The term “boot-legging,” it is suggested, originated during the Civil War when soldiers would sneak liquor into camp in their boots. Civilians quickly took up the practice, hiding flasks in boots or trouser legs. The term stuck and expanded to include “rumrunners,” smugglers waiting offshore with their illicit swag.

With Prohibition, Fire Island awoke to a new reality. It lay close to New York City, the biggest market for this new, illegal contraband. With its long stretches of beaches, sparse population, ideal topography, and numerous inlets (in particular the relatively safe Fire Island Inlet), Fire Island became an ideal location for smugglers just as it had been for the pirates of yore.

Depending on which history book you read, either Bill “The Real” McCoy or William “Big Bill” Dwyer came up with concept of Rum-Row, a flotilla of large vessels (mother ships) stationed three miles off-shore in international waters. They would sell their illegal spirits to smaller, faster boats for transport to trucks waiting to take the hooch to market.

The infamous hotel, the White House, in Water Island, once the destination for the socially elite (including President Teddy Roosevelt it has been rumored), had fallen on hard times after the First World War. Prohibition gave it new life and it returned to its glory days as a speakeasy and gambling casino. Even sleepy Saltaire had its “casino,” which openly served liquor.

One self-confessed bootlegger specified Long Cove, Lonelyville and Ocean Beach as the primary destinations for the majority of the illegal liquor. Some of the more renowned speakeasies included the Canoe Place Inn (CPI), aka Tammany Hall East, because of all the corrupt politicians who hung out there, and Claudio’s of Greenport, which still has a trap door behind the bar for access to illicit spirits floated in beneath the building.

Several Fire Island ferry boats enjoyed exciting lives as rumrunners before retiring to more sedate occupations. Just about all old-salt captains from the various Fire Island ferry lines claimed to have been rumrunners during Prohibition. The ferry “Running Wild” and many other boats plying the bay in the ‘50s and ‘60s had been ferrying illegal booze before they began ferrying passengers. The “Running Wild” still had patched-over 50 caliber machine gun bullet holes in its hull when it was sold to a gentleman from Sayville.

Information sourced from Fire Island News- Learn More Here