It’s hard to imagine the Hamptons without a party. From Montauk to Westhampton Beach, the rosé-all-day vibes, wine gardens and tap rooms are as much a part of summer here as sand on the beach. But only a short 100 or so years ago, this kind of glass-clinking culture was not welcome. At least not publicly.
When, on Jan. 17, 1920, Prohibition went into effect thanks to the Eighteenth Amendment, it became illegal to produce, transport or sell alcoholic beverages in America. On the East End of Long Island, the party never stopped, but it did become stealthier.
The consumption of alcohol on the East End goes back to the first days of European contact, and for as long as people have been drinking alcohol on the East End, groups have tried to put an end to it as much as others embraced its celebratory nature. By 1651, East Hampton passed a local law prohibiting sales of alcohol to young people and servants. Sag Harbor formed a Temperance Society in 1829 and Shelter Island followed suit in 1840. In 1844 the Montauk Sons of Temperance formed, and in the early 20th century, the rise of the Ku Klux Klan on Long Island targeted Catholics, Jews and immigrants in general—groups viewed at the time as having a culture of destructive public drinking.
Geography Was Destiny
When Prohibition became the law of the land, Long Island had more than 1,600 miles of shoreline and that proximity to the sea was handy for something other fishing, as secreted-away spirits flowed in, through and down the hatch. “Its baymen knew [it] knew better than anyone. Just three miles off the South Shore lay a fleet of foreign liquor ships eager to supply the nation’s largest liquor market,” wrote Suffolk County historian Paul Bailey in “Early Long Island: Its Indians, Whalers, and Folklore Rhymes.”
The scale at which Long Islanders were able to flout restrictions against transporting and selling alcohol made it impossible to effectively enforce the new law. Regina Feeney, an archivist at Freeport Memorial Library, is also the town historian and well-versed in Long Island’s Prohibition history. She says that alcohol consumption on Long Island was not deterred during Prohibition, it actually spiked: “In Freeport, one third of all arrests were alcohol-related. There was not a sober person in the village.”
A 1922 headline in the New York Herald crystallized the central conflict between Prohibition and the nautical rumrunners on East End of Long Island: “Must Catch Dorymen—Washington Acts on Reports of Bootlegging Visits Off Long Island Coast.” Before Prohibition was a year old, Long Island newspapers carried accounts of large-scale bootlegging activity, including a boat seized off Montauk with a $1 million cargo of liquor—worth about $18.5 million today.
Large tracts of waterfront property became hot spots for off-loading liquor from boats to cars and trucks for the trip west to New York City. In Montauk, where 10,000 acres owned by entrepreneur and developer Carl Fisher were being made into a resort, Fisher hired men to watch his docks on Lake Montauk to prevent their use for rumrunning. But at Dock No. 2, bootleggers knew that the watchman went out at 1 a.m. to punch the clock, after which the rumrunning could begin.
Margot Bachman, whose father worked for Fisher, was a child when she came to Montauk for a summer in the 1920s, and described what she observed in an oral history collected by Montauk Public Library.
“I remember that occasionally one of the boats would be caught by the alert Coast Guard, and they would have to dump their barrels of whiskey and sometimes bottles into the sea, and the next day, the entire community would be down along the beach, picking up the bottles and trying to pull in the barrels,” Bachman said. “And while my father was still working on the dredging of Lake Montauk, the rumrunners would ask him if he would mind on certain nights moving his pontoons so that they didn’t close the breakwater and they could get their boats in. And he always obliged.”
According to Bachman, her father did not ask to be paid for his favors, and his discretion was not forgotten by the secret spirits purveyors. After lending a hand one particularly stormy night, Bachman’s family awoke to an entire barrel of whiskey waiting on their doorstep.
Fish and Potatoes
Rumrunning did wonders for local economy, as long as you didn’t get caught. Fishermen and farmers with excellent access to land and sea, but little cash to show for it, suddenly had a very remunerative sideline that was not only tolerated by neighbors and local officials, but often encouraged.
In 1930, a potato truck driven by John Geiger of Water Mill had the bad luck to pass the recently elected Suffolk County District Attorney Alexander Blue traveling in the opposite direction on a back road near Eastport. The DA, noticing that the truck seemed heavily loaded and was followed by another vehicle full of men, executed a U-turn and gave chase. Blue and his men found 300 cases of liquor buried under potatoes.
It seemed, though, that DA Blue’s dogged diligence was not appreciated by all: His political career was cut short when the Republican Party declined to renominate him in 1932.
When the Coast Guard stopped the fishing schooner Harold off Montauk Point in December 1932, they found a 1200-ton cargo of cod. But the boat was riding suspiciously low in the water, so they dug deeper and found 600 cases of liquor hidden under the fish.
“Every shanty down there was loaded.”
Milton Miller, a commercial fisherman in Montauk, told a story that shows just how normalized bootlegging became for the fishermen and farmers of the East End. Miller was a teenager during Prohibition, and in an interview for the Montauk Public Library archive, he described what happened after he helped collect unopened liquor bottles that washed up on the beach near his aunt’s home and a federal agent showed up to investigate. When the agent knocked, his aunt was in the midst of browning sugar in her cast-iron frying pan — something she was in the custom of adding to illegal alcohol to improve upon its harsh flavor.
“Aunt Lara she opens her door, and she sees he is a revenue man. Well, of course, she don’t want him staying there. Now, [my family] hid the drinks and frying pan, and [the agents] come in, they see half a dozen Bonackers sitting around and there isn’t any liquor there and nothing on the table. And they said, ‘something’s wrong,’ ” Miller recounted. “Aunt Lara, she looked at the guy and she says, ‘come into my humble home.’ She says, ‘I don’t know who you are, but everybody is welcome into my home.’ And Jesus Christ, that damn revenue guy looked at her and he said, ‘I better get the hell out of here.’ So, he got the word out to the rest of the revenue men, and they all left. And every shanty down there was loaded.”
Beach-combing for bottles was quite popular during Prohibition. Bootleggers Alley on Shelter Island was named in 1975 because it was rumored to have been a landing point for liquor, but the terrain — a long sandy beach in sight of Greenport — makes it more likely that it was a good place to find unopened bottles that had been thrown overboard by a passing rumrunner with the Coast Guard in hot pursuit.
Inspired by Shelter Island’s history of rumrunning, and the windfall it was for the local economy, playwright and musician Lisa Shaw set her 2022 musical, The Prospect of Summer, in a Shelter Island hotel at the height of Prohibition. “It was an economic boon for a lot of people on the East End for the few short years that it occurred. Families, teenagers, everybody was in on the action,” Shaw says. “It was interesting to me that this is what kids did in high school at night and they did very well. There was no stigma to this job.”
The 19th-century art collector and entrepreneur Otto Kahn owned almost one-third of Shelter Island, totalling 1,100 acres, making him the absentee landlord of Miss Annie Nichols, the sole survivor of the family from whom he bought the property. Miss Annie was quite elderly, but still in residence throughout Prohibition, and witnessed the drop-off, storage and pick-up of alcohol from Canada and the Caribbean.
As it went, her barn was full of cases of liquor off-loaded from small boats that benefited from the proximity of the woods to the shore to hide their activity, and a small house adjacent to the barn was a state-of-the-art radio station for communication with shippers and rumrunners off the coast. It’s not clear how much Miss Annie knew about the specifics of the activity around the barn and outbuildings, but she must have suspected something.
Albertus ‘Toots’ Clark Jr. was a bayman from the Clark family of Shelter Island. He was about 5 years old when Prohibition started, and 18 when it ended, so his recollections, from a written account at Shelter Island Historical Society, are vivid and colorful. He lived on the land owned by Kahn, where his father took care of the property in Kahn’s absence. He and his siblings roamed the woods, farmland and creeks of Shelter Island when it was mostly open space, save for the homes of a handful of very wealthy people.
Clark described the radio operators who moved into an outbuilding called “The Little House” adjacent to Miss Annie’s three-story Victorian.
“They strung wires in trees… brought two men to operate the code station, named Pat and Buddy. Us kids, we got well acquainted with them. In a couple of years they had to move because of directional radio antennas — they could be caught — so they set it up on a boat so they could move it every couple days. Pat was code expert between American and British forces in World War I — a real character. He carried a black satchel with gun and cash.”
The East End was preordained to be heaven for rumrunners: remote coves with nothing between them and the fleet of booze-bearing ships but the wine-dark sea, and a fleet of hard-drinking baymen in possession of boats and in need of cash. When you look at sepia-toned photos of the Coast Guard chasing the “fishing boats” that moved the contraband ashore and beaches piled with bottles of hooch thrown overboard or lost in the chase, you can imagine how exciting and lucrative bootlegging made life on the East End during Prohibition. But there was beauty as well as violence in the tellings from voices past.
“There were several boats in the lagoon at Silver Beach and a couple in Coecles Harbor,” wrote Clark. “They were beautiful to see coming down through South Ferry just at dusk. One got shot up bad and was beached at Nicholl’s Point and the crew cut gas lines and set it afire. While burning, the tide rose and it drifted off and sunk off Mashomack.”
