Shelter Island Reporter photo quiz: What is that? Feb. 15, 2025

If you know, let us know. Send your responses to [email protected] or phone 631-275-1859.

Here at the What Is That desk we often refer to the weekly offering as a “mystery photo.” This week we have a true Shelter Island mystery connected to the photo, which we have run before in this space.

In the decade of putting our photos every week here on page 4 in our print edition and online, we have always known where and what the featured photo is. But again, for this one, we’re clueless as to what, or, the deeper mystery — why. We ask again about those shoes attached to the board at the corner of Locust Avenue and Bridge Street: If you know, let us know.

Last week’s photo (see below) was no mystery to Roger McKeon, Ed Hydeman and Carleen Washington.

Roger emailed us to say, “Bootleggers Alley, no doubt: I can even make out Peter’s fish.”

And Ed, on our Facebook page, was also right on the money.

Carleen saw it and it brought back sweet memories: “My dad, Ed Blados, used to spend countless hours fishing there.”  

And Rich Surozenski was all over it, too.

The little lane that starts at the corner of Nostrand Parkway and West Neck Road and dead-ends at a town landing on the bay 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), many Islanders were 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 coast-guards 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.”