I've posted this before, elsewhere:
My grandparents summered in Anglesea, at the North end of the island.  My father, born in 1920, remembered the PRR drawbridge up there.  One Sunday morning, he heard a great deal of noise from the boaters directed at the bridge tender, who wasn't letting them by to sail North through Grassy Sound and Hereford Inlet towards the ocean.  The bridge tender said something to them, and many of the "head" boats, who would take "walk up" fishermen, turned around to return towards the Cold Spring Harbor docks.  Shortly after, frantic whistling was heard from the mainland as a train came racing across the meadows.  Normally, they ran slow approaching the drawbridge.  It was the Fishermen's Special, running very late, with the boat customers!  It might have been delayed by problems at the Delair drawbridge.
I wondered why the boats hadn't just used Cape May Inlet at the South end of the island next to Cold Spring Harbor to reach the fishing grounds.  Other sailors have told me that the inlets sometimes get filled with silt, but not always at the same times, so in that year, the boats may have had to sail the long way around to avoid getting stuck.

Jim Boylan