Over-Sea Railroad History Lives on Beyond Centennial
The official Florida Keys Over-Sea Railroad centennial celebration ended Jan. 23 (and it was a great joy to be part of the once-in-a-lifetime event). But even though that date has passed, you can still explore sites, exhibits and landmarks recalling the world-renowned railroad that, in 1912, connected the Keys with mainland Florida for the first time.
Visitors to the Key West Museum of Art & History at the Custom House examine the exhibit commemorating the 100th anniversary of the debut of Henry Flagler's Florida Keys Over-Sea Railroad. (Photo by Andy Newman, Florida Keys News Bureau)
For example, check out “Flagler’s Speedway to Sunshine,” a permanent exhibit at the Key West Museum of Art & History at the Custom House. Fascinating for railroad buffs, history aficionados, kids and anyone who loves the Keys, the exhibit showcases the construction, heyday and demise of the railroad once called “the eighth wonder of the world.”
At the impressive red-brick museum, you’ll find a re-created railway car, a replica section of the Old Seven Mile Bridge that was the Over-Sea Railroad’s centerpiece, vintage footage of the train trip from the Middle Keys to Key West, a film spotlighting railroad creator Henry Flagler and the first train’s arrival in Key West, and MUCH more.
In a new exhibit section, you’ll discover Key West’s Prohibition era, the Great Depression, and even the 1935 hurricane that severely damaged parts of the railroad and helped end its reign. Also featured are the history of Key West’s Casa Marina, the jewel of Flagler’s resort hotels, and even family albums and memorabilia from Ernest Hemingway’s life in Key West during the 1930s.

Railroad and history buffs can visit the former Over-Sea Railroad work camp at Pigeon Key, lying beneath the historic Old Seven Mile Bridge. (Photo by Andy Newman, Florida Keys News Bureau)
The museum is far from the only place you can experience the history of the fabled Over-Sea Railroad — whose track, by the way, stretched more than 100 miles out over open water. Near Marathon in the Middle Keys, a railroad heritage site called Pigeon Key lies beneath the Old Seven Mile Bridge, providing an eye-opening window on Keys life a century ago.
Just over two miles west of Marathon, five-acre Pigeon Key was home to more than 400 workers who built the railroad in the early 1900s. The island was a base camp with a commissary and one-room school during the Seven Mile Bridge’s construction from 1908 to 1912.
Today many of Pigeon Key’s original railroad buildings and houses still stand — and it’s no surprise to find that the tiny, pristine speck of land is listed on the National Register of Historic Places. It also has a museum that chronicles the construction of the amazing railroad, and daily historic tours are offered.

Costumed artists and re-enactors celebrate the debut of Key Largo's mural inspired by the Over-Sea Railroad centennial. (Photo courtesy of Cris Sandifer)
Combine your Pigeon Key expedition with a boat ride by taking the ferry from a visitor center at Knight’s Key, located at mile marker 47 on the west end of Marathon.
Even if you can’t explore Pigeon Key or the Key West exhibit, you’ll glimpse plenty of reminders of the Over-Sea Railroad simply by driving through the Keys on the Overseas Highway — which evolved from the railroad itself. For example, near mile marker 95 bayside in Key Largo stands an intriguing outdoor mural, recently painted by artists from the Upper Keys’ Art Guild of the Purple Isles and Keys high school art club students.
The hand-painted mural measures 60 feet long and 11.5 feet high, and depicts an Over-Sea Railroad passenger train steaming across an arched bridge that looks a lot like the Long Key Viaduct. In the sky is a full moon adorned with the face of railroad visionary Henry Flagler.
And speaking of bridges, it’s easy to spot many of the original railroad bridges alongside the spans supporting the modern Florida Keys Overseas Highway — the contemporary connection from mainland Florida through the Keys — that follows the trail blazed by Flagler a century ago.

