On the morning of May 23, 1777, 170 soldiers from several regiments of the American Continental Army crossed Long Island Sound from Guilford, Connecticut, in 13 whaleboats.
By approximately 6 p.m., they were on the beach at the north end of Hashamomuck Pond, what today is Southold’s Town Beach. They portaged their whaleboats over the beach and slipped into the pond, then rowed its length to the point where it empties into Peconic Bay and passed Shelter Island.
What would later be known as Meigs Raid, or the Battle of Sag Harbor, was underway.
That year, after George Washington’s army was routed in the Battle of Long Island — which was essentially fought in Brooklyn Heights in August 1776 — all of Long Island and Manhattan Island were under British occupation.
As was true throughout the Northeast, Long Island was divided between Patriots who wanted to expel the British and form their own government, and pro-British Loyalists who wanted to remain in the empire. Families split into factions over the question of loyalty versus armed revolution.
The residents of the North Fork, Shelter Isalnd and South Fork towns predominantly favored revolution.
To the British, Long Island was a breadbasket from which they could feed their army. To that end, British troops were bivouacked in many places, where they made their presence felt by foraging for wheat, firewood, cattle and food crops and extracting loyalty oaths from the local population.
In Southold — Riverhead Town did not exist until 1797 — British troops were camped in various places, including the west side of Marratooka Pond in Mattituck, said Southold Town historian Amy Folk.
British sailing vessels were anchored in Gardiners Bay, in Sag Harbor and off Shelter Island, which was then home to the vast Sylvester Manor plantation, and rich in crops.
A Southold history by former town historian Antonia Booth states that approximately 500 infantry and 50 cavalry occupied the town for four years. “The British closed churches, plundered horses and grain and even dug up gold and silver buried by those who left …” she wrote.
“Trees were cut down for fuel to keep British officers in New York warm throughout the long occupation,” she wrote. “When Patriot funds ran out in New England, those who had left for the mainland lived in poverty, while those who stayed behind suffered even more.”
The Revolution “tore families apart,” Ms. Folk said. “One part of the family stayed with the British, and if that side won they would come out ahead; the other part would come out ahead if the Patriots won.”
There was an American-built fort at Orient Point overlooking Plum Gut, Ms. Folk said, but after the Battle of Long Island its guns were removed and taken to Connecticut. The British then took over the fort.
After the loss in Brooklyn, East End residents who were not loyal to the British were told to evacuate to Connecticut, Ms. Folk said. “So many people and families abandoned their homes and their farms and moved away, while others stayed behind,” she said.
“But if you stay, the Patriot forces consider you a Loyalist,” she added. “There is open season on anyone who stays … And then the British begin foraging operations. They take food, grain, meat, wood, everything they need … The governor of New York, William Tryon, became a general in the British Army, and he lived in Mattituck for a while.”
”The Wickham family in Cutchogue was split between Patriots and Loyalists. The head of the family, Parker Wickham, was at one point kidnapped by Patriots and removed to Connecticut. After the Revolution, the new state of New York punished Mr. Wickham by confiscating hundreds of acres his family owned in Cutchogue.
Centuries later — in the 1980s — descendant John Wickham sued New York State in an effort to reclaim one part of the family’s former holdings, Robins Island.
“In many ways, the Revolution was a civil war,” said Neil Buffett, assistant professor of history at Suffolk County Community College. “These were English colonists here. We spoke English. We shared a political and material culture. When we broke away, it was essentially a civil war within the English world and within families.”
The Meigs Raid was the only battle of the Revolution that occurred on the East End. After forces commanded by Return Jonathan Meigs reached Peconic Bay, they navigated around Shelter Island to Sag Harbor, where a British force was engaged in foraging operations.
The Patriots landed in Sag Harbor on the morning of May 24,1777, destroying Loyalist property. Casualties were all on the Loyalist side, with nearly 100 captured, as both sides fought on Meeting House Hill in the village, which was fortified with earthworks.
Meanwhile, a second group of the Patriot forces destroyed a number of British boats in the harbor. Captured Loyalists were taken back to Connecticut after the raid.
After the war, some North Fork and Shelter Island residents who had fled returned from Connecticut. Some lost farms that had been in their families since the 1600s.
“Decades of penury followed,” Ms. Booth wrote, as cash was scarce and those who had been gone for seven years found it impossible to restart their lives on land they once owned.