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This Day in History: The Culper Spy Ring, Benjamin Tallmadge & a raid on Lloyd’s Neck

On this day in 1779, Benjamin Tallmadge leads a raid on Lloyd’s Neck. You may know Tallmadge as the leader of George Washington’s Culper Spy Ring, but did you know that there was a more traditional military side to him, too?


Tallmadge was an officer in the Continental Army. He was also a native of Long Island.


Understandably, this Long Island native was disturbed by much of what was going on in that area during the American Revolution. New York was the British headquarters during the war, and the areas around it suffered accordingly.

A 1790 portrait of Tallmadge with his son

For one thing, the area was full of raiders! The shores of Long Island, Connecticut, and New Jersey all suffered as Loyalists raided the homes of Patriots. To be fair, sometimes Patriots raided Loyalist homes, too. Whaleboating crews were a particular problem.  They could maneuver in and out of shallow areas, striking quickly and evading attack.


On the Loyalist side, the whaleboaters received protection from a British fort on the north side of Long Island. Fort Franklin was built on Lloyd’s Neck, a thin peninsula jutting out into Long Island Sound. The fort was named for Benjamin Franklin’s son, who was a Loyalist.


The fort was difficult to defeat. It stood atop a high bluff, and it was manned by hundreds of soldiers at any given point in time.


In 1779, Fort Franklin and the other British garrisons along Long Island Sound became important to the British for another reason: They became a springboard for military raids into Connecticut. General William Tryon used these forts when he raided New Haven, Fairfield, and Norwalk.


All in all, it was a terrible situation. The raiders, Tallmadge wrote to Washington, “conduct most villanously towards the Inhabitants of Long Island, by lying on the Roads & robbing the Inhabitants as they pass. . . . [They] land on L. Island & plunder the Inhabitants promiscuously.”


During the summer of 1779, Washington and several of his officers discussed the prospect of a raid on Fort Franklin. In September, Tallmadge finally undertook the task.  His plan was two-fold: First, he would attack the Loyalist encampments at the base of the fort. These camps provided protection for the Loyalist whaleboat crews and other raiders. If he could take the camps quietly, then he would be able to sneak up on the Fort and launch a surprise attack.


Tallmadge launched his attack late on September 5.   He and about 130 men crossed Long Island Sound from Connecticut, landing quietly at Lloyd’s Neck.  Tallmadge later reported that the “large band of marauders” never saw him coming, and Tallmadge took the encampment without losing a single man.

“Our attack was so sudden and unexpected,” Tallmadge wrote, “that we succeeded in capturing almost the whole party—a few only escaping into the bushes, from whence they commenced firing on my detachment, which gave the alarm to the garrison.”


Tallmadge’s opportunity for a surprise attack on Fort Franklin was gone. He decided to abandon the second phase of his plan.  Instead, the Patriots burned the encampment, destroyed the boats, and took their prisoners back across to Connecticut.


Tallmadge had won a victory, but he’d failed in his ultimate goal of taking Fort Franklin. Unfortunately, it was a goal that would remain elusive throughout the Revolution.


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