This Day in History: Benjamin Tallmadge's Raid

On this day in 1780, a force led by Benjamin Tallmadge silently crosses the Long Island Sound. You might know Tallmadge for his association with the Culper Spy Ring, but on this occasion, he was on a different sort of mission: George Washington had authorized him to attack a British fort.

The attack came mere weeks after Benedict Arnold’s treason, and Tallmadge would write that “my former scheme of annoying the enemy on Long Island came fresh upon my mind” in the wake of Arnold’s treachery.

He began gathering information about a British fort being constructed on the southern shore of Long Island. He even crossed the Sound to personally investigate. “Among other things,” he later wrote, “I learned that [the fort] was completed—that it was the depository of stores, dry goods, groceries, and arms . . . .”

He also learned that the British had stockpiled hay nearby.

Armed with this information, he wrote Washington. “If your Excellency wishes to have the hay destroyed, or the Corps taken,” he wrote, “I don’t doubt of its practicability, & with about 40 or 50 of our dismounted Dragoons, I would undertake it.”

Washington agreed.

Thus it was that Tallmadge and 80 dismounted dragoons met at Fairfield, Connecticut, on November 18. The weather was terrible, but they had eight boats ready to carry them across the Sound when it improved. Finally, on the evening of November 21, they were able to get across.

Once across, bad weather stalled them—again! But on November 22, they finally began their march toward the fort.

“[T]he Works of Fort St George,” Tallmadge later reported, “consisted of two large strong Houses, and a fort about 90 feet square, the whole connected together by a very strong Stockade . . . forming a compleat Triangle, & the Fort & Houses standing in the extrimities of the Angles. The fort consisted of a high Wall & a deep Ditch, encircled with a strong Abbatis, having but one Gate . . . .”

Intelligence told him that about 50 enemy soldiers were inside.

Tallmadge split his force into three, so he could attack from all sides. He would lead the first detachment. The other two were to stay concealed until he’d been fired upon.

The attack began at dawn on November 23. Tallmadge’s group was within 40 yards of the fort when it was first spotted.

“At this moment,” Tallmadge wrote in his memoirs, “the sentinel in advance of the stockade, halted his march, looked attentively at our column, and demanded, ‘Who comes there?’ and fired. Before the smoke from his gun had cleared his vision, my sergeant, who marched by my side, reached him with his bayonet, and prostrated him.” 

The other two detachments joined the fight. Would you believe that the dragoons took the fort within only 10 minutes? Apparently, they were yelling “Washington and glory!” as they basked in victory.

They celebrated a tiny bit too soon.

Just then, musket fire came from one of the houses: Some of the British had barricaded themselves in. Naturally, Tallmadge and his dragoons made short work of that, capturing the British inside. As if all that weren’t enough, they soon captured a ship they spotted just off the coast, too!

Tallmadge set fire to the boat and fort, then he and his dragoons marched back the way they came, taking supplies and prisoners with them. They had not lost a single man.

The raid was one of the smaller victories in the American Revolution, of course, yet it served its own purpose, forcing the British to allocate more resources to holding Long Island than they might have otherwise.

Did Washington’s army benefit from that later as it moved south, away from New York? Potentially.

Less than a year later, Washington would win his decisive victory at Yorktown.

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Primary Sources:

• Benjamin Tallmadge, Memoir of Col. Benjamin Tallmadge, prepared by himself, at the request of his children (1858)

• Letter from Benjamin Tallmadge to George Washington (Nov. 7, 1780)

• Letter from Benjamin Tallmadge to George Washington (Nov. 24, 1780)

• Letter from Benjamin Tallmadge to George Washington (Nov. 25, 1780)

• Letter from George Washington to Benjamin Tallmadge (Nov. 11, 1780) (reprinted FN 7 HERE)

• Sarah Friedman, Major Benjamin Tallmadge and the Battle of Fort St. George (Journal of the American Revolution; Nov. 9, 2020)

• Suffolk County, NY  |  Nov 23, 1780 (American Battlefields Trust)