Street Smart: Bootleggers Alley

How much do you know about the streets and roads of the Island?
How much do Island residents really know about the streets and roads we traverse each day? This is the first in a series to unravel the mystery of their names.

Bootleggers Alley is a 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 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 Historical Society (SIHS), 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. naval officer Admiral Harold E. Shear once remarked, according to SIHS 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 street 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 SIHS noted, Bootleggers Alley had likely been an informal nickname.

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