Flagler's railroad was hit by the 1935 Labor Day Hurricane, and resulted in this scene... Category 5. Great summary of the hurricane at the NOAA.
"The tracks of the Florida East Coast Railroad were completely destroyed where they crossed between islands and were shifted bodily off their roadbed over long stretches on the Keys. An 11-car train, sent to Lower Matecumbe Key in an effort to rescue inhabitants, was washed from the tracks and only the locomotive withstood the force of wind and tide. "
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