Sag Harbor Raid, Special Ops of the American Revolution

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In April, 1777, former British Royal Governor William Tryon, newly commissioned major general, led a strong detachment in a raid against an American military depot at Danbury, Connecticut. The Americans were caught off guard and could not bring enough troops to counter the destruction of much needed ammunition and provisions. Within three weeks of the British raid, the Americans would have their revenge. It was a bold and decisive attack that not only gave the British a black eye, but raised the moral of a nation desperate for good news… of any kind. It took a Connecticut colonel, newly exchanged from the disastrous wilderness trek and attack on Quebec, to exact revenge for the citizens of Connecticut. Colonel Return Jonathan Meigs would hand pick an elite force from among the American army’s best. He would cross twenty miles of open seas in whale boats, attack a British garrison with only the bayonet, burn and destroy tons of British storage and forage, and attack a twelve gun man-of-war, ultimately torching the war ship and nearly a dozen other British vessels. Not only that, the raid would cover over ninety miles in twenty five hours, most in the dead of night, capture over ninety loyalist soldiers, kill six of the enemy, and all without a single loss of life; not even wounded. In the annals of the war, or any war, the planning, execution, and results of this raid was anything but miraculous.

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Map of British General Tyron’s route to Danbury Connecticut and back

British Danbury Raid

In the spring of 1777, the British must have been aware of General Samuel Holden Parson’s orders to reorganize the New England regiments at Peekskill, NY. While the Continental regiments were either in Peekskill or scattered throughout the area, many unarmed, the former royal governor of New York, now Major General William Tryon, struck Connecticut. From April 25 – 28, he commanded an expedition of 1,850 regulars and loyalists against Danbury, an important military depot some 25 miles inland from the Long Island Sound. General Gold Silliman and 120 militiamen were posted at Danbury to guard the depot. Faced with such a superior enemy, he quickly retreated as the British force approached. Tryon made Danbury within 24 hours of landing at Compo Beach, present day Westport. His men immediately set to work destroying much needed military supplies and food including torching twenty one storehouses and several homes, sparing known Tory residences. Word traveled and rebel commanders desperately tried to organize enough men to offer a resistance to the marauding British.

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Battle of Ridgefield. Gen. David Wooster attacks British Gen. Tyron’s troops. Wooster is mortally wounded.

By the time Tryon began his retreat back to his ships, Major General David Wooster, along with Generals Gold Silliman and Benedict Arnold had assembled only 500 men. It was decided that Wooster would pursue the British, striking when he could. Meanwhile Arnold and Silliman, still gathering arriving militiamen, rushed forward to cut off the British. Wooster attacked at Ridgefield and was mortally wounded, dying a week later, however he was able to avert the British onto the Ridgefield Road where Arnold and Silliman had set up a strong defense of 400 men. The Americans held their ground temporarily and inflicted casualties, but had to fall back under superior numbers. The next day the British were able to advert Arnold’s defensive position and successfully arrived at their ships. The damage done to a critical storage of provisions and the new nation’s moral was huge.

American Response

Map of Meigs Raid
Map of Meig’s Raid

General Samuel Holden Parsons was fuming after Tryon’s raid and sought a proper response. He had information that the British were foraging along the east coast of Long Island to supply their army in New York City. He devised a bold plan to attack the foraging party while also destroying British supplies and shipping. He sought the proper troops to see it through and chose Colonel Meigs. Newly commissioned commander of the 6th Connecticut, Meigs was careful in his selection of men comprising the raid: fourteen officers (including Major Humphrey) and 220 enlisted regulars. Mostly light infantrymen, he picked those he believed were of strong stamina and courage. That and sound planning plus accurate intelligence would prove to contribute to the operation’s incredible success.

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Colonel Return Jonathan Meigs. Later image after the war when he was an Indian agent in Ohio.

Colonel Return Jonathan Meigs (1754-1823)was a hatter by trade as had been his father. When war erupted, he soon showed his natural qualities as a military leader, chosen as a captain of minutemen. Soon after Lexington and Concord, he was commissioned a major in the 2nd Connecticut Continental Regiment. Within in two months, he would command a division in Colonel Benedict Arnold’s horrendous trek through the Maine wilderness and subsequent failed attack on Quebec on December 31, 1775. His division would fight the longest and was the last to surrender after surrounded with no hope of escape. British General Guy Carleton treated Meigs with great respect and paroled the American major to return home. As soon as word reached Meigs that he was exchanged, freeing him to re-enlist, he did so and was commissioned a Lt. Colonel. When American General Samuel Holden Parsons needed a hard fighting, stubborn fighter, and experienced leader to head the bold raid, he had his man in Meigs.

General Samuel Holden Parsons
General Samuel Holden Parsons

The plan was threefold: attack British outposts in the vicinity of Sag Harbor, Long Island, destroy the forage that had been collected, and finally capture or destroy any shipping in the harbor. They arranged for the whale boats to meet his troops at Guilford, Connecticut, crewed by among the most experienced seamen living on the Connecticut coast – fishermen and those who traded along the Long Island Sound prior to the war. They would row the approximately 20 miles across the sound, enter Gardiners Bay, which sections and cuts into the tip of Long Island, and while still under the cover of darkness, row to Southhold and Peconic Bays where they would disembark. The crossing, in the dead of night, would be hazardous; fog, squalls, tidal currents, high winds, rough seas, were a possibility alng with British men-of-war which prowled the sound daily.

For intelligence, Meigs turned to a sergeant from the 1st Connecticut who had escaped across the sound with other patriots on Long Island after the British captured New York City, Sergeant Elnathan Jennings. Jennings (1754-1840) was 23 years old and up until the previous year, had spent his entire life in the Sag Harbor region. He gave details of what they should expect upon landing, the best place to put in, paths to take, and the village in general. He informed Meigs of an unguarded back way into the village across the fields and ponds where he had played as a boy. Jennings seemed to take credit for the venture, later writing, “I volunteered myself to Colonel Meigs, stating the situation of Sag Harbor and the strength of the British guard and how easy they might be taken, and that I would pilot him and a detachment of troops across the sound to Long Island… The colonel was highly pleased with my plan…”

The raiding party departed New Haven Connecticut on the 21st, arriving Guilford where they waited two days for better weather. At 1 PM on the 23rd, they departed for Long Island in the company of three sloops of war, one unarmed. They rowed across the sound and arrived on the North Fork on the western side of the Island where eleven boats were carried over the slip of land, put into the Peconic River, and crossed to Long Island (Present day Foster Town Beach), quietly hauling up at 2 AM on the 24th. Guards were set and Meigs took off for the town and garrisons. About sixty British loyalists, both posted and part of the foraging party, were in the town. During the four mile march south then east around the bay, so to come upon the town from behind, they silenced British sentry posts, taking prisoners.

The next is related by Sag Harbor village historian, William Mulvihill; “they captured the British guardhouse, which was the schoolhouse where Jennings learned his alphabet… They marched silently to the British barracks and took more than 30 prisoners without firing a shot. Then they went on to Main Street, where the American Hotel is now, and captured the British commander and his staff. Next they marched up the hill to the Old Burying Ground and attacked the fort there, killing five or six redcoats and taking 56 more prisoners.” The Old Burying Ground was one of the first grave sites in Sag Harbor. The British had cleared trees and, according to horrified residents, desecrated the graves as they set up a fortification to defend the port, it being the highest available ground. Light infantryman Christopher Vail wrote, “We proceed down to their quarters where we completely succeeded in capturing the whole force except one man. We burnt all the coasting vessels, which were all loaded and laid alongside the wharf, and a store that was sixty feet long that stood on the wharf…”

As Meigs approached the water front, a 12 gun schooner spotted the raiders. The alarm was given and the British ship opened fire with grape and round shot. The schooner was anchored within range of Meigs’ muskets who returned fire for the next forty five minutes. While the musket fire kept the crew pinned down, the rest of the raiding party set fire to the ships and stores along the wharf. Tory prisoners were rounded up – a member of the raiding party wrote, “…When we arrived we took 99 Tories. Some had nothing but his shirt on, some a pair of trousers, others perhaps one stocking and one shoe and in fact they were carried off in their situation to New Haven…” General Parsons wrote a detailed letter to General Washington the very next day after Meigs’ party returned to Connecticut. It explains the actions at Sag Harbor succinctly and is worth presenting here in its entirety with slight edits.

Tip of Long Island showing Gardiners Bay Sag Harbor and Peconic
Tip of Long Island illustrating Gardiner’s Bay, Sag Harbor, Peconic River, and Long Island – strip of land to the left and east of Sag Harbor.

New Haven, May 25, 1777. Having received information that the enemy were collecting forage… on the east end of Long Island, I ordered a detachment from the several regiments then at this place, consisting of one major, four captains, viz: Troop, Pond, Mansfield, and Savage, and nine subalterns, and two hundred and twenty men, non-commissioned officers and privates, under the command of Colonel Meigs, to attack their different posts on that part of the Island, and destroy forage, &c, which they had collected. Col. Meigs embarked his men here, in thirteen whale boats, the 21st, and proceeded to Guilford, but the wind proving high and the sea rough, could not pass the sound until Friday, the 23rd. He left Guilford at 1:00 on the afternoon of the 23rd, with one hundred and seventy of his detachment, and under convoy of two armed sloops, and in company with another unarmed, (to bring off prisoners), crossed the sound to the north branch of the island near Southold, where he arrived about 6 o’clock in the evening; the enemy’s troops on this branch of the island had marched for New York two days before; but about sixty of the enemy remaining at a place called Sag Harbor, about fifteen miles distant on the south branch of the island.

Meigs hauled whale boats across the island
Whale boats carted over land to cross Peconic Bay in route to Long Beach near Sag Harbor.

He ordered eleven whale boats, with as many men as could be safely transported across the bay, over the land to the bay, where they re-embarked to the number of one hundred and thirty, and at about 12:00 o’clock arrived safe across the bay, within four miles of the harbor, where having secured the boats in the woods under care of a guard, Colonel Meigs formed his little remaining detachment in proper order for attacking the different posts and quarters of the enemy, and securing the vessels and forage at the same time. They marched in the greatest order and silence, and at 2:0 o’clock arrived at the harbor.

The several divisions, with fixed bayonets, attacked the guards and posts assigned them, whilst Captain Troop, with the detachment under his command, secured the vessels and forage lying at the wharf. The alarm soon became general, when an armed schooner of 12 guns and 70 men, within one hundred and fifty yards of the wharf, began a fire upon our troops, which continued without cessation for three-quarters of an hour, with grape and round shot, but the troops with the greatest intrepidity returned the fire upon the schooner and set fire to the vessels and forage and killed and captured all the soldiers and sailors, except about six, who made their escape under cover of the night. Twelve brigs and sloops, one an armed vessel with 12 guns, about 120 tons of pressed hay, oats, corn and other forage, ten hogsheads of rum and a large quantity of other merchandise, were entirely consumed. It gives me the greatest satisfaction to hear the officers and soldiers without exception, behaved with the greatest bravery, order and intrepidity.

Colonel Meigs having finished the business on which he was sent, returned safe with all his men to Guilford by 2 o’clock PM yesterday, with ninety prisoners, having in 24 hours, by land and water, transported his men full 90 miles, and succeeded in his attempts beyond my most sanguine expectations, without losing a single man, either killed or wounded. It gives me singular pleasure to hear no disposition appeared in any one soldier to plunder the inhabitants or violate private property in the smallest degree,.. Major Humphreys, who waits on your Excellency with the account, was in the action with Colonel Meigs, and will be able to give any further necessary information. I am &c, To General Washington. Saml. H. Parsons.

Major Humphreys delivered the letter to Washington at army headquarters at Middlebrook, New York. Washington immediately wrote back on May 29th, “I am now favored with your letter of the 25th, by Major Humphrey. The intelligence communicated by it is truly interesting and agreeable. And now I shall take occasion not only to give you my hearty approbation on your conduct in planning the expedition to Long Island, but to return my sincere thanks to Lieut. Col Meigs and all the officers and men engaged in it. [By the time Washington had penned this letter, Meigs had been commissioned a full colonel nearly two weeks previously – his predecessor, Colonel William Douglass, having died on the 28th]. The enterprise, so fortunate in the execution will greatly distress the enemy in the important and essential article of forage, and reflects much honor upon those who performed it. I shall ever be happy to reward merit when in my power, and therefore wish for you to enquirer for a vacant ensigncy for Sergeant Jennings, to which you will promote him, advising me of the same and the time. I am Sir, &c., G. Washington.”

Old Burial Ground. Site of British garrison.
Old Burial Ground, Sag Harbor, Long Island. Site of British garrison.

Colonel Meigs would receive a commemorative sword from Congress, recognized for “prudence, activity, enterprise and valor.” For whatever reason, Sergeant Jennings would never receive his commission as an officer. A search of published rosters of Continental and militia soldiers of the Revolution list Jennings as a sergeant right up until he was released from the army in June of 1779. Colonel Meigs would return to his newly assigned regiment awaiting his next posting. Several Connecticut regiments would march with Washington’s army to Philadelphia and fight at Brandywine and German Town. Some would head north to General Gates to help counter British General Burgoyne’s invasion from Canada. Meigs would remain with the army around the Hudson Valley, assigned to build the fortifications at West Point.

More Reading about Raids during the American Revolution, Special Ops, and the Sag Harbor Raid. Preview these books on Amazon.

Also on Revolutionary War Journal

SOURCES

Meigs, Return Jonathan. Journal of the Expedition Against Quebec, Under the Command of Col. Benedict Arnold, in the Year 1775. 1864: Privately Printed, New York, NY.

Hall, Charles. Life and Letters of Samuel Holden Parsons; Major General in the Continental Army… 1905: Otseningo Publishing Co., Binghamton, New York.

The Hartford Courant. “Colonel Return Jonathan Miegs, From Local hatter to War Hero, Pioneer and Diplomat. (April 22, 1998).

Heitman, Francis B. Historical Register of Officers of the Continental Army During the War of the Revolution. 1914: The Rare Book Shop Publishing Company, Inc., Washington D. C.

Smith, Stephen & Camp Frederick & Barbour Lucius & White George – Attorney Generals. Record of Service of Connecticut Men I. War of the Revolution…” 1889: Hartford, Connecticut.

Tonsetic, Robert L. Special Operations in the American Revolution. 2013: Casemate Publ., Haverstown, PA.