Prohibition Stories: Fishing, Rumrunning & Bootlegging Tales of the Hamptons

I was 16 in 1956 when my dad moved our family to Montauk and at the time there were lots of older fishing boat captains who loved to talk about their experiences during Prohibition. Montauk had been a big rumrunning town in the 1920s. Standing at the soda fountain in dad’s store, I’d overhear one or two at the main counter talking to him, the town pharmacist, about their exploits.

The next year, at 17, I got a New York State driver’s license. And the year after that, at 18, I was old enough to drink. (18 was the legal drinking age then.)Now I could hear these tales down at the bars in the fishing village. I remember to this day some of what I learned from Captain Clancy Pitts, Captains Bob and Frank Tuma and others. As a matter of fact, when I started this newspaper in 1960, one of the reasons I did was to tell some of these stories to the town. I thought they’d like hearing them.

Recently, I was asked what era in East End history I thought was the most interesting. I said it had to be Prohibition. [expand]

At the time the Volstead Act was passed in 1920 banning the sale of liquor, the East End was a very isolated and lonely place. There were farms and farmers, mostly in Bridgehampton and Southampton in the potato farming business, and fishermen, boat captains in Hampton Bays, baymen in East Hampton and more fishing boat captains and their families in Montauk. Avid anglers would come out on the railroad from the city to head out for a day of fishing. As for the villages in the Hamptons, they were small, quiet towns that catered, for the most part, to the wealthy bankers and steel barons who came out in the summertime to their giant summer “cottages.” There were locals working for them as maids, cooks and servants. In the winter, the towns shut up pretty tight.

But Montauk really had a separate story. Around 1900, a group of fishing boat captains from Nova Scotia began to build a raggle-taggle fishing village on the arc of Fort Pond Bay in Montauk. They didn’t own the land they built the village on. It was owned by the railroad. But the railroad didn’t seem to mind. The fishermen brought in catches to piers and docks on the bay that the railroad had built back in the 1880s. One could offload the fish here, pack it in ice, and send it off to the Fulton Fish Market by freight train from Montauk just a few hundred yards from the docks. By 1920, this village included about 60 homes, a store, a school, a post office, a church and two bars, almost all of it built with scrap lumber. None of it is there now. But it was a big Wild West affair back then, beyond the grasp of the control of East Hampton Town. (A scale model of the old Montauk village, built from photos and memories, can be seen at the East Hampton Marine Museum on Bluff Road in Amagansett.)

Imagine now being 18 years old and sitting at the bar in a fisherman’s tavern in MontaukSalivar’s, the Montaukett, Trails’s End, Bill’s Inn, Surf and Sand, Ruschmeyer’s, Ray Bimson’s place—and listening to the talk. It is 1960. There is no T.V. over the bar. Had there been, all you’d get were three stations from Connecticut in black and white, and nobody in a bar was interested in that. You actually had to talk to one another.

“The town got rich those years,” one Captain told me, referring to the 1920s. “Here was Montauk, the end of the road. By day, we went fishing. At night we went rumrunning. The big ships sat offshore just beyond the 12-mile limits. It was our job to head out there in our fishing boats and bring in the hootch. We had half of a coin, maybe half a silver dollar, given to us by some of these gangster types who would drive down the dirt road to the bay during the day. You couldn’t spend that coin, but at two in the morning, you could link it up with the half silver dollar held by the captain of the ship you were told to meet. If you had that match, you were who they would transfer off the boxes to. You’d bring it in in the dark. You’d have friends unload the boxes just before dawn and carry them off into the woods behind the town. There the bootleggers, the gangster types, would load the stuff up into their cars and trucks and drive off toward the city. The cars had panels that hid secret compartments under the floorboards. We’d count the money they gave us. And all we had to do after that was keep our mouths shut.

“One morning, about 6 a.m., I was sitting up on a hill to watch the sunrise over the ocean. Down the other way I could see the bay and the village. And then I heard some popping sounds out on the bay. Coming from the east was one of our speediest fishing boats—it had been outfitted with a huge engine— roaring toward me along the shore, followed by a Coast Guard cutter, guns blazing. The Cutter was slowly closing the gap. But aboard the fishing boat, the men were, one after another, throwing the boxes of hootch overboard. First one splash, then a few hundred yards on another splash. It woke me completely up. And what I did was make a mental note of where those splashes were in relation to the shoreline.

“The two boats shot right past me, and as the fishing boat—captained by a guy who ain’t here anymore—got lighter and lighter, it went faster and faster. They were doing about 25 knots, but speeding up. Now I saw that the fishing boat was pulling away. He was gonna get away.

“Later that afternoon, I was out there with my son and a big net and a rope and we were hauling those boxes up. Neat little profit in that. We broke one box open that night and invited over lots of friends. Nice party.”

“Remember that gunfight out at Deep Hollow Ranch?” This was a second fishing boat captain. “It happened one night. Big time stuff. And people thought that bootlegging was just a small time operation. What we learned the next day was that one group of rumrunners wanted all the hootch in this huge barn. There were hundreds of boxes of it, and the men who had stored it there wanted to fend them off. I heard one person got killed before it was over. I think one of the Dickinson boys—I think it was Shank’s father—had been hired to be out there to guard the stuff, but there was nothing he could do.”

“You know the story about Mayor Jimmy Walker and bootlegging here?”

“Never heard that story.”

“There used to be gambling on Star Island. There was this big casino out there, the Star Island Casino. They built it just down the way from the Montauk Yacht Club. The Casino was a big time gambling operation with dancing girls, crap tables, bands and a dance floor, bootleg liquor and back rooms and stuff. They only let in the gangsters and politicians from New York. But we all knew about it.

“You know those stone guardhouses that are right at the entrance to Star Island Road where it begins at Westlake Drive? The casino is long gone, but the guardhouses are  still there today. They used to have men in them with telephones. If the feds were seen driving up, they’d call down to the casino to get all the back rooms shut down and the gambling tables and liquor hidden away. They’d be just a nice, dry, law-abiding club by the time the feds got down there.

“One day, the word went out to get everything out of sight fast. The Mayor of New York, Jimmy Walker, was in the club. Something would have to be done. He took off his jacket and pretended to be a waiter, towel over his arm and everything. So when the feds broke in, he was just one of the employees and they left him alone. Later, he snuck out the back and went down along the docks to the safety of the Yacht Club.”

“There was the time that big moving van, I forget what the letters on the side said, came up the Old Montauk Highway in the middle of the night filled with hootch and heading for the city. Right out front of where Gurney’s Inn is now, it hit a soft spot in the gravel road and turned on its side. Everything inside broke open. What a mess. There were shards of glass on that road for years after that.”

Here are two stories I was told about East Hampton. Downtown East Hampton was where people in Montauk went to go shopping with all their bootlegging money.

“During that time, there was a pharmacy on the northeast corner of Newtown Lane and Main Street,” an old-timer told me. “It was run by a very proper, church-going local fellow named Emil Rowe. He told me this story long after it was over. One day at five, he closed for the day and walked home to his house on Osborne Lane. He and his wife had planned to have dinner with some relatives in Southampton, so after they got ready, he went out to the garage, opened the garage door and found, piled all the way up to the ceiling blocking access to his car, dozens and dozens of boxes of Scotch whiskey.

“He closed the door and went back into the house. He told his wife that they wouldn’t be going anywhere and he told her why. She called her sister and said they weren’t going to be able to make it. A problem had come up. But she wasn’t telling her about the problem.

“The next morning, Emil went out to the garage and opened it up to find his car right there. All the boxes were gone. Sometime in the night, people had come by and had done so without making a sound. Emil told nobody, but he told me the story after they repealed Prohibition in 1933.”

Here’s my favorite East Hampton rumrunning story.

One night around two in the morning, two East Hampton men drove home from a wild party in Greenport in a black Model T roadster. They were both pretty drunk, and with the late hour and the Shelter Island ferries closed for the night, they had to drive the long way around, down to Riverhead, through Hampton Bays and Southampton and Bridgehampton, and then down Wood’s Lane to the Town Pond where it makes that 90-degree left turn onto Main Street.

Somehow, just after they made the turn, their car slowed down and came to a halt and water began seeping in.

The driver looked out into the darkness. Water was all around the car, about halfway up the door.

“I think, my friend,” he said to his passenger, “we have driven into Town Pond.”

The passenger looked out too. “I think you are right,” he said.

Water was now in enough abundance to be getting into their shoes.

“Tell you what,” the driver said. “You wait here. I’ll go out and get some help.”


The driver pulled himself up and out over the driver’s door and, fully clothed, began to swim off. It took him no more than a few minutes to reach the shore, but by the time he had hauled himself up on the lawn of the town green and gotten out onto the road, he had forgotten what he was supposed to do. He scratched his head. Maybe I should just go home, is what he thought. He lived on Pantigo Road, about a mile away. And so that’s what he did.

Four hours later, at 8 a.m. and the beginning of a bright and sunny day, some children were walking along the side of the road toward school on Newtown Lane and saw this Model T Ford sitting in the middle of the pond with a man in it, fast asleep and snoring softly.

The kids picked up the pace. This wasn’t their problem.

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