They said it couldn’t be done – building a railroad across the open waters to Key West. Yet Henry Flagler, the visionary Standard Oil tycoon and developer of Florida’s east coast, made it a reality.
Overseas to the Keys: Henry Flagler’s Oversea Railway takes visitors on a journey along the Florida East Coast Railway’s Key West Extension, an extraordinary feat of engineering that connected mainland Florida to Key West by rail. Flagler invested more than $30 million of his own fortune in the project, transforming what many considered an impossible dream into one of the nation’s most remarkable transportation achievements.
The tracks are gone today, destroyed by the devastating Labor Day Hurricane of 1935. But much of Flagler’s railroad right-of-way lives on as the foundation of the present-day Overseas Highway. The railway’s legacy remains woven into the landscape, communities, and identity of the Florida Keys.
Through a compelling mix of historic artifacts, film, photographs, and firsthand accounts from railroad workers and Key West residents, the exhibition reveals the extraordinary human stories behind Flagler’s great engineering enterprise. Visitors discover how Flagler’s civil engineers developed innovative techniques and technologies to overcome formidable challenges of constructing bridges, viaducts, and track across the Florida Keys. More than 4,000 workers labored in difficult and often dangerous conditions, battling heat, mosquitoes, isolation, and the unpredictable forces of the sea.
The exhibition also brings to life the moment the impossible became reality. On January 22, 1912, Henry Flagler arrived by train at Key West, marking the completion of the Oversea Railway and a transformative moment in the history of the Florida Keys. Photographs and contemporary accounts capture the excitement surrounding Flagler’s arrival and the profound changes the railroad brought to Key West and the communities along the route.
Drawing from the Society’s permanent collection and objects from the Bramson Collection, Overseas to the Keys invites visitors to look anew at Flagler’s railway – not simply as a vanished railroad, but as a lasting legacy of ambition, innovation, perseverance, and place. More than a century later, the engineering marvel Flagler built continues to shape how people travel through, live in, and understand the Florida Keys.
