The Overseas Highway offers history lessons, stunning scenery and plenty of driving joy | Great American Roads

Photography by David S. Wallens

Okay, we’ll admit it right off the bat: The Overseas Highway isn’t the most thrilling road this country has to offer. There are no sweeping turns or snow-topped summits to cross; instead, this mostly two-lane highway is a straight shot over the flattest of landscapes. The views, however, can be stunning, with jewel-colored ocean waters cradling tiny, palm-studded islands in the distance. Better yet, traveling down this road is a firsthand way to experience a bit of American history—and get some sun at the same time.

A little more than a hundred years ago, a man named Henry Flagler had a dream to connect Key West, Florida, to the American mainland via rail. The Panama Canal was becoming a reality, and Key West was the closest American deep water port. In Flagler’s eyes it was a boom town waiting to happen.

There were some obstacles to overcome first, including the fact that there was no continuous land between the island of Key West and the U.S. mainland, over 100 miles away. (Cuba is actually much closer to the lower 48’s southernmost city.) Flagler had an ace up his sleeve, however: money, and lots of it, thanks to his founding partnership in Standard Oil. Yeah, he was loaded.

Flagler’s East Coast Railway started construction on the Overseas Railway in 1905 and moved nearly 18 million cubic yards of earth, built 17 miles of bridges, and filled in some 22 miles of waterway. Steam power mixed with sweat on a daily basis during the construction of the 128-mile rail line. 

Regular obstacles included hurricanes, mosquitos, bootleggers, harsh terrain and a complete lack of air-conditioning. The project seemed so far-fetched that many called it Flagler’s Folly. He reportedly dumped some $50 million into the effort.

In 1912 Flagler personally showed the world that his dreams weren’t for naught when he rode on the first train to cover the entire extension. Over the next four years crews worked to fortify the project, replacing wooden trestles with concrete viaducts and building up the earthen berms.

Afraid of heights? Then you probably wouldn’t have enjoyed the original Overseas Highway. Converting the original railway to a highway was done quickly and efficiently, and in some cases—like the Bahia Honda bridge—the roadway was simply laid atop the old train trestle’s superstructure.

While you’re in the Keys, save some time for a visit to Bahia Honda State Park. The Overseas Railway was built spanning a series of small islands, or keys (from “cayos”, the Spanish word for small island), and the park occupies most of the one called Bahia Honda. It offers a world-class beach—in fact, Conde Nast Traveler voted it the best beach in the continental U.S. in 1992. Snorkeling lessons and equipment rentals are available. The beach also offers a great view of the Bahia Honda Bridge, built in 1912 and converted to a roadway in 1938. Once it was decommissioned, a span was removed to facilitate boat traffic.

And here’s the whole reason why Flagler built the Overseas Railroad: Key West. The city never really became the international port that Flagler envisioned, but it’s a nice place to visit thanks to the interesting sites, wonderful seafood and active nightlife.

Mother Nature proved tough to conquer, though, and thanks to her the Overseas Railway survived barely more than two decades. The Labor Day Hurricane of 1935 struck the upper Keys on September 2 as a Category 5 storm, destroying several miles of railway and causing widespread devastation and loss of life. Among those killed by the storm surge were 259 World War I veterans who were working in the Keys on a highway project.

The bridges all survived, but the Florida East Coast Railway, which was in receivership at the time, couldn’t afford the necessary repairs to the rail lines. They sold the right of way back to the state of Florida for $640,000. 

The state simply replaced the railroad with a highway, eliminating the need for the project that the veterans had been building. The new road opened in 1938. The original Overseas Highway used the same bridges and trestles built by Flagler’s crews; in many cases, the narrow two-lane highway was simply perched atop the railroad trestles. 

The Keys offer world-class fishing that has attracted the likes of Ernest Hemmingway and Zane Grey. Flat, reef and deep-sea fishing are available, and charters are only a phone call away. Want to do some fishing on the cheap? Bring your gear and drop a line from one of Flagler’s spans. Even though new bridges have been constructed, the originals were often left as fishing piers.

The road served its purpose in that people could finally drive a car from the Florida mainland down to Key West, but it was a somewhat harrowing trip in anything much larger than a small sedan. (For a visual, picture two 1960s-era motorhomes trying to pass each other on a narrow two-lane bridge that’s some 50 feet up from the water below.)

Relief came during the 1980s as modern, wider bridges replaced many of the original artifacts. It’s still a two-lane road for the most part, but the new causeways and bridges at least feature a little bit of elbow room. (By the way, a section of the original Seven Mile Bridge was blown out during filming of the Arnold Schwarzenegger film “True Lies.”)

In 1928 it was possible to drive to Key West, but the trip involved a couple of ferries. It wasn’t a quick journey. The desire for better bridges, plus a need for jobs for out-of-work World War I veterans, led to a massive bridge-building project that started in late 1934. 

A Category 5 hurricane made landfall at Craig Key on Labor Day, 1935, and left a path of destruction across the Upper Keys. The storm’s toll included miles of Flagler’s railroads and, worse, several hundred lives. The official death toll included 259 veterans and 164 civilians. After the storm, the veterans’ highway project was abandoned as the work shifted to focus on converting the former railroad to roadway. These unfinished piers just off Lower Matecumbe Key were left as a memorial to the lives lost.

Today’s Overseas Highway is a fairly modern route that’s pretty easy to find. From the mainland U.S., head east until you hit I-95; then go south. Hop on the Florida Turnpike in South Florida and stay on it until the end, then pick up U.S. Route 1 and go south. Once you hit Key Largo, you’re in the Keys. Since most Key West destinations are on Route 1, mile markers are often used as reference points.

Like we said, the Overseas Highway isn’t going to produce tire-squealing thrills or apex-clipping drives. It is, however, an up-close look at one of the century’s engineering marvels.


Bahia Honda State Park

Florida East Coast Industries

Hawk’s Cay

Monroe County Tourist Development Council

No Name Pub

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Racerboy1a New Reader
8/4/22 12:47 p.m.

The wife and I have traveled the Overseas Highway many times including our first trip in 1972 when the old narrow bridge was in service.  It was certainly a "white knuckle" moment every time you met an oncoming truck.

Years later when we became snowbirds, and the new bridges were in place, we did it in a 38' diesel pusher motorhome for several winters.  The Keys are a different world and great place to visit. Bahia Honda is awesome.

One more thing, we discovered that there used to be an SCCA Solo 1 down there that used a section of abandon road near Summerland Key.  I don't think they do that anymore.

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