Key West Blog

The History of Trains in Key West and the Florida Keys

Passenger train engine 145 ready to leave Trumbo Station in 1926
Haffenreffer collection Florida Keys Historic Center.


Tracing the Tracks: A Journey through the History of Trains in Key West and the Florida Keys

Welcome, fellow history enthusiasts and curious minds, to another exciting chapter in our exploration of Key West’s rich heritage. Today, we embark on a captivating journey through time, delving into the fascinating history of trains in Key West and the Florida Keys. Join me as we uncover the pivotal role these iron horses played in shaping the region’s development and leave an indelible mark on its cultural fabric.

1. The Birth of the Overseas Railway:
Our story begins in the late 19th century when visionary entrepreneur Henry Flagler set his sights on connecting the Florida Keys to the mainland. In 1912, after years of arduous construction, the Overseas Railway was completed, stretching an impressive 156 miles from Miami to Key West. This engineering marvel, comprising over 40 bridges and countless miles of track, was a testament to human ingenuity and determination.

2. Overcoming Adversity:
The Overseas Railway faced numerous challenges throughout its existence. In 1935, the devastating Labor Day Hurricane struck, causing significant damage to the tracks and bridges. Despite the immense destruction, the railway was rebuilt, only to face another setback during World War II when the government requisitioned the tracks for military purposes. However, the spirit of resilience prevailed, and the railway was restored once again.

3. The Flagler’s Last Ride:
The Overseas Railway’s most famous passenger was none other than Henry Flagler himself. In 1912, at the age of 82, Flagler made his final journey to Key West aboard his private railcar. Sadly, he passed away just a year later, but his legacy lived on through the railway that bore his name.

4. The Demise and Transformation:
Despite its remarkable achievements, the Overseas Railway faced an uncertain future with the advent of the automobile and the increasing popularity of road travel. In 1935, the devastating hurricane dealt a final blow, rendering the railway beyond repair. However, the remnants of this once-mighty transportation system were not forgotten.

5. The Overseas Highway:
In the wake of the railway’s demise, the Overseas Highway emerged as a modern marvel, utilizing the existing infrastructure to create a roadway connecting the Florida Keys. Completed in 1938, this iconic highway, spanning 113 miles, offered breathtaking views of the turquoise waters and picturesque islands, becoming a popular tourist attraction in its own right.

6. Preserving the Legacy:
Today, the Florida Keys still bear the marks of their railway past. The Old Seven Mile Bridge, a testament to engineering brilliance, stands as a reminder of the railway’s grandeur. Visitors can explore this historic landmark, now a pedestrian and cycling path, and marvel at the ingenuity of those who came before us.

As we conclude our journey through the history of trains in Key West and the Florida Keys, we are reminded of the indomitable spirit that shaped this region. The Overseas Railway, though short-lived, left an indelible mark on the landscape and the hearts of those who experienced its glory. Today, as we traverse the Overseas Highway and walk the Old Seven Mile Bridge, we pay homage to the pioneers who dared to dream big and connect this island paradise to the world beyond.