Overseas Highway History – From Rail to Road

Overseas Highway History – From Rail to Road

The Overseas Highway, a marvel of engineering and a testament to human ingenuity, winds its way through the picturesque Florida Keys, connecting the mainland of Florida to the tropical paradise of Key West. Stretching for 113 miles across a series of islands and bridges, this iconic roadway stands as a symbol of perseverance and innovation. But what many travelers may not realize is the fascinating history behind this modern roadway, which was once a railway connecting the keys. Join us as we embark on a journey through time to explore the evolution of the Overseas Highway from rail to road.

The Birth of the Overseas Railway (1905 – 1912)

The Birth of the Overseas Railway (1905 - 1912) - Overseas Highway history

The story of the Overseas Highway begins in the early 20th century when Henry Flagler, a visionary industrialist and founder of Standard Oil, set out to extend his Florida East Coast Railway beyond the mainland of Florida. Recognizing the untapped potential of the Florida Keys, Flagler embarked on an ambitious project to construct a railway that would connect the keys to the mainland. Thus, the Overseas Railway was born.

Construction of the railway was a monumental undertaking, with engineers facing numerous challenges including unpredictable weather, treacherous terrain, and the formidable task of building bridges across the open water. Despite these obstacles, Flagler’s team persevered, and in 1912, the first train made its inaugural journey across the Overseas Railway, heralding a new era of connectivity for the Florida Keys.

The Demise and Rebirth (1935 – 1938)

The Demise and Rebirth (1935 - 1938) - history

However, the glory of the Overseas Railway was short-lived. In 1935, disaster struck when a powerful hurricane swept through the Keys, destroying much of the railway infrastructure and leaving the tracks submerged beneath the ocean. In the aftermath of the storm, the decision was made to abandon the railway, marking the end of an era.

But the spirit of connectivity that had inspired Flagler decades earlier refused to die. In the years following the hurricane, plans were set in motion to transform the remains of the railway into a modern highway that would once again link the mainland to Key West. Thus, the Overseas Highway was born, rising from the ashes of its predecessor to become a lifeline for the communities of the Florida Keys.

The Evolution of the Overseas Highway (1938 – Present)

The Evolution of the Overseas Highway (1938 - Present) - history of the Overseas Highway

Construction of the Overseas Highway began in the late 1930s, with engineers repurposing the railway bridges and causeways to accommodate automobile traffic. Over the years, the highway underwent numerous upgrades and expansions, culminating in the modern thoroughfare that exists today.

Today, the Overseas Highway stands as a testament to human resilience and innovation, offering travelers breathtaking views of the turquoise waters of the Atlantic Ocean and the Gulf of Mexico as they make their way from Key Largo to Key West. Along the route, motorists can stop at charming seaside towns, indulge in fresh seafood, and soak up the laid-back vibe of island life.

Overseas Highway historical facts

Overseas Highway historical facts
  • Construction of the Overseas Highway began in the 1910s under the guidance of Henry Flagler, a prominent industrialist and founder of the Florida East Coast Railway.
  • The highway connected mainland Florida to the Florida Keys, spanning approximately 113 miles.
  • The Overseas Highway was originally part of the Florida East Coast Railway, but after severe damage caused by the Labor Day Hurricane of 1935, the railway was abandoned, and the highway took its place.
  • The highway’s construction was a remarkable engineering feat, involving the creation of numerous bridges and causeways to link the islands of the Florida Keys.
  • One of the most iconic features of the Overseas Highway is the Seven Mile Bridge, which is one of the longest segmental bridges in the world, connecting Knight’s Key (near Marathon) to Little Duck Key.
  • The completion of the Overseas Highway in 1938 revolutionized transportation to the Florida Keys, allowing for easier access to the islands and promoting tourism and development in the region.
  • Over the years, the highway has undergone various upgrades and renovations to improve safety and accommodate increasing traffic volumes.
  • The Overseas Highway offers stunning views of the turquoise waters of the Atlantic Ocean and the Gulf of Mexico, making it a popular scenic drive for tourists and locals alike.
  • In 1982, the Overseas Highway was designated as a National Scenic Byway, further highlighting its significance as a cultural and historic landmark.
  • Today, the Overseas Highway remains a vital artery for transportation and commerce in the Florida Keys, serving as a lifeline for residents and businesses while also attracting visitors from around the world.

Do trains still run to Key West?

Do trains still run to Key West? History of the Overseas Highway

No! Since the devastating impact of the 1935 Labor Day hurricane, the Overseas Railroad linking to Key West was destroyed, rendering it impossible to travel to Key West by train. As of now, the southernmost Amtrak station is located in Miami, Florida.

The Overseas Railroad, which once connected the Florida Keys to the mainland, was destroyed by a hurricane in 1935. Since then, the Overseas Highway (U.S. Route 1) has served as the primary transportation route to Key West. However, there have been discussions and proposals over the years about reinstating train service to Key West.

The history of the Overseas Highway is a tale of transformation and adaptation, showcasing the remarkable ability of humans to overcome adversity and forge new pathways forward. From its humble beginnings as a railway traversing the open waters of the Florida Keys to its modern incarnation as a bustling highway, the Overseas Highway continues to captivate travelers from around the world, inviting them to embark on their own journey through history and nature. As we traverse this iconic roadway, let us pause to reflect on the ingenuity of those who came before us and the enduring legacy they have left behind.

Don’t forget to check out my blog post about why the Overseas Highway is so famous: Overseas Highway – WHY Is It So FAMOUS? 8 Things To Know

πŸ‘ Find out more:

Overseas Highway Florida Keys Travel Guide - 101 best stops by Mark Watson

Explore the finest attractions along the Overseas Highway and Florida Keys with my travel guide, ‘Florida Keys Overseas Highway Travel Guide – 101 Best Stops,’ now available on Amazon. This comprehensive guide is your ultimate companion for those seeking adventure and wonder along THE OVERSEAS HIGHWAY & FLORIDA KEYS! Discover 101 amazing places with convenient ‘Scan QR and go’ functionality for easy navigation.


Pacific Coast - Mark Watson

Mark Watson is a California-based member of a Los Angeles motorcycle club and an avid traveler. He has completed seven full journeys along the iconic Pacific Coast Highway on his Harley-Davidson and is passionate about promoting this historic drive to others. Mark has also explored the Alaska Highway and Route 66, and has authored four bestselling travel guides on Amazon: “Route 66 Travel Guide – 202 Amazing Places,” “Alaska Highway Travel Guide – 202 Best Stops,”, “Pacific Coast Highway Travel Guide – 202 Best Stops”, and “Florida Keys Overseas Highway Travel Guide – 101 Best Stops.”

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