January 17, 1920, marked the beginning of Prohibition. One of its purposes had been to improve morals in society by eliminating alcohol. But within weeks, the continued demand for illegal spirits soon led to smuggling and organized crime. Long Island Sound, with its 600 miles of coastline and the south side of Long Island are marked by inlets and secluded coves. They provided great opportunities for rum-runners, making them the major source of New York City’s illegal alcohol.
Smuggling hooch could be big money for anyone involved. Larger vessels usually headed offshore at night, just beyond the 3-mile limit of U.S. territorial waters. Once there, they rendezvoused with “mother ships.” From the site called Rum Row, the vessels then headed toward the coast to meet up with smaller boats that transported their treasure to shore. Some fishermen and baymen were involved in the final transport. British whiskey shipped to the Bahamas, other Caribbean destinations and the French island of Saint Pierre and Miquelon were part of the supply route. Rum originated from the Caribbean, while Canadian distilled whiskey often made its way from Nova Scotia. Once ashore, trucks with false bottoms, sometimes disguised as carriers of newspapers or bakery goods, made their way to New York City’s speakeasies. The city eventually had more than 30,000 speakeasies.
Early on during Prohibition, enforcement of its laws on land and sea was primarily conducted by state law officers and federal agents. They were mainly engaged in apprehending smugglers as they unloaded their goods at wharves or capturing small craft inshore. But in 1923, the U. S. Coast Guard was given the task of enforcing the laws at sea. At the time, however, they were ill-equipped with only 75 vessels compared to the more than 240 rum-running vessels! Some smugglers had boats equipped with aircraft engines that could attain speeds of 40 mph!
The Coast Guard was soon able to get Congress to extend U.S. territorial waters out to 12 miles. Funds were appropriated for pursuit boats to accommodate the vessel needs of the Coast Guard. In addition, they were provided with reconditioned Navy World War l destroyers that could attain a speed of 33 mph, but they were restricted from inshore waters due to their deep draft. Around 1925, the Guard was also provided with 5 amphibious planes for aerial patrol. They were stationed at Gloucester Harbor. By the 1930s, the Guard used direction-finding equipment to track radio signals between rumrunners. They were also able to decode their intercepted radio communications.
During Prohibition, Long Island, nicknamed “Liquor Island,” and the Sound became a major hub for bootlegging and smuggling. Nearly one-third of the illegal liquor that made its way to New York City came from their inlets and coves.
In the early morning hours of February 20, 1927, bitter winter winds blowing out of the northeast gusted up to 70 miles per hour. The lumber schooner W T Bell, converted to a rum-runner, was carrying $500,000 worth of scotch and whiskey, loaded in barrels. As they headed for Glen Cove, Long Island, the storm’s massive waves swept the two-masted schooner ashore at Bayville’s Oak Neck Point. Continually battered by heavy surf, the crew realized that they needed help getting safely ashore. Signaling for help, a Bayville resident quickly responded. Using a Lyle gun, the crew was able to shoot a line out to the resident, who then secured it on a beach boulder. He then headed back to town to get additional help. Arriving with members of the local fire department, a bosun’s chair was set up, resulting in all 6 of the crewmen being successfully evacuated. The crewmen were then taken to a nearby estate where they were provided with food, drink and dry clothes. But soon after, the men declared that they needed to go back to the beach to check on the shipwreck.
When the crewmen didn’t return to the estate, a group of local citizens headed to the wreck site and found that the men had all disappeared. On inspection of the schooner, they quickly realized why the crew had run off. The abandoned schooner was filled with barrels of alcohol carrying the inscription “Blended Whiskey, Newfoundland.” It was a gift from the sea! Bayville residents immediately began tossing the barrels over the ship’s side, while men on the beach waded out into the cold waters to drag them in. Barrels that floated away were retrieved using rowboats. It was a “free-for-all.” As the word got out, more residents joined in, along with some bootleggers from nearby Oyster Bay. It is estimated that about 125 barrels had been retrieved before local authorities arrived on the scene to put a stop to the activity. A month later, fearing that W T Bell might pose a navigational hazard if it refloated during a storm, the Coast Guard dynamited its remains.
Because of its proximity to New York City, Glen Cove was a popular drop-off point for illegal liquor. However, many other harbors and sites were used throughout Long Island Sound. Montauk, with its numerous coves and harbors and its short distance from Rum Row, worked well for smugglers. Greenport and Southold, just west of Orient Point, were popular delivery sites. Many of the area’s farmers, fishermen and other residents stored the booze in their barns, garages or sheds for later transport. At night, trucks loaded with spirits headed for New York. Greenport’s Claudio’s Tavern and Grill was partially built over water. It allowed bootleggers to run their boat directly under the restaurant and pass their goods up through a trap door. Located behind the bar, “the trap door still exists today.”
The Coast Guard encountered a wide variety of rum-running vessels in the vicinity of Montauk. When they stopped and searched the yacht Surf, a former World War l American Red Cross vessel, they found that it was carrying 4,000 cases of whiskey. In another incident, around midnight in August 1931, the Coast Guard spotted the 52-foot Artemis. Equipped with 3 Liberty engines, the boat could attain a speed of 52 mph! When ordered to stop, the run-runner quickly altered course and headed away. The Guard then fired their machine gun, wounding two of its crewmen. At that point, the Artemis turned once more and rammed the cutter. Also damaged, the rum-runner landed in a cove near Orient Point, where two of the wounded crewmen were transported to a Greenport hospital. At the same time, the remaining crew unloaded their booze with the enthusiastic aid of local citizens. Artemis was then towed to Port Jefferson boatyard by the vessel Evangeline. Following repairs, the rum-runner managed to leave Port Jefferson and return to its law-breaking career. However, at the end of Prohibition, the ship was converted into a ferry that ran between Bay Shore and Fire Island.
Coastal Connecticut, from Stonington to Greenwich, also provided multiple destinations for rum-runner deliveries. Old Saybrook’s Electric Trolley Powerhouse, located at the mouth of the Connecticut River, served as a prime drop-off site. Cornfield Point’s Ye Castle Inn became a popular location that provided gambling along with illegal alcohol for the rich. August Strusholm, married to one of the inn’s owners, developed one of coastal Connecticut’s largest smuggling operations. By the mid-1920s, he had five cruisers equipped with Liberty aircraft engines that could easily outrun Coast Guard vessels. He also enlisted local commercial fishermen, directing them to go out to the territorial waters to pick up booze. Once back on the coast, some trucks transporting the goods were disguised with a caption painted on their side: “Hartford Laundry or Hellman’s Mayonnaise Delivery Service.” A great deal of the illegal alcohol made it to Hartford’s speakeasies and other state sites. In February 1924, law enforcement officials invaded Hartford’s Front Street garage, where they discovered a chamber filled with hundreds of gallons of booze. It was said to have been the “biggest haul in city history.”
During Prohibition, there were many other rum-running incidents on both sides of the Sound: shipwrecks, loss of life, the flourishing of organized crime and capture of smugglers by authorities. Near New York City, approximately 250 rum-running ships were seized, but it was obvious that the thirteen years of Prohibition had been a total failure. On December 5, 1933, the 21st Amendment repealed the legalization of national Prohibition.