With shorelines allowing easy travel and its proximity to New York City, Long Island — otherwise known as “Liquor Island” — played a significant role in rumrunning during Prohibition.
In a new book set for release in June, Southold Town Historian Amy Folk explores rumrunning in Suffolk County during the nationwide ban on alcohol that lasted from 1920 to 1933.
Ms. Folk said her focus was originally rumrunning in Southold, but her publisher asked her to expand her research. The title will join a roster of other local history books partly penned by Ms. Folk, including “Hotels and Inns of Long Island’s North Fork” and “Murder on Long Island: A 19th Century Tale of Tragedy & Revenge.”
While describing her work, Ms. Folk emphasized that there’s a difference between rumrunning and bootlegging. “Rumrunning for me is when you go from the boats on Rum Row, and you take a ship, a really fast ship, and you bring the liquor into shore,” she said. “And then the bootleggers pick it up. And they’re the ones who run it by vehicle up to the city or to its destination.”
Prohibition was enforced by the Coast Guard and eventually the Department of Justice — not local police officers, according to Ms. Folk. According to History.com, the federal government initially assigned enforcement to the Internal Revenue Service and later transferred the responsibility to the Justice Department and Bureau of Prohibition.
The industry marks the start of organized crime in the U.S., birthing groups that would eventually become versions of the mafia, according to Ms. Folk. Smugglers netted millions, at a time when a pound of coffee cost around 35 cents, she said.
Ms. Folk estimates she’s spent about two years writing the book, although she said she has spent at least three or four talking about it. She finally put pen to paper during the pandemic.
Her research was inspired by a “fascinating” codebook residing with the Oysterponds Historical Society, which she came across after delivering a lecture on rumrunning “maybe five, seven years ago now.” A friend encouraged her to put stories to the code and Ms. Folk started to investigate, relying mainly on old newspapers and interviews.
“There are other stories that I didn’t use that people around there have told me. They limit you and how much you can put in these books, so I had to do a little picking and choosing here and there,” she said. The Long Island rumrunning industry has also inspired a host of local lore, although Ms. Folk emphasized she practices responsible history; only verified stories have made it into her book.
One bootlegger trying to sneak booze past federal agents, she recalled, bought an oil truck to smuggle his wares up-island. He spotted a pair of agents on his journey and turned around to hide, eventually painting the truck to disguise it.
“He gets pulled over on Lake Grove and the two guys are like, ‘There’s something wrong with this guy, but we’re not sure what it is.’ And they’re going over the whole oil truck and they can’t figure it out,” Ms. Folk said. The agents asked the smuggler to fill up their tank, and he pointed out that it was still half full. “As he pulls away, the two officers are talking about their encounter with this guy. And one of them said, ‘Did you notice that he had wet paint on his pants, the same color as the truck?’ And they were like, oh, and they went tearing after him.”
Bootleggers Alley, the short, narrow street at the corner of Nostrand Parkway and West Neck Road that 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.”
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.
Another story Ms. Folk researched for her book involves “a famous boat incident” in Southold with a ship called the Artemis. The Coast Guard asked to board the ship and instead of stopping, the captain gunned the engines. He had a steering system that allowed the crew to lie flat as they drove the boat, while the Coast Guard opened fire.
The captain and another crew member were hit, so when the ship ran aground at Orient Point, the crew took them to Eastern Long Island Hospital and broke up their cargo at local homes. The Coast Guard did manage to take some of the alcohol, but not all of it.
While the ship was repaired in Port Jefferson, investigators visited the hospital to ask about the shot-up crew members. “A quick thinking doctor said, ‘Oh, no, it was a hunting accident. These guys have been here for a while, nothing to do with that.’ And the doctor managed to save the two of them from being arrested,” Ms. Folk said.
Although some locals did not willingly participate in the smuggling trade, many were “more or less forced into it,” while others wanted to be part of it or were willing to ignore it. “A lot of times, if you had a shoreline house and somebody came around and said, ‘I need to borrow your garage for tonight, don’t go in it,’ a lot of people would just say, ‘O.K., go do whatever you’re going to do,’ because they know they’re sort of a violent group of people, right?” Ms. Folk said.
A whole bunch of alcohol might appear and then disappear, leaving only perhaps a bottle or two to mark its passing.
Occasionally, people would turn the smugglers in. A Greenport woman, upset with her rumrunning husband drinking away his salary, approached his bosses to ask for at least part of it to live on. They laughed at her, so she helped break up the ring.
She was later hired as an investigator, after starting out as an informant with her husband, who turned up six months later with a bullet in his head. “I don’t know if they ever managed to pin it on anybody,” Ms. Folk said. “But, I mean, a lot of these guys that these rings are working for, are names that, if you ever looked at organized crime, would be Lucky Luckiano, Dutch Schultz, Waxey Gordon.”
“We only really missed Al Capone because he moved to Chicago like two years before Prohibition started. He would have been part of these too,” she said.
Ms. Folk has been giving lectures on rumrunning in Southold and Suffolk County already — the descendant of a rumrunner from the Artemis approached her after one — and she has another coming up on May 10 at Peconic Landing before the book comes out.
She’s encouraged people to record their family stories. “There’s all these stories that I would love to collect, but people need to write them down,” she said. “Rumrunning in Suffolk County: Tales from Liquor Island” has an expected release date of June 20.