A recently published book, Smugglers, Bootleggers and Scofflaws: Prohibition and New York City by Ellen NicKenzie Lawson, contains an amazing 1924 aerial photo, purporting to show rum-smuggling submarines in the Hudson River near Croton Point. The photo appears in the chapter “Rum Row”—the name of the smuggling area of the Atlantic coast from Nantucket to New York City and New Jersey. Lawson writes,
“News of a submarine being used on Rum Row appears to have some substance to it. One smuggler testified in court that he saw a submarine emerge on the Row with a German captain and a French crew. Newspapers in 1924 reported that submarines were smuggling liquor to New Jersey and Cape Cod. An aerial photo, taken by a commercial Manhattan map-making firm that same year, suggested submarines were thirty miles up the Hudson River near Croton Point. (German submarines were kept out of the river during World War I by a steel net strung low across the bottom of the Narrows.) The photo purported to document two submarines below the surface of the Hudson River, each 250 feet long and 600 feet apart. The aerial firm sent the photograph to the U.S. Navy, which had no submarines in the area, and the startling image was given to Coast Guard Intelligence and filed away.”
Here’s a link to the book on Amazon, which includes the Rum Row chapter.
Thanks to the New York History Blog, which alerted us to this book with their recent review.
CROTON 
“Interesting,, very interesting.” My soon to be distributed Crotonville memoir addendum includes a photo showing the 1922 crash of a rum-running airplane on a “Crotonville farm.” My caption includes peerless commercial Hudson River fisherman, Henry Gourdine, remembering rum-running boats making nocturnal deliveries to Ossining’s old coal docks. — Tom Neff
Can you email me the photo? I’m wondering if the photo was mislabeled and is the same plane that crashed near Tumble Inn.
To mcheshire: Before I distribute copies of my memoir addendum – free of charge – with this photo I must be certain of copyright agreements. And, Croton and Crotonville are often confused as my research indicates, as has been the case, for example, with the Black Horse Tavern and a photo of Helen Barolini. Although I will be giving up an eye-catching photo for my effort, I am certainly willing to share my find with Croton Friends of History, a fine group I have communicated with through Carl Oechsner. Carl has a copy of my original memoir.
— Tom Neff
mchesire: Further research on my part revealed a newspaper item with date and landowner’s name matching Tumble Inn plane crash. I will delete this photo from my memoir, and it will be good follow-up substance regarding your rum-running submarine item.
1924 was also the year the Democratic Party Platform included a hand-wringing plank about the epidemic of heroin addiction among youth (now that beer was hard to find). Economic consequences took a long time to sink in.