Claudio's restaurant in Greenport on Jan. 27.

Claudio's restaurant in Greenport on Jan. 27. Credit: Randee Daddona

Prohibition, that "Noble Experiment" in American history, was the law of the land from 1920 until 1933. But in that short span, it led to some of the wildest and most lawless of times in America’s history. Long Island turned into a crucial highway in the efforts to smuggle alcoholic beverages to a thirsty citizenry. Baymen and boatwrights, bar owners and bankers, joined in the frenzy to make money from the booming trade in illicit booze.

Long Island — with its long, sinuous coastline punctuated with countless secret coves, harbors and beaches — attracted a flotilla of smuggling ships which made up "Rum Row," as that constant parade of vessels parked just outside the territorial limits off the South Shore was called. Their cargoes were whiskey, rum, rye, champagne and just about any other intoxicating beverage imaginable. New York City alone had an estimated 30,000 speakeasies while Nassau and Suffolk were dotted with bars, roadhouses, resorts and restaurants, like the Cove Inn in Port Washington and Claudio’s in Port Jefferson where drinks could be easily had from secret stashes.

Prohibition created its own enduring Roaring Twenties folklore and inspired F. Scott Fitzgerald’s The Great Gatsby, set on a fictionalized North Shore within communities of "West Egg" [Great Neck] and "East Egg" [Sands Point]. Gatsby, after all, got the money for his palatial West Egg mansion from bootlegging.

In real life, Prohibition also made Big Apple mobsters like Frank Costello, William "Big Bill" Dwyer, Meyer Lansky and Charles "Vannie" Higgins rich and powerful as they plied their smuggling businesses throughout Long Island. They could rely on seaplanes flown out of Curtiss Field near Mineola and secret radio stations on the Shore and North Shores to guide their boats to safe rendezvous with the bigger smuggling ships. The money those legendary gangsters made during Prohibition helped make the mob the power it became in American history. There were also colorful, fabled bootleggers like William McCoy and his lady friend Gertrude Lythgoe, dubbed "the Queen of Rum Row," who plied the smuggling routes from the Caribbean and reportedly offloaded their cargoes on the South Shore. McCoy’s liquor was so good it inspired the phrase "the real McCoy."

Claudio's in Greenport during Prohibition.

Claudio's in Greenport during Prohibition. Credit: Claudio’s

Hans Fuhrmann of Greenport would leave his wife Annie for days on end to crew rum running ships and drink up a storm—until she became fed up and turned him in to federal agents. As it turned out, the Ku Klux Klan on Long Island tried to help federal agents uncover smuggled liquor. But the trade continued as the smuggling led to corruption of police and local public officials as well as gun fights, murder and mayhem.

The 21st Amendment in 1933 repealed Prohibition following a groundswell of opposition, including that of a local women’s group led by Betty Fleischman Holmes of Port Washington. The events, locales and personalities of that period still remain a part of Long Island’s enduring cultural and political history.

1) Montauk Point

Frank Costello became one of New York City’s most prominent rum runners in Prohibition. Like many major mobsters of the era, such as Charles "Lucky" Luciano, Meyer Lansky and Dutch Schultz, Costello amassed a fortune from bootlegging and later plowed some of the money in slot machines and gambling operations. To set up smuggling routes through Long Island, Costello made trips to as far out as Montauk Point and waited in his car while underlings made arrangements for the delivery of booze on the beach. Costello also traveled to Babylon with some bootlegging friends with the idea of buying some property.

The Montauk Point Lighthouse in Montauk.

The Montauk Point Lighthouse in Montauk. Credit: Randee Daddona

2) Freeport Point Boat Yard

Started by Fred Scopinich and his brother Mike in the 1930s, the boat yard designed and constructed fast skiffs for rum runner and pursuit boats for the Coast Guard, effectively playing both sides in the war against bootlegging. The rum runner vessels had more powerful engines capable of doing 35 miles per hour while the Coast Guard was restricted by government specifications to engines limited to 25 miles per hour, according to Scopinich’s son, Fred Jr. The rum runner boats also were made bullet resistant through the use of sand between the walls of the pilot house and were outfitted with the capability to spew smoke screens, said Fred Scopinich Jr. Among the clientele of the yard were Dutch Schultz, Long Island bootlegger Rudolph Wylk and noted Brooklyn gangster Charles "Vannie" Higgins. In the 1950s, the yard was moved to East Quogue where Scopinich, now 93, runs a boat building and marine maintenance business.

The Scopinich family in 1945 when their shipyard was in Freeport.

The Scopinich family in 1945 when their shipyard was in Freeport. Credit: The Hamptons Shipyards, Inc./Fred Scopinich, Jr.

3) Cove Inn, Port Washington

This Old World style hotel occupied space at the intersection of Main Street and Shore Road. It gained notoriety when in December 1923 police raided the inn, arresting the owner and bar tender and seizing quantities ale, beer and liquor. The inn was demolished in the 1930s.

A police raid at Cove Inn in Port Washington.

A police raid at Cove Inn in Port Washington. Credit: Port Washington Public Library

4) Dietz Estate, Mill Road, south of Hempstead

The 28-acre estate with an opulent, spacious Colonial home and other out buildings, was the residence of Howard J. Dietz, heir to a lamp manufacturing fortune. The home boasted a heated four-car garage and a garden with a sprinkler system, big deals for the time. Dietz earned a reputation as a civic leader and aviator. When Dietz died in May 1922, his executors sold the estate to a religious order of nuns. But apparently before the order took over, smuggler Rudolph Wylk used the estate to hide liquor smuggled in from Rum Row. Authorities found some $300,000 worth of liquor in a barn at the estate in March 1929.

5) Frank Costello's home in Sands Point

After Prohibition in 1944, the wealthy Costello purchased the home now known as 5 Barkers Point Road for $30,000. He lived there with his wife, Loretta, and attempted to fit in with his neighbors, one of whom was Newsday’s co-founder and editor Alicia Patterson. After Patterson had a chance meeting with Costello, she sent columnist Jack Altschul to interview the gangster. The result was a big spread in Newsday in June 1950, complete with photographs, in which Costello admitted he was a big gambler but brushed aside suggestions he had political clout with New York City politicians, sayings "I couldn’t even get a parking ticket fixed." The home, which has been extensively renovated, was sold after Costello’s death in February 1973 to satisfy his tax debts.

Frank Costello with his wife, Loretta, in front of their...

Frank Costello with his wife, Loretta, in front of their home in Sands Point on May 27, 1950. Credit: Newsday/Edna Murray

6) Rudolph Wylk residence in Rockville Centre

While not as famous as Frank Costello, Dutch Schultz, William "Big Bill" Dwyer and other bootleggers, Rudolph Wylk ran one of the biggest rum running operations on Long Island during Prohibition. Authorities believed his smuggling ring worked a territory which stretched from Montauk Point to South Carolina. Officials suspected Wylk paid for some of his operation in through a check swindle involving the First National Bank of Rockville Centre, a charge which was dismissed on a technicality. In March 1929, Wylk’s luck ran out when he and over a dozen other men were indicted on federal charges their syndicate used ships and trucks to bootleg several million dollars worth of booze a year, some of which was found at the old Dietz estate. In December 1929, Wylk was sentenced to two years in federal prison and fined $10,000 for his crimes. His residence was located at 80 Maple Ave. in Rockville Centre.

7) Greenport

Annie and Hans Fuhrmann lived in this North Fork town after their marriage in 1924 but things soon started to deteriorate in their relationship. Hans wanted to get some of the quick money to be made through bootlegging and would disappear for weeks on end as he crewed rum-running vessels, leaving Annie to fend for herself. When Hans returned from his sojourns, he was usually drunk and abusive to his wife.

Fed up, Annie decided to spill the beans to The Brooklyn Eagle, which ran a sensational series of articles about her allegations. Although the newspaper didn’t name names in print, more detailed information was given to federal authorities who used Annie’s tips to federal agents about her husband’s ties to bootlegging.

Hans ultimately decided to cooperate and prosecutors brought indictments against rum runners like William "Big Bill" Dwyer, Irving Wexler and Frank Costello. Dwyer and Wexler were convicted but Costello got a mistrial and was freed. Hans Fuhrmann eventually killed himself in a Manhattan hotel room although Annie believed that the mob had done him in.

8) Claudio’s Restaurant in Greenport

The town on Peconic Bay was a natural destination for run rummers after picking up cargo from Rum Row. They had plenty of places to offload, including Claudio’s Restaurant located at 111 Main St. Founded in 1870 by Manuel Claudio, a seaman on a whaler who fell in love with Greenport, Claudio’s became a popular eatery.

Several people pose with beer  outside Claudio's in Greenport on April...

Several people pose with beer  outside Claudio's in Greenport on April 7, 1933, despite the fact that Prohibition was still the law of the land at the time. Credit: Courtesy Mikayla Vielot

When Prohibition came, smugglers could bring their cargo through the pilings under the restaurant’s first floor and deliver liquor to the eatery through a trap door. The first floor served as a restaurant but on the second floor was a speakeasy. Part of the cargo could also be sold on a wholesale basis.

Claudio’s grew into a major seafood complex and was sold in 2018 after over 140 years with the Claudio family.

9) Bayville

In February 20, 1927, the schooner W.T. Bell ran aground off Bayville in strong winds with its cargo of over 200 kegs of whisky. Curious locals discovered the cargo and removed much of it before authorities arrived. The wreck was later dynamited by the Coast Guard. In separate incident the speedboat Alice Jane evaded Coast Guard in December and dumped case of booze over hoard onto an ice flow for later pickup.

10) Orient Point

The point is the most easterly location on the North Fork and thus was a place where rum runners could quickly land their cargoes after picking it up from the big cargo ships on Rum Row. In August the 1931, vessel Artemis rammed a Coast Guard vessel off that location and fled. Historian Jonathan Olly noted that the authorities eventually found the Artemis in Port Jefferson being repaired. After Prohibition, the Artemis under a different name became a ferry boat serving Fire Island.

The Orient Point Inn, a boarding house that opened in...

The Orient Point Inn, a boarding house that opened in 1796, is photographed circa 1950. Credit: Newsday/Courtesy of Oysterponds Historical Society

11) Hampton Bays

Credit: Flourish

This East End community was the site of a speakeasy in the Canoe Place Inn, not surprising given its convenient location for access to rum runners. In July 1930, federal authorities, as part of a wider investigation of radios being used to communicate with rum running vessels, located a secret radio receiver in the billiard room of what was described as the Horton Mansion. Two people were taken into custody, although one was released. Three other locations on Long Island were hit during a series of coordinated raids.

Canoe Place Inn in Hampton Bays in the 1920s. 

Canoe Place Inn in Hampton Bays in the 1920s.  Credit: Archival Postcard courtesy of the Southampton Historical Museum

12) Curtiss Field near Valley Stream

According to the Town of Hempstead website, the airfield opened in 1928 as Rogers Field, although court testimony indicated that Frank Costello had seaplanes fly out from the facility sometime before that date to rendezvous and guide rum running vessels along Rum Row. The airfield only stayed open as a commercial venture until 1933 but was used for other purposes through World War II. The Green Acres Mall opened in 1956 on the site of the airfield, the website reported.

13) Robins Island and Peconic Bay

This island has been in private hands since the 17th Century. Situated as it is in the middle of Peconic Bay, the island was a convenient spot for bootleggers to hide their loads of liquor to avoid confiscation by the Coast Guard.

14) Villa Carola, Sands Point

The address now known as one 1 Thayer Lane is the site of the old Isaac Guggenheim estate built in the style of an Italian villa in 1916. The structure and its surrounding gardens made it one of the great North Shore homes considered part of the Guilded Age. Guggenheim died in 1922 at the age of 68. Located facing Hempstead Bay, the estate was an ideal destination for bootleggers. In 1924, local Port Washington police caught a group of rum runners one night in the process of off loading hundreds of cases of liquor on the estate and arrested them. One of those arrested was Edward Aloise, a relative of Frank Costello. The estate is now home to the Village Club of Sands Point.

15) City of Long Beach

This city by the sea become one of the major rum running destinations of Long Island. Aided by some corrupt city officials—one story was that lights in a city clock tower signaled to bootleggers when it was okay to land their illicit cargo—the city was a friendly place for criminals like the notorious Irish gang leader Charles Higgins of Brooklyn. Court testimony indicated that Higgins ran some of the Long Beach rum runners. Police suspected Higgins was involved in several murders but were unable to make a case against him. One true crime author also speculated that Higgins played a role in the death of vivacious socialite Starr Faithfull, who was found dead on the beach off Mississippi Avenue in 1931. Federal officials tried to make a bootlegging case against Higgins and some of is Long Beach syndicate members but a jury acquitted them. In June 1932, Higgins’s luck ran out when he was gunned down and killed as he exited a Knights of Columbus building in Brooklyn.

The Nassau County Police Department confiscates illegal tills in Long Beach in...

The Nassau County Police Department confiscates illegal tills in Long Beach in 1932, during the waning years of Prohibition. Credit: Courtesy of Arcadia

16) Oyster Pond Beach

One mile north of Montauk Lighthouse, the location site of beaching of 110-foot rum runner vessel the Algie, stocked with liquor reportedly valued at $75,000. According to Prohibition historian Ellen Nickensie Lawson, the Algie had sailed for over a week from Nova Scotia and was tailed during that period by Coast Guard. The vessel actually ran aground just off shore on the Shagwond Reef, noted Lawson.

Horseback riders make their way along the narrow strip of...

Horseback riders make their way along the narrow strip of beach that separates Block Island Sound from Oyster Pond. Credit: Newsday/John Paraskevas

17) Jones Inlet (Long Beach island)

It was no surprise given its location near Long Beach that the inlet on the eastern tip of the island saw a great deal of rum runner nautical traffic. The Coast Guard was wise to that fact and during the investigation of Rudolph Wylk seized his vessel the Mary Mother Elizabeth. The vessel was supposedly named after the Mother Superior of Mercy Hospital who was a family friend. Wylk also operated vessels off Debs Inlet, which was further west on Long Beach island.

The view looking east at the barrier beach stretching off...

The view looking east at the barrier beach stretching off into the far distance, as seen from Jones Inlet. Credit: NEWSDAY STAFF/Ken Spencer

18) Huntington Bay

Located on the North Shore, the bay was a favorite port of call for rum runners who worked the Long Island Sound route. Historian Ellen Nickenzie Lawson uncovered documents which spelled out the curious voyage of an Italian schooner Arco Felice crewed by a group of Sicilian men out of the town of Castellamare del Golfo, Sicily. The schooner was seized by authorities and although no liquor was found, the deck was strewn with bottle corks. The manifest, according to Lawson, showed that the vessel had picked up 8,000 cases of whiskey and champagne in Havana, Cuba. Some of the crew were sentenced to terms in federal prison even though there was only circumstantial evidence against them—the manifest and the corks. The defendants were ultimately released after an appeals court ruled it wasn’t a crime to sell or deliver liquor on the high seas.

 A bottle of whiskey in a shadow box hangs at...

 A bottle of whiskey in a shadow box hangs at Finnegan's Restaurant and Tap Room in Huntington in June 2011. Credit: Newsday/Karen Wiles Stabile

19) Wreck of the Lizzie D., about four miles south of Freeport inlet

The 85-foot tug Lizzie D was used as a rum runner until October 1922 when it was lost at sea with all of its crew of about a dozen souls. It had sailed from New York Harbor on October 22, reportedly to tow a barge, with only a day’s supply of food for the crew. While reports had the vessel spotted west of Fire Island, its remains were never found until 1977. The wreck has attracted divers over the years, notably Steve Bielenda of Miller Place. On numerous dives Bielenda recovered intact bottles of whiskey which retained their amber hue largely but were undrinkable because of contamination. Bielenda also recovered parts of the wooden liquor cases. Another poignant recovery by Bielenda were some shoes, presumably those of the lost crew members. There were a number of other misadventures which took the lives of rum runners. One of the most infamous was the sinking of the William P. Maloney with all 12 crewmen in November 1924. Officials believed Manhattan bootlegger William Dwyer used the vessel for smuggling liquor even though it was unseaworthy. The tragedy of the William P. Maloney left a number of widows and 22 children without their fathers.

20) Mattituck

This North Shore hamlet was site of another 1930 secret radio transmitting raid on estate of prominent businessman Joseph Wichert. Federal agents raided the home while a dinner party was underway with the guests in formal dress. According to a news report about the raid, the agents waited until the last dinner course was served and cigars were being smoked before they served Wichert with an arrest warrant on charges of conspiracy to violate Prohibition. Officials didn’t find any transmitter on the property but technicians said they had traced signals to the location a few days earlier.

21) Quogue

As part of the same series of 1930 raids on homes in Mattituck, federal agents found a transmitter in a house in Quogue. Agents found a man seated at the telegraph sending a message to what was described as a "undetermined destination."

A man walks his dogs along the beach in Quogue...

A man walks his dogs along the beach in Quogue in October 2018. Credit: James Carbone

22) Southampton

A fourth location hit in the 1930 radio raids occurred at what was identified in news accounts as the old Howard homestead where agents found another radio transmitter. Three men were arrested during the raid.

A couple strolls along Coopers Beach in Southampton in January 2021.

A couple strolls along Coopers Beach in Southampton in January 2021. Credit: John Roca

23) Great Neck

Site of the fictional estate of Jay Gatsby in F. Scott Fitzgerald’s The Great Gatsby, the great American novel about the Roaring Twenties. The area was known in the novel as "West Egg" and Gatsby’s estate faced Manhasset Bay which divided the community from "East Egg," which is in reality the peninsula occupied by Sands Point. In the story, Gatsby made his money by working as a bootlegger and appeared to have been involved in a financial swindle.

Sources: Archival newspaper reports, Smugglers, Bootleggers, and Scofflaws: Prohibition and New York City, by Ellen NicKenzie Lawson, Last Call: The Rise and Fall of Prohibition by Daniel Okrent, "The Wreck of the Rum-Runner W T Bell," article by Daniel E. Russell, city historian, City of Glen Cove, The Long Island History Journal, The Long Island History Museum, Port Washington Public Library