The Hamptons Secret History of Rum Running

It’s hard to believe that the East End, which has become a go-to winery region in recent years, was once “dry.”

Under the 18th Amendment to the Constitution, the production, sale, and transportation of alcoholic beverages became illegal. In 1920 when Prohibition began so did the rum-running and bootlegging. Prohibition created a black market industry for alcohol and a way for some farmers, who could barely make ends meet, to make a living.

The growing business attracted Bridgehampton schoolboys who became involved in the dark world of booze, cash, and illegality. During World War I there was increased support for Prohibition from the middle class. Many thought Protestants were highly supportive but it was later found that many Catholics and Protestants were rumrunners themselves. The industry and operation were very secretive and even today people won’t name names of who was involved.

Locals who lived on the East End year round were a big part of the rum-running and bootlegging business and process. Montauk fishing boats would travel three miles off the shores of Long Island into International waters and anchor to wait for a Canadian transport boat that held alcohol from Canada (where it was still legal). When the alcohol was transported onto the U.S. fishing boats they would motor back to small marinas and unload their goods onto trucks. The trucks would transport the goods from the marina to local barns to stay over night. This became known as “rum-running.” For every case that a farmer would store, they would be paid $1. Sometimes these farmers would hold up to 500 cases at a time, in which case they would earn $500, a hefty profit during the Great Depression. The next day the cases would be loaded on a truck and would be driven to New York.

Soon after rum-running started, so did bootlegging. With so many local potato farms, it was easy to get your hands on the ingredients to make homemade alcohol. A recipe for whiskey was very easy and popular: Take rye and a lot of sugar in barrels and let it ferment. Put the fermented mixture on the stove and wait until it steams at 180 degrees, that’s when you know when it has turned to whiskey because whiskey steams at 180 degrees. It was very common to add sugar and honey to make it sweeter and easier to drink. Usually after people added sweeteners the proof was around 90 to100.

The imported alcohol from Canada provided by the rumrunners and the illegally made alcohol from bootleggers demanded an outlet. This demand was met when speakeasies started to pop up on the East End. The Sag Harbor Turnpike had a strip of speakeasies: Parson’s, Turnpike Tavern, and Nick’s, to name a few. Often you’d find farmers at speakeasies after a long day’s work. These speakeasies only had tables and chairs, and bottles were hidden from view. Contrary to popular belief, not all alcohol was illegal. Pharmacies carried alcohol for medicinal purposes but a prescription was needed.

When rum-running and bootlegging became a high profit business things started getting more complicated. Mob bosses started getting involved for the money. Because of the high demand for alcohol, bootleggers started making it in bulk. Federal agents would trace large shipments of sugar to farms and would often discover huge silos of alcohol. Speeding rumrunners were prone to car accidents. Bystanders might loot the truck of all the alcohol. Sometimes hijackers would threaten the truck drivers’ lives and would steal the truck and the alcohol.

In 1930 when Prohibition was over the black market for alcohol ended, and so did the corruption, rum-running, and bootlegging.

To read more about local history, including East End rum-running, bootlegging and farming, check out Ann Sandford’s book Grandfather Lived Here – The Transformation of Bridgehampton, available locally and online.

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