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Dan Rattiner’s Stories

Gunfights in the Hamptons

By Dan Rattiner
8 minute 09/20/2025 Share
Counterfeiting service cartoon by Dan Rattiner
Cartoon by Dan Rattiner

The first gunfight in which shots were fired in the Hamptons came during the American Revolution that founded our country. After the British redcoats had handily defeated the rebels in the Battle of Brooklyn, all of Long Island suffered an occupation by the victors. Most of the young men who had fought and lost in Brooklyn had fled to Connecticut, where the rebels were still in charge. Those who remained, farmers and fishermen and their wives, mostly elders, had to sign loyalty oaths to the king. The redcoats were everywhere.

In the dark of night on May 24, 1777, a group of 226 rebels boarded small whaleboats in Guilford, Connecticut, and sailed across Long Island Sound so that, at 1 in the morning, they could pull the boats up on the sand in Noyac. They then walked the two miles to Long Wharf to surprise about 100 British redcoats who were guarding the warehouses there in which supplies brought ashore from England to feed, clothe and provide ammunition to the British soldiers on the Island were stored.

The British were asleep in their tents when the rebels came. In less than 10 minutes, after six of the redcoats who engaged in a gunfight were killed, the rest surrendered. The rebels walked their prisoners, all 96 of them, back to the whaleboats and sailed with them back across Long Island Sound to jails near Guilford.

This nighttime raid served notice on the British that the rebels were still around and might strike again with more surprises. This encounter is called Meig’s Raid, after the American who led it, Col. Return Jonathan Meigs.

The second gunfight in the Hamptons took place a generation later, long after the revolution was over, the United States was founded, and it was not quite clear what the new relationship between this country and the Crown might be.

It was 1812. James Madison was the president of the United States, and he reacted in anger when he learned that sailors aboard British warships in the Atlantic Ocean were boarding American freighters, kidnapping American crewmen and impressing them into the British Navy to become British sailors against their will. This would not be tolerated.

At the time, Madison did not have naval vessels that could defeat the British men-o-war, so his sabre-rattling was not going to amount to much. Nevertheless, the King of England decided to teach America a lesson. He ordered his British Men-o-War to cross the Atlantic, bombard America’s port cities, and row redcoats ashore to burn the ports to the ground before withdrawing.

One such order caused four British men-o-war to drop anchor off Sag Harbor. Rebels serving as sentries stationed along the shoreline saw them, because this was not long after the British came ashore at Baltimore, marched to the White House and set that on fire. (Madison and his wife, warned the Brits were coming, fled, leaving that morning’s breakfast on the table). Here at Sag Harbor, the sentries sounded the alarm.

Men from the militias in the Hamptons, learning the British were offshore, rode to Sag Harbor, evacuated the women and children, then climbed the big hill to the cannon overlooking Long Wharf for the upcoming battle, which took place the next night.

In that action, the redcoats landed on Long Wharf, overwhelmed the sentries and set fire to the boats there. They had no way to stop the steady fire of the big cannon atop the hill, however. As a result, though the redcoats fired back, they considered themselves outgunned, climbed back into their boats and rowed out to the men-o-war, satisfied, at least, with having burned the boats. They never came back.

One young American woman, declining to be evacuated, sat out the battle in her home and wrote an account of it. One of her entries, available to read at the library, describes “British cannonballs bouncing up Main Street.” It’s quite a document.

A brass historic marker is bolted to a giant boulder at the top of this hill where the cannon once sat.

If these set-piece battles took place to preserve our freedom, the next gun battle was all about money. It took place in the dark hours of 2 to 4 in the morning on May 24, 1924. Prohibition was in effect, and in Montauk, local fishermen were loading cases of liquor from European freighters into their boats and taking them to shore to hiding places until American bootleggers could bring out trucks, load them up and drive them to bars and speakeasies in New York City.

That night, a group of five Long Islanders, one of whom was a revenue agent, got into a gun fight with the locals at Montauk’s Deep Hollow Ranch where more than a million dollars worth of liquor were stored and guarded by the local fishermen.

Two men were wounded, and the next day when the sun rose, other revenue agents came with crowbars and axes to bash the alcohol bottles and cases to bits, ruining everything. A subsequent trial exonerated the fishermen who shot two of the visitors, while later on another trial exonerated those who fired at the fishermen in return before retreating. The battle made national news.

The fourth and last time shots were exchanged was on a foggy night on June 12, 1942 when four Nazi saboteurs in a rubber boat, launched from a German submarine just off Atlantic Avenue Beach in Amagansett, came ashore in front of the Amagansett Coast Guard Station there. The Americans were expecting such a thing. A coastguardsman walking the beach with a flashlight came upon them, accepted a $260 cash bribe from the lead saboteur, ran to the station, rousted his mates and, all bearing 30-year-old Springfield rifles, returned to the beach where they discovered the saboteurs gone, explosives in wooden crates  buried hurriedly in the sand, and the submarine stuck on a sandbar, its captain desperately trying to pull it off.

An Army unit biv-ou-acked in tents nearby showed up and, along with the coastguardsmen, fired shots at the sub, which some said later they saw returning fire. But the sub soon got off the bar and roared off.

Two weeks later, while in Manhattan, after some disagreements became apparent, one turned the others in to the FBI.

Four known gunfights in 400 years. It’s a good record for a peaceful, lovely place such as this. But none would have been even better.

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