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The Old Mill Inn on Mattituck Creek was known as a good place to get a drink, facilitated by a trap door that could be opened at low tide to allow bootleggers to unload unseen. (Courtesy of The Collection of The Old Mill)

During the 13 years that Prohibition was the law of the land, it was illegal to produce, transport or sell alcoholic beverages in the United States and its territorial waters, but legal to consume them. 

On Long Island, it was never very hard to find a drink.

The land that extends from the Hell Gate Bridge in Queens out east to Orient and Montauk was a 100-mile long dock with coves and harbors where rumrunners could hide after venturing outside U.S. territorial waters to pick up alcohol from the ships of European producers. On fishing boats and skiffs, they ran their cargo secretly to shore, paid by middlemen who sold the booze to bars and speakeasies in New York. 

When the 18th Amendment took effect on Jan. 17, 1920, baymen in the middle of scallop season found they could make big money moving mysterious, compact and very heavy cargo from boats waiting offshore, usually by night.

Enforcement of Prohibition was half-hearted, especially on the quieter North Fork of Long Island. The word “scofflaw,” which means someone who takes advantage of hard-to-enforce laws, came into wide use during Prohibition to describe those who continued to traffic in alcohol, despite the law. Given how unpopular Prohibition was on Long Island, scofflaw was practically a term of endearment.

Not every speakeasy was raided, or even inspected — even if everyone in town knew you could buy alcohol there. The Old Mill Inn on Mattituck Creek was widely known as a good place to buy a drink, and the inn’s website describes a still-existing “drop door near the kitchen of the Old Mill that allowed boats to readily transfer hooch during low tides.” 


In 1926, The Nora, a boat out of Greenport, was seized during a Coast Guard patrol on Mattituck Creek and the captain and crew arrested. No liquor was found on board, but the ship and her crew were moved to New York for questioning based on claims of state authorities that they had information linking the ship to rumrunning. 

Southold historian Amy Folk told the strange story of Patrick Kelley in her 2022 book, “Rumrunning in Suffolk County.” Kelley, a police officer who singlehandedly covered the 400 square miles of Southold, was arrested in 1932 when a hidden trapdoor opening into a tunnel, which in turn led to a storage pit holding 50 bags of rye grain, was found in his home. He and his father were charged with possession of liquor and having an illegal radio transmitter in the house, a device used at the time by rumrunners to communicate with ships carrying alcohol. Kelley got off with a temporary suspension from his law enforcement job, but returned to enjoy a long career with the Southold Police Department. 

The danger and violence that Prohibition brought to Long Island increased significantly in 1924, when the law governing U.S. territorial waters was changed, extending those waters from three to 12 miles from shore. It was an effort to discourage rumrunning that succeeded in discouraging small-time operators, but it fueled the creation of organized rings of rumrunners who used shortwave radios and codebooks to communicate, and bought larger boats with more horsepower necessary for a high-speed chase at sea.

One of the unintended consequences of Prohibition was a spike in violence and crime, especially shootings. On the formerly peaceful North Fork, it hit hard. Claudio’s Tavern and Grill on the Greenport waterfront was constructed in such a way that deliveries of alcohol could be made through a trapdoor in a part of the restaurant that was built out over the water, not far from the Coast Guard Station established to try and enforce Prohibition. The deliveries were then transported to New York, but the owner of the restaurant stopped allowing the smuggling when a driver charged with transporting liquor to New York was killed in 1926.


An especially notorious incident began in the waters off Orient Point around midnight in August 1931, when a Coast Guard patrol boat spotted the Artemis, a boat built especially for rumrunning: 52 feet long, with three high-powered engines that could achieve speeds of about 45 knots (51 mph.) Aboard it were two Greenport residents, Carl Reiter and John Johnson. 

Refusing the Coast Guard cutter’s request to stop, the Artemis took off, with the Coast Guard in pursuit. The patrol boat fired on the Artemis, seriously wounding Reiter and Johnson. The Artemis turned and rammed the cutter, disabling it long enough to land in Orient and get Reiter and Johnson transported to a hospital in Greenport. A doctor at Eastern Long Island Hospital put investigators off the trail of the wounded men by saying they were the victims of a hunting accident.

More than 250 boats were seized for rumrunning by state and federal officials off Long Island during Prohibition, and many of them were owned by North Fork captains. These included the Sylvester, owned by Robert Clark of Greenport, which was seized off Montauk Point with 500 cases of alcohol aboard, and the rumboat Magdalene, owned by Dr. Johnson of Greenport.

Albertus Clark Jr. was about 5 years old when Prohibition started, and 18 when it ended, so his recollections, from a written account at the Shelter Island Historical Society, are vivid and colorful. He lived in what is now the Mashomack Preserve, where his father was a caretaker for Otto Kahn, owner of the large property. Albertus 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. He died in 2014, leaving behind his written descriptions of life on Shelter Island.

Clark described the radio operators who moved into a small house on the Mashomack property, and set up a communication station for bootlegging: “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.” 

There was beauty as well as violence in Clark’s childhood recollections of Prohibition. “There were several boats in the lagoon at Silver Beach and a couple in Coecles Harbor,” he wrote. “They were beautiful to see coming down through South Ferry just at dusk. One got shot up bad and was beached at Nichol’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.”