The North Fork’s geography has shaped its history for centuries. During Prohibition, its long coastline, working harbors and maritime economy also made it well suited to a different kind of enterprise: smuggling liquor.
Hallockville Museum Farm will revisit that period Sunday, Oct. 11, with “Prohibition on the North Fork,” an event at The Old Mill Inn in Mattituck exploring a local bootlegging operation that connected a Riverhead farm, Mattituck Creek and the illicit alcohol trade that flourished across the region during the 1920s.
At the center of the story is the Naugles family.
George Naugles headed a rum-running operation that used an inclined railway on the north end of the family farm to haul contraband alcohol ashore, according to historian Richard Wines. Naugles’ brother Stanley and neighboring Polish immigrant families participated in the operation, and Stanley piloted a biplane used by the bootleggers.
The family’s activities were part of a much larger underground economy that developed on the North Fork after the federal government banned the manufacture and sale of alcoholic beverages in 1920.
Southold Town’s own historical account describes rum-running as a significant part of local life during Prohibition. A Coast Guard station was established in Greenport to enforce the Volstead Act, the federal law implementing Prohibition, but enforcement did not prevent residents from participating in the trade.
The town history says “many local people made pin-money unloading illegal liquor from fast boats” and describes shipbuilding and rum-running as helping fuel the local economy before the stock market crash of 1929 and the Great Depression.
Greenport became a link in the rum trade
A detailed, 2020 historic-resource survey commissioned by the Village of Greenport provides an even fuller picture of the illicit industry. The village’s reconnaissance-level historic survey says Prohibition created new employment opportunities in Greenport as residents capitalized on the shortage of legal alcohol in New York.
Greenport Harbor became a link in a supply chain stretching from the Caribbean to New York City. Rum runners brought cargo north, while bootleggers moved the alcohol on to the city. Other participants operated warehouses and shipyards or sold liquor locally through speakeasies, according to the village report.
The trade was not a marginal activity. The Greenport survey says rum-running generated considerable wealth during the 1920s and helped drive unemployment in the village to nearly zero. The report also links the illicit liquor business to an increase in violent crime.
Among the local establishments identified in the survey as a Prohibition-era speakeasy is Claudio’s Restaurant. The underground economy developed against the backdrop of a community already closely tied to the sea. Greenport had long been a center of shipbuilding, fishing and maritime commerce, while steamships and the railroad connected the North Fork with New York and New England.
That combination of boats, experienced mariners and access to the waters surrounding the North Fork made the region particularly suited to the clandestine movement of alcohol.
A Riverhead farm and a Mattituck inn
The Naugles operation provides a particularly local window into that larger history.
Hallockville says the family’s connection to The Old Mill Inn actually predates Prohibition. During the 19th century, the mill was the closest place for the Hallock family to bring grain to be ground into flour, according to Wines. The mills in Riverhead were more than twice as far away.
Decades later, the property became connected to the Naugles family’s bootlegging operation. Wines said profits from the illegal liquor operation and the inn may have helped George Naugles construct a substantial new barn after an earlier barn burned in 1936.
The story also illustrates how deeply rum-running could become woven into otherwise ordinary North Fork life. Farms, boats, waterfront properties and local businesses could all become pieces of an illicit distribution network serving a thirsty metropolitan market.
“The remarkable thing about this history is that the connections are still visible,” Hallockville Executive Director Marianne Della Croce said. “The Naugles family story connects the farm at Hallockville to the Old Mill Inn, to the Long Island Sound and ultimately to the New York City market.”
Prohibition comes to an end
The experiment did not last. National Prohibition began in 1920 after ratification of the 18th Amendment and enactment of the Volstead Act. By the early 1930s, public support had eroded substantially.
The Greenport historic survey notes that growing concern over crime associated with Prohibition helped turn public opinion against the policy. The federal ban was repealed in 1933, bringing Greenport’s rum-running economy and its illegal drinking establishments to an end.
Legal drinking establishments soon took their place. The village survey points to Mitchell’s Restaurant, which opened in a former Front Street automobile showroom in 1933, the same year Prohibition ended.
Nearly a century later, Hallockville is using one of the surviving places connected to the era to tell the story.
The Oct. 11 program will feature Wines and Anthony Martignetti, owner and restorer of The Old Mill Inn, discussing the Naugles family, rum-running and North Fork speakeasies. Guests will be served period-inspired canapés and a choice of three Prohibition-era cocktails, accompanied by live jazz.
“History is often more interesting when you can stand in the place where it happened,” Della Croce said. “The Old Mill Inn gives us an extraordinary setting to tell this story and to look at the North Fork through a very different lens.”
“Prohibition on the North Fork” will run from 4 to 6 p.m. Sunday, Oct. 11, at The Old Mill Inn, 5775 West Mill Road in Mattituck. Tickets are $125 per person and advance registration is required.
Tickets can be purchased on the Hallockville Museum Farm’s website.
