In 1781, George Washington and Benjamin Tallmadge discussed the feasibility of launching a daring raid across the Long Island Sound. Part of the correspondence now resides in the Washington Library at Mount Vernon.

George Washington needed a victory.  From George Washington to Benjamin Tallmadge, 8 April 1781 - Gift of Alexander B. Trevor, direct descendant of Benjamin Tallmadge, 2015.The American War of Independence was in its seventh year.  The main army had not fought a battle since 1779, and the British decimated the Southern Army in a string of defeats at Savannah, Charleston, and Camden.  Georgia and South Carolina’s state governments had fallen to the British, North Carolina’s was on the run, and the arch-traitor himself, Benedict Arnold, had descended on Washington’s native Virginia.  The Fred W. Smith National Library’s latest document acquisition details  what Washington had in mind for a response to these dark times.

From behind the West Point fortifications in April of 1781, Washington contemplated a daring raid that, if successful, would rate alongside Trenton, Princeton, and Stony Point in the annals of American military history.  “The success of the Enterprise,” Washington wrote to his chief spymaster Colonel Benjamin Tallmadge, “must depend, on … the secrecy of the attempt, and a knowledge of the exact situation of the enemy.”1  The plan Tallmadge and Washington drew up contemplated a daring cross-channel raid by Franco-American forces against a Long Island Loyalist stronghold and involved the most famous spy-ring of the war.  

Since 1778, the main British and American armies had settled into the greater New York City area ensconced behind their respective fortifications on Manhattan and in the Hudson Highlands.  The stalemate created a “no man’s land” in Westchester County, New York and portions of western Connecticut as sympathizers of both sides bushwhacked each other.2  The area was rife with intrigue and espionage; and a major source of supplies for Crown forces in the region came from Fort Franklin on Lloyd’s Neck, Long Island.3

 

Lloyd’s Neck is roughly two miles across and connected to Long Island by a narrow isthmus.  From it’s heights, Fort Franklin, named after Benjamin Franklin’s Tory son William Franklin, commanded Oyster Bay and  sheltered Tory whaleboats that supplied Loyalists on the mainland.  The fort and it’s boats had long been a thorn in Tallmadge’s side and hindered his mission of suppressing Tory sympathies in the region.4  Those sympathizers would harm any major assault on New York City, Washington’s primary goal for the 1781 campaign season.5  If Tallmadge could destroy Fort Franklin, the Continental Army near West Point, and the French Army in Newport, Rhode Island, would be that much closer to capturing New York, and hopefully ending the war. 

Despite often being referred to as "Fortress West Point," the military post actually consisted of a number of small forts and redoubts advantageously posted around a strategic bend in the Hudson River. - Plan de West-Point du nord, levé a vue, [1780]. Courtesy Library of Congress [G3804.W53S3 178- .P5]Unfortunately for Washington, directly supporting Tallmadge’s raid would be problematic. “Moving troops towards the [Long Island]  Sound,” the general wrote “would give such indications of the design as would effectually frustrate the success”6 precisely because of the very Crown supporters that Tallmadge sought to reduce aid too.  Continental Army soldiers would have to pass through enemy territory just to get into position to conduct the raid.  Accordingly, Tallmadge would “be at the liberty, to be the bearer of the enclosed Letter to His Excellency the Count De Rochambeau.”7  Amphibious French troops based out of Rhode Island would be in a much better position to strike rapidly against the Loyalist-held fort without warning, and Washington whole-heartedly advised his subordinate to seek out the assistance of their allies to the east.

This map, contained in the Rochambeau Map Collection at the Library of Congress highlights Tallmadge's success in completing the reconnaissance mission George Washington assigned to him. - Map of Queens Village or Lloyd Neck. [1781] Courtesy Library of Congress, [G3802.L5 1781 .M3].Tallmadge continued to gather intelligence about Fort Franklin by corresponding with Abraham Woodhull of the famed Culpepper spy ring.8  Tallmadge even ventured across to Long Island himself as a spy to verify the latest information; no small feet given he had been present at the American execution of British officer John Andre less than a year earlier for just such an offense.9  Tallmadge then traveled to Newport to meet with the French and share his information.  Rochambeau, by Tallmadge’s account, delighted in the daring American officer’s presence and informed him of the glowing letter of introduction Washington had written.10

Unfortunately for Tallmadge’s plans, the French had no ships to spare for such a raid.11  A major portion of the British Royal Navy had returned recently to New York harbor following the Battle of Cape Henry and the transport of roughly 2,000 additional Crown soldiers to Virginia.12  This reinforcement to northern waters necessitated defensive patrols by the French and increased the chance that the British would have too sizable a force of their own patrolling Long Island Sound.

While the news that Tallmadge could not undertake the raid surely frustrated Washington, the information provided by the Long Island spies nonetheless led to Washington’s greatest victory of the war.  The deployment of 2,000 additional troops to Virginia and the tepid behavior of the Royal Navy’s officers encouraged the Franco-American armies to look to the South for their war-wining victory rather than to New York City.13  By September, only four months after Washington informed Tallmadge he could not send any troops south to Long Island, Washington was leading both the Continental and French Army’s south to Virginia, and to victory at Yorktown.

 Joseph F. Stoltz III, Ph.D.

Digital Historian
Fred W. Smith National Library for the
Study of George Washington at Mount Vernon

Notes:

1. George Washington to Benjamin Tallmadge, April 8, 1781, Fred W. Smith National Library for the Study of George Washington at Mount Vernon, Mount Vernon, VA.
2. Benjamin Tallmadge, Memoir of Col. Benjamin Tallmadge, Prepared by Himself, at the Request of his Children (New York: Thomas Holman, Book and Job Printer, 1858) 33-34, 38-39; Mark V. Kwansy, Washington’s Partisan War, 1775-1783 (Kent: Kent State University Press, 1996) 284-285.
3. Benjamin Tallmadge to George Washington, April 6, 1781, George Washington Papers at the Library of Congress, 1741-1799: Series 4. General Correspondence, 1696-1799, Library of Congress, Washington, DC.
4. Tallmadge had also attempted to raid Fort Franklin the previous year in 1780.  Hampered by the uncooperative American general William Heath and a well prepared Royal Navy, Tallmadge succeeded only at destroying the smaller Fort Slongo, east of Fort Franklin. Benjamin Tallmadge, Memoir of Col. Benjamin Tallmadge, Prepared by Himself, at the Request of his Children (New York: Thomas Holman, Book and Job Printer, 1858) 39-42.
5. Conference with Comte De Rochambeau, The Writings of George Washington from the Original Manuscript Sources, 1745-1799, vol. 22, ed. John C. Fitzpatrick (United States Government Printing Office: Washington, 1937) 105-107; Jean-Baptiste-Donation de Vimeur Comte de Rochambeau, Memoirs of the Marshal Count de Rochambeau Relative to the War of Independence in the United States (Paris: Belin and Co,1838) 42-43, 45.
6. George Washington to Benjamin Tallmadge, April 8, 1781, Fred W. Smith National Library for the Study of George Washington at Mount Vernon, Mount Vernon, VA.
7. Ibid.
8. Benjamin Tallmadge to George Washington, April 20, 1781, George Washington Papers at the Library of Congress, 1741-1799: Series 4. General Correspondence, 1696-1799, Library of Congress, Washington, DC.
9. Ibid; Benjamin Tallmadge, Memoir of Col. Benjamin Tallmadge, Prepared by Himself, at the Request of his Children (New York: Thomas Holman, Book and Job Printer,1858) 37-39, 43.
10. Benjamin Tallmadge, Memoir of Col. Benjamin Tallmadge, Prepared by Himself, at the Request of his Children (New York: Thomas Holman, Book and Job Printer,1858) 43.
11. Benjamin Tallmadge to George Washington, April 24, 1781, George Washington Papers at the Library of Congress, 1741-1799: Series 4. General Correspondence, 1696-1799, Library of Congress, Washington, DC.
12. John Ferling, Almost a Miracle: The American Victory in the War of Independence (Oxford: Oxford University Press, 2007) 502-503.
13. Edward G. Lengel. General George Washington: A Military Life (New York: Random House Press, 2005) 333-335.
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