Soldier Spy


Although the United States ultimately triumphed in the American Revolution, there were many dark chapters in the long and bitter struggle before final victory was achieved. One of the bleakest came in late fall 1776 as George Washington and the Continental Army fought to keep New York City out of British hands. Heavy fighting raged across Long Island and Manhattan as Washington contested the British advance, but by mid-November, the British had driven him off Manhattan island altogether, ensuring New York City remained under British occupation for the remainder of the war. Despite never regaining control of the city until after the British departed in December 1783, General Washington continually sought to drive out the British invaders. It was a desire steadfastly shared by another young Continental officer as well. Hailing from Long Island himself, the officer was particularly zealous in his desire to liberate the island from British oppression. Though his renown largely resulted from his role as Washington’s chief spymaster, he also proved himself a fierce guerrilla fighter. His name was Benjamin Tallmadge. This is the story of how he relentlessly led raids on the British garrisons across Long Island during the final years of the American Revolution.

Despite coming from an area later known for its staunch loyalty to the Crown, Benjamin Tallmadge was fully committed to the ideals of the Revolution. He was born in Setauket, Long Island in late February 1754 to the town’s Presbyterian minister. As a young boy, he acquired an abiding love for liberty and self-government, and his convictions deepened after he entered Yale in 1769 and befriended fellow patriot Nathan Hale. After graduating in 1773, Tallmadge moved to Wethersfield, Connecticut to teach school. There he was caught up in the uproar erupting over Parliament’s passage of the “Intolerable Acts,” which closed Boston Harbor and imposed martial law on Massachusetts in retaliation for the December 1773 Boston Tea Party. Along with such Connecticut patriots as Silas Deane, a future American diplomat, and Jeremiah Wadsworth, the future Commissary General for America’s French allies, Benjamin came to believe the British desired nothing less than to stamp out American liberty. In April 1775 word reached him of the bloodshed at Lexington and Concord, Massachusetts, and he journeyed north to British-occupied Boston where he took heart at the sight of thousands of militiamen besieging the town. Desiring to free his country from British oppression, Tallmadge quickly returned to Connecticut where he obtained a lieutenant’s commission in a local regiment, and within a year he faced the British in battle — almost literally in his back yard.

After the British evacuated Boston in March 1776, the Continental Army, now including young Benjamin Tallmadge, assumed defensive positions around New York City in anticipation of a British attack. Deployed to Long Island, Benjamin enjoyed a brief reunion with his family before taking up his assigned post at Bedford Pass, one of the critical passes leading directly to the American bastion at Brooklyn Heights. When the British attacked on August 27th, he fought off repeated enemy charges on his position, but despite his valiant efforts, he was forced to fall back with the rest of the army. Still, Lieutenant Tallmadge’s courage so impressed his superiors that he was chosen to hold the rear guard as the Continental Army escaped across the East River to Manhattan. In the weeks to come, he sporadically engaged the British as the Americans fell back across the island to White Plains, New York, just north of the city, where on October 28th he held Chatterton’s Hill, the key to the American right flank, against repeated Hessian attacks. As the Americans were forced back, Tallmadge was almost captured when a clergyman leapt on his horse, which threw both men into the swirling waters of the Bronx River. As British soldiers chased after him, the young lieutenant dashed up the opposite bank, leapt on his horse, and raced to alert General George Washington of the impending disaster. Following this defeat, Tallmadge remained in the Hudson Highlands as part of a force ordered to monitor the British forces in New York while Washington and the main Continental Army fell back into Pennsylvania, from where the Americans attacked enemy garrisons at Trenton and Princeton, New Jersey. Following these much-needed victories, Washington ordered the army’s reorganization as new recruits filled the ranks.

During this reorganization, Tallmadge’s Connecticut regiment disbanded, but he quickly signed on with the Second Continental Light Dragoons. Promoted to captain, he spent the winter outfitting the regiment with horses as well as carbines and pistols. He also instilled tight military discipline among the men and exhibited such a professional demeanor he was promoted to major in April 1777 at age twenty-three. That fall he led his men into action against the British in and around the nascent nation’s capital at Philadelphia. At the Battle of Germantown on October 4th, Tallmadge and his troops struck the British left flank and drove the enemy back. Soon, however, the assault broke down, and the British launched a counterattack, which routed the Americans. As soldiers fell back around him, Tallmadge desperately fought to stem the flood. Try as he might, however, the task proved impossible. Still, he refused to join those fleeing for their lives and led his men forward to hold the enemy back, just as he had at Brooklyn Heights. His defense helped slow the British long enough for the army to reach safety, though it could not save Philadelphia. With the defeat, the British spent the winter of 1777-78 enjoying the city’s comforts, but they were not left in peace. Tallmadge camped within a short distance of the city so as to monitor British activity, occasionally clashing with British cavalry patrols. As winter came to an end in early 1778, the British returned to their base at New York, and Washington and Tallmadge once again shifted their attention to that city and its environs.

With the British back in New York, Washington realized he needed reliable and accurate information regarding British forces; consequently, he appointed Major Benjamin Tallmadge as his chief spymaster. In this capacity, the major drafted his childhood friends Abraham Woodhull and Caleb Brewster, who lived on Long Island, as spies and received frequent reports from both men as well as from Robert Townsend, an operative who lived and worked in New York itself. As he read the reports, Tallmadge was incensed at the treatment of his fellow Long Islanders at the hands of British soldiers. Homes were occupied, and inhabitants were physically brutalized if they disagreed with their British masters. Rage soon blossomed into loathing, however, when he discovered that British soldiers had transformed his father’s church in Setauket into a barracks and destroyed the graveyard to construct fortifications. He immediately resolved to strike at the British and set his sights on the newly constructed Fort Franklin, named for Benjamin Franklin’s Loyalist son William, near Oyster Bay. On the night of September 5, 1779, Tallmadge and 130 dragoons, Continental troops and Long Islanders crossed Long Island Sound from Connecticut and marched on the fort. Approaching their objective, they came upon a contingent of Loyalist whaleboat men, and Tallmadge immediately ordered his men to charge. The Loyalists opened fire on the advancing Americans, but in moments, resistance crumbled as the Americans swept into camp. Most of the Loyalists were captured, but enough escaped to harass Tallmadge as he pressed on towards the enemy garrison. Realizing surprise was lost and the Redcoats were now prepared for him, he called off the attack and led his men back to Connecticut, but he refused to abandon his oppressed countrymen.

Almost immediately, Tallmadge began planning a second expedition across Long Island Sound, but he was soon sidetracked by Benedict Arnold’s treasonous plot to turn over the fort at West Point to the British. Only after the conspiracy was foiled and Arnold had fled to New York did Tallmadge return his attention to the British occupiers. In late fall 1780 he received a report from Abraham Woodhull detailing the construction of a new British stronghold, named Fort St. George, on the island’s south shore. He persuaded General Washington to approve an audacious strategy whereby he would cross over Long Island Sound and destroy the fort as well as a large supply of hay and forage at Coram. Accompanied by 100 dragoons, Tallmadge left his base at Stamford, Connecticut on November 21st and sailed across twenty miles of open water to Mt. Sinai. After being delayed nearly twenty-four hours due to a heavy rainstorm, he led his men on a daring night march across Long Island and arrived opposite Fort St. George at 3:00 a.m. on the 23rd. As he prepared to attack, he ordered the dragoons to leave their muskets unloaded — the fort would be taken at bayonet point. At 4:00 a.m. he charged forward with his men right behind him shouting “Washington and Glory!” In a matter of minutes, they were inside the fort, and the British were so overwhelmed they struck their colors, though a brief and brutal fight occurred as several soldiers fired on the Americans in the aftermath of the surrender. As the fighting ended, Tallmadge ordered his men to destroy the fort and a nearby supply ship. When that was done, he directed all but twelve men back to the boats. He then led his twelve comrades to Coram where they torched between 100 and 300 tons of supplies. Satisfied by all he had accomplished, he led his troops back to Connecticut where word of the triumph swept through the countryside. The young officer received praise from both General Washington and the Continental Congress, but he still yearned to restore all of Long Island to American control.

His desire to drive the British from the island did not abate, even as Washington focused his sights on the British army encamped at Yorktown, Virginia. While Washington led the main army south to defeat British General Lord Charles Cornwallis, Tallmadge and his men remained outside New York to convince the British commander-in-chief, General Sir Henry Clinton, that the true attack was poised against him. As part of that diversion effort, the daring major devised an attack on the British garrison at Fort Slongo, near the village of Huntington. On October 2nd his men embarked from Norwalk, Connecticut and crossed over to Long Island. They positioned themselves in front of the fort, and with a shout, they surged forward with such ferocity that only a solitary British soldier had time to fire his musket before fleeing for his life, not even bothering to shut the fort’s gate. Once inside the fort, Tallmadge’s soldiers engaged in heavy fighting with the defenders. In moments, all but a handful were prisoners. Knowing they could not stay long, the troops destroyed the bastion and the supplies they could not take with them and returned to the mainland where their comrades once again celebrated their exploits. On the other side of the line, Fort Slongo’s fall further demoralized those British officers and men already reeling from the disastrous defeat at Yorktown, and Tallmadge sought to further capitalize on their weariness. In November he led his raiders across Long Island Sound to gather intelligence, though he also seized the opportunity to engage in sabotage. During the expedition, he recognized that the war was winding down, but he wanted one more chance to strike at the hated enemy. In December 1782 he determined to strike a Loyalist force at Huntington, but weather and Loyalist whaleboats in Long Island Sound thwarted his designs, though he did capture two boats and their crews. He also captured two British privateers operating in Long Island Sound in February 1783. Shortly thereafter, he learned American and British diplomats had signed the Treaty of Paris ending the war, and in December he returned to his beloved Long Island, at last free of British oppression, thanks in no small part to his incessant forays against the British occupiers.

With the war over, Benjamin Tallmadge turned to more peaceful pursuits, though he did maintain an interest in national affairs. He settled in Litchfield, Connecticut and engaged in such business ventures as operating a merchant firm and selling real estate. Through these enterprises, he remained in close contact with George Washington, particularly during the general’s tenure as the country’s first president. Like his commander-in-chief, he ardently supported the strong, new government taking shape under the U.S. Constitution, and he became a staunch Federalist. After serving as Litchfield’s postmaster, Tallmadge was elected to the U.S. House of Representatives in 1800 where he joined in debating such critical issues as the War of 1812. He served a total of eight terms before leaving Congress in 1817. Interestingly, just before retiring, he voted against increasing pensions for the three Americans responsible for capturing British Major John Andre, who had turned the pliable Benedict Arnold into a traitor. Despite exiting politics, however, the aging warrior continued to correspond with his friends in Congress regarding matters of national importance, including vocally denouncing President Andrew Jackson’s decision to relocate the Cherokee Indians from Georgia to Oklahoma. He spent his last years at home in Litchfield writing his memoirs of the American Revolution. Benjamin Tallmadge died in early March 1835, and every newspaper to record his death began by honoring his gallant service along the shores of Long Island Sound.

Although espionage was the primary focus for many of his military exploits, Benjamin Tallmadge was so much more than just George Washington’s spymaster. He was a daring and energetic officer immune to danger and eager to risk all to secure victory for himself and for his cause. Like his commander-in-chief, he refused to abandon his post, and he relentlessly battled the British across the fields of Long Island until they were worn down and had no choice but to leave the U.S. for good. To his great credit as well, he continued to faithfully serve his beloved country long after the war ended. In evaluating Tallmadge’s military career, some believe his tenacity parallels that of another famous Continental officer, known to history as the “Swamp Fox.” For one so devoted to America, there could be no more fitting tribute than to label Major Benjamin Tallmadge as the “Francis Marion of the North.”

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