC. 

However, the idea of linking Key West to the railroad was not entirely for the benefit of snowbirds and tourists. Around 1905, the Panama Canal was just opening. Key West was the nation’s closest deep-water port to the canal, so connecting it by rail to the rest of the country could have been huge. At least, that was the thinking at the time.

But, as simple as it all sounded, it turned out to be quite a hassle for Flagler. Different routes to Key West were explored, including one that bisected the Everglades and crossed 27 miles of open water. That plan got scrapped, and it was decided that building 47 different bridges and linking the Florida Keys together would be easier. 

Building the railroad was a national spectacle covered in the press. Many called the project “Flaglers Folly” for all the hardships encountered. At one point, more than 4,000 workers were employed to build all the bridges, viaducts, and filled-in islands necessary to complete the route. Summers brought hordes of mosquitoes and outbreaks of tropical diseases. And then there were the hurricanes: major storms in 1906, 1909, and 1910 all threatened to derail the railroad before it even got completed.

But Flagler prevailed, and in 1912, he rode his private railcar on the first train to arrive in Key West. He had proved his naysayers wrong, and his achievement was branded the “Eigth Wonder of the World.”


Unfortunately, Flagler’s railroad didn’t last long. Freight business from the Panama Canal never materialized—the ships simply bypassed Key West and docked nearer their destinations. 

But the final nail in the Overseas Railroad’s coffin was the Great Labor Day Hurricane of 1935. It was one of the worst storms on record to this day. The Category 5 storm made landfall in Islamorada with 185 mph winds and a pressure of 892 millibars (still the lowest barometer reading ever recorded in the US). The storm washed out most of the bridges and fill from the railroad, and caused more than 400 deaths. There’s a memorial to the hurricane and those who perished in Islamorada. 

The railroad company was already bankrupt before the storm, so they had no way to rebuild. The right-of-way was sold to the State of Florida. 

If you’d like to learn more about the building of the historic Overseas Railroad, check out Les Standiford’s fantastic book Last Train to Paradise. 

Photo Provided by: U.S. National Archives and Records Administration

US Highway 1 — America's Main Street

While Flagler was dreaming of rail travel, the rest of America became enamored with the automobile. Flagler probably didn’t mind the fact, however, since he made his real money in oil.

Around 1911, an auto trail known as the Quebec-Miami International Highway was established. In 1915, it was renamed the Atlantic Highway, with a new northern limit in Calais, Maine. Portions of the route in New England began to be known as Route 1—a name that stuck. 

Through various state, federal, and special interest groups’ efforts, the US adopted a numbered highway system in the mid-to-late 1920s. Using existing state and county roads, the idea was to connect existing segments into longer routes that could easily be used for interstate travel. North-south routes were numbered from east to west, so Highway 1 is basically the first north-south highway on the East Coast. 

Before the 1935 Labor Day Hurricane, US 1 ended in downtown Miami. When the hurricane destroyed the railroad, and the state acquired the right-of-ways, the bridges and highway sections through the Keys extended the route to Key West. The Overseas Highway was born and opened to traffic in 1938.

Start of US1

The present-day route connects roads, starting with Fleming Street at 490 Whitehead Street in Key West and going 2,369 miles to Fort Kent, Maine, on the Canadian border. There’s a monument to “America’s First Mile” there. But who gets to say who has the first and the last, best and worst miles? Obviously, Key West has the best and first, and everyone else has the rest!

Experience The Overseas highway

Bahia Honda Rail Bridge

Driving down the Overseas Highway is a treat, with spectacular views from the bridges that seem unchanged from those Flagler must have enjoyed from his private rail car. Better views of the Keys can be had, of course—nothing beats seeing the Keys from the water. All this railroad and highway stuff is cool, but boating is the only way to experience the Keys like a local. Call Captain Zak today, book a private Key West sunset or sandbar charter, and he’ll show you what it’s all about! 

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