Rum Running on the East End: Shelter Island and North Fork sites were involved

News that the Hallockville Museum Farm in Riverhead and the Old Mill Inn in Mattituck held a presentation recently called “Prohibition on the North Fork,” reminded us of Shelter Island’s storied history of ventures in illegal booze running.

Bootleggers Alley is the short, narrow street at the corner of Nostrand Parkway and West Neck Road that dead-ends at a town landing on the bay. It came by its name because the road served as a popular channel for the buying, selling and transportation of alcohol during Prohibition (or as some termed it, “The Great Thirst”), when in January 1920 the sale of alcohol was banned in the U.S.

Though illegal, the practice of bootlegging along with fishing and farming, helped the Island survive some lean economic stretches, according to the Shelter Island History Museum, with many Islanders grateful for the revenue — not to mention the booze — that bootlegging brought to the community.

Graduate of Shelter Island High School and decorated U.S. Navy Admiral Harold E. Shear once remarked, according to History Museum archives, that when he was growing up on the Island, “The coastguards were considered the bad guys, and the rum runners were considered the good guys.”

The little lane was renamed on January 1, 1975 from Park Place to Bootleggers Alley. Nostalgia for liquor traffic during the dry period led to the welcome official change; before then, sources from the History Museum noted, Bootleggers Alley had likely been an informal nickname.

The Long Island Traveler-Mattituck Watchman reported on January 15, 1975 that, “Unlike other street name changes, there was no opposition to this one.”

Across the bay during Prohibition, the Old Mill Inn became part of the Naugles family’s rum-running operation. They operated an inclined railway on the north end of their farm that was used to haul up contraband alcohol. George Naugles was the leader of the operation. His brother Stanley, as well as neighboring Polish immigrant families, were also involved. Stanley piloted the biplane they used in the operation.

“Profits from the bootlegging operation and from the Inn probably enabled George to build such a nice new barn after his old one burned in 1936,” said Hallockville Historian Richard Wines.