The Overseas Highway: A Fantastic Roadway With a Spectacular History

The Overseas Highway as seen from a kayak across crystal clear water

The Overseas Highway is a fantastic road to drive on today. A modern roadway, surrounded by turquoise water and palm tree lined islands is a fantastic drive now, but it wasn’t always that way. A road that many people take for granted started as a railway, which itself was an engineering marvel in its time. It was such a feat that skeptics called Henry Flagler’s vision for a railroad connecting Florida Mainland to Key West a “folly”.

The Overseas Railway

The pedestrian bridge to Pigeon Key with palm trees and turquoise water

In the late 1800s Henry Flagler was a wealthy entrepreneur who founded a little company that you might have heard of, Standard Oil. He was always on the lookout for ways to make money, because if you think about it, how far could that oil money really get you? Flagler’s ears perked up when he got wind of a small project in Central America, the Panama Canal. Henry figured that once the Panama Canal was completed, that would mean booming business for Key West. He was banking that Key West would become an international deep-water port featuring trade with Cuba and South America. The only problem was that, the only way to get to Key West, or any of the other Keys for that matter, was by boat.

In 1904 Flagler employed surveyors and engineers and started the construction of the Overseas Railway. Thousands of workers poured tons of concrete, built 32 bridges, and filled in miles of low areas with fossilized coral. Over the course of 8 years, 128 miles of track were laid at a cost of over $50 million. Finally on Jan 22, 1912, Henry Flagler and his wife arrived in Key West on their luxury train, the first to complete the Miami to Key West extension.

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The booming business that Flagler thought the completion of the Panama Canal would bring to Key West never materialized and, coupled with the Great Depression, it put the East Coast Railway in financial trouble. The category 5 hurricane of 1935 was the death blow for the railway’s Miami to Key West line after it wiped out several miles of tracks and killed over 400 people.

The Beginning of the Overseas Highway

The Overseas Highway built on top of the old Overseas Railway

The State of Florida bought the right of way for $640,000 and proceeded to build a road on top of the railroad bed. For the bridges, since they couldn’t build the road wide enough through the trestles, they just built the road on top of the trestle. For an example of this see the bridge in Bahia Honda State Park, pictured above. While it saved money and time, the new road was narrow and was a white-knuckle ride when large vehicles were coming at you, but when it opened in 1938, you were just happy to have a road completed.

While it was possible to drive a car from Key Largo to Key west in 1928, it was a long trip. It would take four hours just to get from Marathon to Big Pine Key by ferry. The road was rough and there were multiple ferries across the Keys that you had to take.

By 1982, 37 of the original bridges were replaced with wider, modern bridges to form it into the roadway that you travel on today. When they rebuilt the Seven Mile Bridge, they rerouted it, so it passes by Pigeon Key, instead of over Pigeon Key. Oh, and they didn’t blow up the bridge in the movie True Lies, that was a miniature model that was blown up. The Overseas Highway is still mostly two lanes with an occasional passing lane (not that those offer any relief).

The Overseas Highway Today

Ground view of the old Overseas Railway and the Overseas highway as the converge in the distance over turquoise water with fossilize coral in the foreground

You can still access the old railway today as parts of it were converted into fishing and pedestrian bridges. You can walk up to the gap in the old bridge at Bahia Honda State Park, it gives you an idea of how narrow the road used to be. Walking or biking the newly refurbished two-mile section of the old Seven Mile Bridge to Pigeon Key is a pleasure. While you’re there, take a tour of the now preserved buildings. You can see where and how the workers lived during the construction of the railway and road.

Today, there are 42 bridges and 1 Fred the Tree along the 113-mile span of the Overseas Highway, and in 2009 it was designated as an All American Road by the US Federal Highway Administration. So, while you’re cruising down the highway, enjoy the view, enjoy the breeze, enjoy the history, and don’t worry about the person in front of you going 5 miles under the speed limit.


Keep your notes and things to do while you’re on your trip handy with this wonderful journal. Bonus! There’s a slight imprint of the cover photo on each lined page.


About Randy Folta

Traveler, storyteller, and creator of AdventureFLKeys.com and GetOutAndAdventure.com. I share authentic guides to the Florida Keys, national parks, and beyond — blending adventure and photography to inspire your next journey.