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You're interested in the Flagler Railroad. It was built by Henry Flagler between 1905-1912, connecting Miami to Key West. The railroad was a significant engineering feat, but was destroyed by a hurricane in 1935 and replaced by the Overseas Highway. Its legacy remains in the Florida Keys and is preserved at the Flagler Museum.

Did the Flagler Railroad actually run before the hurricane destroyed it?

Flagler Railroad Operation

Yes, the Flagler Railroad, also known as the Florida East Coast Railway's Key West Extension, did operate before it was destroyed by the hurricane.
The railroad was completed on January 22, 1912, and it began operating on the same day, with the first train arriving in Key West.
The railroad operated for over 23 years, providing a vital transportation link between the Florida Keys and the mainland.

Hurricane Destruction

On September 2, 1935, a devastating hurricane, known as the Labor Day Hurricane, struck the Florida Keys, destroying much of the railroad and killing over 400 people.
The hurricane's powerful winds and storm surge destroyed many of the railroad's bridges, trestles, and tracks, making it impossible to repair.
The railroad was eventually replaced by the Overseas Highway, which was built using many of the railroad's original bridges and routes.