Forgotten Warriors of the American Revolution: For Liberty, Colonel William Douglas Sacrificed His Money, Health & Life

Colonel William Douglas (January 27, 1742- May 28, 1777) from North Branford, Connecticut was a successful merchant mariner and later farmer – honest, fair, hardworking, and successful in business. He was also a tragic figure, having invested and lost everything he had for the cause of liberty – his fortune, his family’s future, his health, and ultimately his life. A passionate patriot from the opening shots of the American Revolution, after a year and a half of hard campaigning, pouring all his time and money into his regiment, and having faced incredible hardships and setbacks in battle while fighting a deteriorating body, he died young and penniless while still in command of his men. Perhaps, because his time in history was short lived, or his efforts were consumed by defeat and the early pangs of citizen soldiers learning how to fight, his commitment and contributions to America’s founding have been brushed aside and overlooked. Our textbooks can only contain so many names of those who fought for their beliefs in establishing a new nation founded on a government ruled by the people. As such, those who poured all their efforts into the cause from early on, men like Dr. Warren and William Douglas, who faded from the fields of battle soon after hostilities erupted, so too faded from the minds of a grateful people.

At first, I was preparing to write a brief article on Colonel Douglas, similar to others presently on the internet. But once reading through the thirty-six letters that have survived, those he penned to his wife while campaigning, I knew he deserved far more attention than a mere seven hundred words. Those letters spoke of a deeply religious man who expressed tender love for his wife and family. It was a love he also shared for his “little country”, time and again expressing his willingness to sacrifice everything, for the cause of liberty. We owe our deepest gratitude and eternal thanks to those Forefathers who unselfishly, without self-motives of greed or prestige, gave their all so others and future generations could live in a free and prosperous society.

Early History

William Douglas was born in Plainfield, Connecticut on January 27, 1742.  He was the third child of parents Lt. Colonel John Douglas (Jul. 28, 1703- April 20, 1766) and Olive Spaulding Douglas (Feb. 21, 1709- Jan. 17, 1753). Little is known of his childhood, except that he and his siblings received an excellent education, his brother Benjamin having studied law at Yale. His family was well established in the Plainfield area of Connecticut and little doubt that they were comfortable financially. His father John was an officer in the local militia, however, most likely because of his advanced age at the time, there are no records of his participation in the French & Indian War. When war between England and France broke out, there were several early setbacks for the British and English settlements. By 1758, the British government, under William Pitt, ordered that 20,000 provincial troops were to be raised in which Connecticut was to provide 5,000 soldiers. At the age of 16, Douglas was part of Connecticut’s levee and enlisted in the state militia, later serving with Israel Putnam (later Major General in the American Revolution). William Douglas of Plainfield is listed in the 1759 roster as clerk (perhaps for his keen intellect) in the 10^th company, Captain George Crary commanding, of the 4^th regiment under Colonel Eleazer Fitch. Lt. Colonel Israel Putnam is second in command of the 4^th and captain of the 2^nd Company. After participating with Fitch’s regiment in British General Wolfe’s successful capture of the city and fortress of Quebec in 1759, William returned home to Plainfield.

William had three siblings, as noted, all well-educated and prominent members of the community. The oldest was John Douglas (April 12, 1734 – Sept. 22, 1809). He, like William, served in the American Revolution from the opening of hostilities – first as a minuteman in Capt. Holmes company, a Lt. Colonel in the 8^th Connecticut Militia under Colonel Jedediah Huntington, early 1776 he declined to serve as Colonel of Colonel Mott’s regiment and accepted the command of the 21^st Militia Regiment and was posted under Gen. Spencer in Rhode Island until 1777 when he was commissioned Brigadier General of Connecticut’s 5^th Brigade of Militia until the end of the war. It was stated that by war’s end “John Douglas was a man of no little importance in the town.” Williams’ other brother, Benjamin (Aug. 1739 – Dec. 3, 1775), had gone on to Yale to study Law and was a successful banister and Kings Attorney and was on course to become a prominent legislature for the patriot cause until illness struck him down early in life. The youngest, his sister Sarah Douglas Perkins, remained in the Plainfield area (April 18, 1744 – Aug. 10, 1795).

After the French & Indian War, William used his talents to become a successful merchant and shipmaster, trading with partners in the West Indies. He made a considerable fortune during these ventures and on July 5, 1767, he married Hanna Mansfield of New Haven, Connecticut (Nov. 17, 1747 – May 22, 1825). He soon purchased 150 acres of land in Northford, about 10 miles from New Haven and present day North Branford in the Long Island Sound region, and in 1772, settled his family there. He continued his business ventures and invested in property in the Northfield and Hartford Connecticut area.

He was considered very successful and a prominent member of the community. Hannah and he would have four children: Olive Douglas Fowler (March 25, 1768 – July 24, 1828), William Douglas (Feb. 23 – Sept. 14, 1823), Hannah Douglas Dutton (April 12, 1772 – July 12, 1853), John Douglas (March 24, 1775 – Feb. 20, 1784). Life in general was very bright for Douglas. He had made his mark as a seaman trading in the West Indies, a man of means in land with a substantial fortune, a secure and healthy family, and he was basically able to retire to the countryside, a respected and sought-after member of his region. The war and his firm commitment to its cause tragically changed all that.

Start of the American Revolution – Campaign with the Northern Army and Invasion of Canada

On May 10^th, 1775, Ethan Allen, leading a rowdy bunch of backwoodsmen who titled themselves Green Mountain Boys, along with around fifty Connecticut volunteers and a self-assured officer with a commission from Massachusetts, Benedict Arnold, captured the British garrison at Fort Ticonderoga, New York, located on the narrows of Lake Champlain. It was a key fort commanding the approach to the colonies from the north and west. But more so of interest to the Americans, it had over a hundred cannon along with power, shot, and a large stand of small arms. All waiting to be snatched up and put to good use against their owners, the British army. According to some internet sites, without citations, William Douglas was a member of the Connecticut volunteers who accompanied Ethan Allen’s men during the capture of the fort. Having checked Connecticut state rosters of the Connecticut men who led and organized the volunteer group, Douglas’ name does not appear. Therefore, without proof, one can only speculate if Douglas, who was by then a keen patriot, had joined the volunteer group to place the fort and all its provisions in the hands of patriots.

As mentioned, all three brothers, and possibly William’s sister, were avid patriots. The oldest John, having joined the minutemen, Benjamin, who was active in legislative pursuits, and William, whose previous war time experience as a teenager during the French and Indian War made him a prime candidate for a leadership role in Connecticut’s drive to raise new levees to battle the British. By April, 1775, with the outbreak of hostilities at Lexington and Concord, the Connecticut Provincial Government raised eight full regiments. Five were sent to Boston to lay siege to the British who were confined to the city, and three were sent north to Commanding General Philip Schuyler and General Richard Montgomery (former British officer of New York) in their planned invasion of Canada. Of the three sent north, one, the 4^th Conn., was under Colonel Benjamin Hinman, another, the 5^th Conn., led by Colonel Samuel Holden Parsons, and the third, the 1^st Connecticut Regiment, Douglas’ unit, was commanded by General David Wooster. Aged 64 and Yale graduate, Wooster commanded troops for the whole of the French & Indian War and would later die of wounds received during the Battle of Ridgefield, April 27, 1777. Wooster’s regiment was raised on the first call by the Connecticut Assembly from the Hartford region and was organized on May 1, 1775.

Records list Captain William Douglas of Northford commanding the 6^th company of ten companies in the 1^st Connecticut Regiment under General Wooster. On June 13, 1775, Douglas was appointed aide-de-camp to Wooster, while still obtaining command of his company. So too was Captain Benedict Arnold originally assigned a company in Wooster’s regiment, the 5^th, however he would later accept a commission in May, 1775, as colonel from the Massachusetts Assembly and by September, 1775, lead a force up through the Maine Wilderness to launch an attack against Quebec. Captain Douglas would assume duel rolls as company commander and aide-de-camp throughout his time with the 1^st Connecticut. On June 19^th, the 1^st Conn., along with the 5^th Conn., marched south to Harlem, New York, just north of the city, by request of the New York Provincial authorities and the Continental Congress and encamped on June 28^th. During the next two months, much of General Wooster’s men guarded stock on Long Island.

By mid-summer, plans were in place to affect an invasion of Canada under Generals Phillip Schuyler and Richard Montgomery, advancing up the Hudson Valley and down Lake Champlain to attack the forts on the Richelieu River before capturing Montreal and Quebec. Colonel Benedict Arnold would command another force who would traverse through the wilderness of Maine to attack Quebec directly. In early July, Wooster’s men, along with the 5^th Conn., marched to the Northern Army stationed at Albany and Fort Ticonderoga, NY.  Letters from Douglas to his wife indicate their progress: July 19^th he was in Albany, August 28th in Ticonderoga, Crown Point on the 29^th, and Isle aux Noix on the Richelieu River on September 16^th. Wooster’s force, along with the 5^th Conn., continued down Lake Champlain to the Richelieu River where Generals Schuyler and Montgomery, along with the 4^th Conn., had laid siege to Fort John (Fort Jean) on September 17, 1775.

The British had constructed a fort at St. John’s, situated on the Richelieu River, to guard against any advance towards Montreal. It had been lightly garrisoned when Ethan Allen and his Green Mountain Boys raided the fort on May 18, 1775, sinking the HMS Savage, a six-gun sloop, fifty-footer with a crew of approximately fifty. This action prompted British General Guy Carleton to send a large contingency of regular infantry to occupy the fort. By the time the American Army approached the garrison in early September, there were 750 men posted under the command of British Major Charles Preston. Most were regulars from the 7^th & 26^th Regiments of Foot and the Royal Artillery. Ninety locally raised militia and twenty loyalists from Colonel Maclean’s Royal Highland Emigrants joined them. So too, the HMS Savage was raised and repaired.

Because of Douglas’ experience as a seaman, soon after his regiment arrived on Lake Champlain, he was given command of the two row galley gun boats that were well maned and carried twelve-pound cannon. Eventually he would command the flotilla of the American’s armed vessels. In a letter from General Schuyler to Washington, dated Sept. 20, 1775, he describes an action involving Douglas’ gunship that occurred in mid-September. Schuyler wrote, “You will perceive… that some of the Enemy’s Boats fired on our People, Capt. Douglas who commands one of our armed Boats pointed and fired a twelve Pounder loaded with Ball and Grape Shot at them and We have Accounts that about thirty of the Unfriendly Canadians were killed or drowned.” So too Douglas wrote to his wife of the action on Sept, 16, “As I had the Command of our water Craft, I Lay in the front of the whole, where I Plainly Discovered the first fire of the enemy, on the 500 men we had landed from boats and an ambuscade Laid on Shore for us. I Soon Made toward them, gave their bots a few Shot, with a twelve Pound Canon which made their fire Soon to Seise. Our men on Shore Kiled three on the Spot & by the Intelligence of twenty Canadiens, the Shots I gave them Sunk a boat with thirty-eight men on board and wounded Several in other boats.” (From Douglas Letters).

The siege, initiated on September 17^th lasted nearly two months. Early on, Gen. Schuyler took ill and turned command of the operation over to General Montgomery. British Major Preston’s hopes of reinforcements were dashed when a relief column sent by General Carleton, now in Montreal, was turned back. He surrendered on November 3^rd and ten days later, the American army under General Montgomery, marched unopposed into Montreal, Carleton having barely escaped the day before on the 11^th. Douglas and the 1^st Conn. was stationed in and around Montreal during the rest of their brief stay in the region. Casualties on both sides during the siege was light, but the Americans suffered most severely from a reduction in men due to extensive sickness (a massive outbreak of small pox that killed hundreds) and multiple furloughs. On October 23^rd, Douglas informed his wife Hannah that he had taken on a cold while walking the swamps to make discoveries around the fort at St. Johns. This was the first indication of illness that would dog him throughout the remainder of his military career and ultimately take his life.

Both the 1^st and 5^th Connecticut Regiments were shattered and ceased to be an effective fighting force.  Between October and November 28^th, both regiments were broken up and the units disbanded, the survivors, individually and in groups, returned home. Colonel William Douglas, so too physically broken and worn out, returned home to Northford, Connecticut. General Wooster would remain in Montreal with only 150 men from the combined forces to garrison Montreal. General Montgomery, with a small force, would march to Quebec to join Arnold in their attempt to take Quebec on December 31, 1775. Montgomery would be killed and Arnold would be wounded in what became a slow and general retreat from Canada until the summer of 1776.

Major in Colonel Andrew Ward’s Regiment – Late February through April, 1776 – Building Fortifications Around New York City

By the end of November, 1775, after the regiment dissolved, Douglas had returned home in ill health. He had a severe cough and had nearly lost his voice. He remained at home, intending to recuperate, however when the Connecticut Assembly called for a body of men to help build the defenses in New York City, he once more answered the call. General Charles Lee was determined to rid New York City of its large population of Tory leaders. He convinced Washington to allow him to raise a regiment from Connecticut to construct city defenses, while accomplishing his main goal of imprisoning Loyalists. With the help of Colonel David Waterbury, who shared Lee’s vehement dislike of Tories, he marched a regiment toward New York on Jan. 8^th. As recorded, the wisdom of the movement was questioned and Congress called off the operation. Lee would not be put off. He convinced the governor and Council of Safety for Connecticut to reassemble Waterbury’s regiment. A call went out on January 26^th that included raising another regiment to join Waterbury’s unit. Seven hundred and fifty men to comprise each regiment “to join and assist Major General Lee… that they should be entitled to the same pay as allowed the troops before Boston and dismissed soon, when the service would admit.” Men responded, twelve hundred in all, including William Douglas. Colonel Andrew Ward was named commander with now Major William Douglas accompanying the regiment to New York City. They were kept busy erecting forts for two months, when they were verbally discharged by General John Sullivan who took over from Gen. Lee who had been sent south to Charlestown, South Carolina to help thwart an invasion by British General Henry Clinton. (pg. 489 Andrew Ward and His Decedents)

Ward’s regiment was put to work on Long Island constructing what would become Fort Stirling on Brooklyn Heights. Douglas writes to his wife, dated Feb. 26^th: “Our Regiment is now stationed on Long Island at and about the ferry. We shall soon begin a fortification on this side that will command the East River and the town. [Fort Stirling – Named for Gen. William Alexander (Lord Stirling)]  (pg. ii67 Johnston Battles Around NY)]. The troops in the City are fortifying in one of the Streets that will command the old fort, if the Enemy should get possession of it, (and are putting down the rear of the fort.) [This is Fort George – Lee ordered the walls facing the city be torn down – if the British scaled the fort, then American batteries positioned up Broadway could fire upon them.] We have begun another Fort near “Hell Gate.” The men of war have dropped down below the town and are very quiet, but supplied from the City by orders of this Congress. Our troops are very hearty and fare well…” Later in the same year, after the Battle of Long Island (also known as the Battle of Brooklyn), and with the Americans withdrawing to the city, Douglas writes again to his wife on Aug. 31^st, commenting on his previous time in New York constructing Fort Stirling: “The shipping lay now close by the city, and can in half an hour be abreast of it with the tide. I expect we [shall] soon have a cannonade from our own battery on Long Island, (Fort Sterling) which I have the mortification to think I helped build myself, in cold tedious weather!”

Commissioned Colonel of the Connecticut 5th State Militia under General James Wadsworth – Begins to use personal funds to supply his troops.

By mid-April, 1776, General Sullivan dismissed Ward’s Regiment and the regiment returned to Connecticut. Douglas went home and was about to begin a political career (having been elected to the Connecticut General Assembly, however it was not to be. In proportion to its population, no state contributed more men to the Continental Army than Connecticut. During the crisis that led to the battles fought in New York City from the summer of 1776 to Washington’s hasty retreat across New Jersey, Connecticut sent to New York, six continental battalions, seven “new state levies” of militiamen, and twelve additional regiments of militia. Douglas’ was to command one of the state levies who had enlisted for six months only – their enlistment ending officially on December 20, 1776. In June, 1776, Brigadier General James Wadsworth was given command of the seven state regiments. The commanders of Wadsworth’s Brigade are as follows: 1^st – Silliman, 2^nd – Gay, 3^rd – Sage, 4^th – Selden, 5^th – Douglas, 6^th – Chester, and the seventh was not numbered known as Colonel Bradley’s Regiment.

On June 20^th, Douglas received his commission as colonel of the 5^th battalion in Wadsworth’s brigade. Money to provide for equipment, supplies, and uniforms was scarce to non-existent. Each commander of individual units did what they could to prepare their men to fight in the coming battles. Douglas, a passionate and able soldier, had the financial means and spent freely, digging into his own pockets and advancing the funds to equip his men for the hardships he knew lay ahead. What quickly became known as the Douglas State Militia, raised from the New Haven Connecticut region, numbered 506 men by the time they arrived in New York City to reinforce Washington’s army busy preparing for an expected British invasion of the city and Long Island.

Wadsworth’s brigade boarded transports and sailed along the sound through Hell’s Gate and docked in the city where Douglas’ regiment encamped near Stone Street on the southwest angle of the city. We know that the last of Douglas’ regiment had arrived in New York City around the first week of August. Joseph Plumb Martin, a private in the regiment wrote in his memoir, “…Soon after my arrival in New York, a  forty-four gun ship (the Phoenix) and a small frigate (the Rose, I think) came down the North & Hudson River (they had been some time in the river) and passed the city in fine style, midst a cannonade from all our fortification…”  The HMS Phoenix & Rose had first run the Hudson River blockades on July 12^th to the Tappan Sea, up river where the Hudson widens. The action Martin referred to occurred on August 16^th. American fire ships drove the two British war ships out of the Tappan Sea and they sailed back down the river through a gauntlet of shore batteries. Douglas wrote of this incident – 4 American artillerymen were killed by their own rashness in loading and firing the cannon – no damage was done the British. He wrote that his regiment marched along Broadway and encamped on Broad Street. At that time Wadsworth’s Brigade and the Douglass State Regiment was assigned to Major General Joseph Spencer’s Division. Douglas wrote to his wife on July 27^th that he dined with Washington: “I had the Honor to dine with his Excellency Genl. Washington day before yesterday at which time he had nothing new from any quarter…”

During this time, Washington’s army swelled and shrank by a continuous flow of short-term enlistments representing all the colonies. Wadsworth’s Brigade, in which Douglas commanded a battalion, served for only six months. Twelve additional Connecticut militia regiments under General Oliver Wolcott showed up, but his men had served for only several weeks. Nine more militia regiments from the eastern counties of Connecticut under General Saltonstall also made a brief appearance before eventually going home before the year was out. So too a troop of horse appeared, but were sent home by Washington who did not at the time appreciate the importance of horse for intelligence and communication. It was recorded that all these ‘unmilitary-like’ troops failed to add much to the army’s efficiency – the men being generally poorly armed and undisciplined. Douglas complained of the quality of militiamen he was given to command, writing to his wife in letters in which he often griped that they were ill-equipped for battle and that they “give me much fatigue and trouble.” Also, throughout his letters home, he reiterated his firm commitment to the patriot cause. On July 20^th, 1776, he wrote that “little loss in finances is trifling in comparison to the loss in their country.” He continued that they “must freely suffer these inconveniences and stand forward…useful in the redemption of their country which will be a most noble reward for all that they suffer.” He spent freely from his own funds on his regiment and men, reassuring himself that any investment he personally made would pay dividends for a future that guaranteed liberty from the bonds of their mother country.

The British armada began to arrive at New York’s Harbor in early July, 1776. On July 3^rd, they began to land troops on Statin Island.  Because of Douglas’ sound experience as shipmaster, he was kept busy supervising defenses all along the water passages surrounding the city and Long Island including sounding the river and sinking hulks in the harbor. As British ships continued to arrive he wrote to his wife on Aug. 13^th, “There was 43 large ships came in yesterday – 31 Ships, 10 Brigs & one Scow. I am now going to sound the channel to see if it will not do to sink some vessels against the fort… [Hulks were ultimately sunk off Governor’s Island and the Battery in the East River Channel]. On August 23, a few days before the Battle of Long Island, Douglas wrote his wife about their position and the newly arrived Connecticut regiments, “… The Enemy landed yesterday on Long Island, at Gravesend, about nine miles from our lines; our flying parties are annoying them all the while. We have reinforced our side and I hope will be able to make a good stand… Our fire ships in the North River [Hudson River] have behaved manfully, have burnt one of their tenders… Our Connecticut Militia have come in bravely; twelve Regts were on the grand parade yesterday at one time! Almost one half of the grand army now consists of Connecticut Troops…”

Battle of Long Island, August 27, 1776

Douglas’ State Militia would ferry over to Long Island on Aug. 27, 1776. At the Battle of Long Island, they would serve on the extreme right line of the works, opposite the mouth of Gowanus Creek. There, with Captain Thomas’ Maryland Independent Company and two pieces of artillery, they stood ready to prevent pursuit of the retreating party by the enemy. Of the rest of Wadsworth’s command: Colonels Silliman, Sage, Chester and been sent to Long Island prior to the day of the battle, Douglas arriving that day. Bradley’s regiment was assigned to Fort Washington further north on Manhattan Island, and Gay’s regiment had remained in the city. Joseph Plumb Martin, a private in Douglas’ 3^rd company under Captain Peck, wrote of his regiment’s experience during that eventful day. He mentions that Douglas was not present, however it appears that he was not present during the ferrying of his men, but during and after the action, he was with his regiment on the ground.

Private Martin wrote: “…our sergeant major… soon arrived and informed us… that he had orders… to march us to our quarters as the regiment was ordered to Long Island, the British having landed in force there.” The regiment took the ferry to Brooklyn under the command of Lt. Col. James Arnold (Douglas was not present). They witnessed wounded being brought to the rear and marched to the sound of battle, “…pressed forward toward a creek, where a large party of Americans and British were engaged…” This was Gowanus Creek, where General Stirling & Major Gist, with a detachment of Col. Smallwood’s Marylanders, attacked and held off the British advance, allowing over 1,600 Americans to escape.  Martin continued, “By the time we arrived, the enemy had driven our men into the creek, or rather mill pond (the tide being up), where such as could swim got across… The British, having several field pieces stationed by a brick house [the Vechte-Cortelyou House], were pouring the canister and grape upon the Americans like a shower of hail… they came out of the water and mud to us looking like river rats, it was a truly pitiful sight…some of us went into the water after the fall of the tide, and took out a number of corpses.”

The pond Martin spoke of was the Brouwer’s Mill Pond. The remains of Stirling’s division had driven through the waters in a desperate bid to defy capture or death. Stirling’s detachment of between three and four hundred young men repeatedly attacked the British to assure their comrades’ escape, resulting in over 270 killed – only twelve made it back to the American lines. Stirling fought his way to the Hessians and offered his surrender. Douglas’ regiment “lay on the ground we then occupied the following night.” The next day they participated in a heated skirmish that involved the entire regiment and the following evening, were secretly whisked back across the East River to New York City with the rest of the American force stationed on Brooklyn Heights.

Douglas wrote of his experience to his wife on Aug. 31, 1776: “I take this as the first opportunity to acquaint you that on Tuesday last, we got a severe flogging on Long Island. We took twenty-one, which I am a witness to, as they came through my Reg^t as I was in the woods for a covering party, and to prevent the enemy from flanking our right wing. We were prevented from getting even one shot at them by a large creek [Gowanus Creek] which we could not cross. I remained at the most extreme part of the right wing of our Army in a thick wood to prevent their crossing a creek, where our sentry’s could hail and often fire at each other, until night before last when I received orders to call in my guard all, and march immediately with the utmost silence, which was soon done, and the whole army retreated into this city.” (Johnston Battles Around NY, pg. ii70). Douglas wrote that “of our army, took many, killed some and the rest got off…By the best account we killed more of them than they did of us. But they took the most prisoners…” (Battles of NY, Johnston pg. 221).

Eroding Health and Financial Concerns

After the Battle of Long Island, all of New York and the American Army anxiously expected the British to launch an immediate invasion preceded by shelling. The invasion happened, but not until nineteen days after the American defeat on Long Island. After the battle, a quick rearrangement of Wadsworth’s Brigade left Colonel Douglas in charge of his own brigade of three Connecticut Militia Regiments. So too Connecticut commander, Colonel Silliman of Wadsworth’s Brigade, commanded his own brigade of Connecticut militiamen. During this time Douglas wrote to his wife, September 7^th, of his failing health and strained personal financial investments for his own regiment: “at and about Harlem, commanded by Genl Spencer, which is the Division that I belong to, and is called the Center Division. I have three Regts of militia in my Brigade and they give me much fatigue and trouble. Col’s Cook, Pettibone, and Talcott are the commanders… [I] think if we will only stand by each other, and not run home like cowards, with god’s blessing, we may keep them off, which is a victory of itself! I have taken unwearied pains with the Militia, and I am afraid it is too much fatigue for me, as my cough is a little increased. But I hope it is only for a short time… My expenses have been so large that my money falls a little short. I was obliged to entirely support the sick of my Regt for some time, but I suppose you have none to spare. I shall make out, but not so well as I could wish…” He wrote this eight days before his regiment was subjected to the greatest shelling yet of the war, and broke and ran for their lives.

Battle of Kip’s Bay – “Are these the men with which I am to defend American?” Washington, September 15, 1776.

Colonel William Douglas, though an able soldier, brave man – proven time and again in two wars, and passionate patriot, his mark on history is most remembered for his brigade’s full flight from the British army at the small hamlet of Kip’s Bay. Their retreat snowballed into a full rout of the American defenses all along the East River resulting in Washington angrily questioning the merit of those was given to fight the war. History was not kind to Douglas, however, as proven by many eyewitnesses to the bombardment that preceded the British and Hessian invasion of Manhattan Island, no man, even the most experienced veteran, could have withstood the severe and brutal shelling of that small stretch of beach the morning of September 15, 1776.

On Sept. 14^th, Colonel Douglas’ brigade of three regiments of six-month state militiamen was posted along the East River north of the city. They had been sent to Turtle Bay and the cove of Kip’s Bay, at the foot of present 34^th street) to secure about 2,500 barrels of flour from storehouses along the river. British ships plied the waters and the brigade remained, lying behind lines, “although they were nothing more than a ditch dug along on the bank of the river, with the dirt thrown out towards the water.” At first light on the morning of Sept. 15^th, the men peered out over the water to five frigates and a bomb ketch anchored within musket shot of the beach. As the sun lifted over the river, it was reported that eighty-four boats (light infantry, reserves, and Col. Donop’s Hessian grenadier and Yaeger riflemen – under Generals Clinton and Cornwallis) were seen pushing out into the river from Newtown Creek, directly across the river on the Long Island side, “… filled with British soldiers… they continued to augment their forces from the Island until they appeared like a large clover field in full bloom…”

By ten o’clock, the invasion was well under way. The frigates opened up with a devastating, hour long bombardment of over 80 guns – some would later claim the worse they would experience in the entire war. Plumb Martin of Douglas’ regiment wrote, “… there came such a peal of thunder from the British shipping that I thought my head would go with the sound…” British General William Howe, Commander-in-Chief said: “The fire of the shipping being so well directed and so incessant, the enemy could not remain in their works, and the descent was made without the least opposition.” It was noted by several British officers that the ordeal the militia were subjected to was something which in similar circumstances veteran troops have been unable to withstand. Martin wrote: “We kept the lines till they were almost levelled upon us, when our officers, seeing we could make no resistance, and no orders coming from any superior officer, and that we must soon be entirely exposed to the rake of the guns, gave the order to leave.”

Douglas later wrote: “I then moved my brigade abreast of them. They lay very quiet until 10 o’clock and by that time they had about 80 of their boats from under Long Island shore full with men which contained about five or six thousand and four transports full ready to come in the second boats.” He goes on to write of his retreat: “got under cover of the smoke of the shipping and then struck to the left of my lines in order to cut me off from a retreat. My left wing gave way which was formed of the militia. I lay myself on the right wing waiting for the boats until Capt. Prentice came to me and told me, if I meant to save myself to leave the lines, for that was the orders on the left and that they had left the lines. I then told my men to make the best of their way as I found I had but about ten left with me. They soon moved out and I then made the best of my way out.” (Johnston Battles Around New York Footnotes # 180,181). Douglas was the last to leave.

Under such a dreadful bombardment and threat of thousands of British and Hessians troops ready to pull ashore, Douglas’ regiment pulled back in mass and with such fright that there was no collecting the brigade to a new position in the field to make a stand. They created a panic that was quickly joined by the rest of Wadsworth’s Brigade that had been stationed south of Turtle Bay from Kip’s Bay down to the city itself. The retreat turned into a rout once the British and German troops landed and pursued the Americans; even after the appearance of General Washington and his futile attempts to stem the tide to turn and fight, men ran, ignoring the General’s pleas to turn and fight. “The very demons of fear and disorder,” says Martin, “seemed to take full possession of all and everything on that day.” All that day, those of the regiments and brigades who had escaped capture gradually made their way northwest to the American defensive line at Harlem Heights.

Douglas wrote to his wife three days later of his brigade’s retreat and his narrow escape from capture: “…. I then told my men to make the best of their way as I found I had but about ten left with me. They soon moved out and I then made the best of my way out…We then had a mile to retreat through as hot a fire as could well be made but they mostly overshot us. The brigade was then in such a scattered poster that I could not collect them and I found the whole army on a retreat. The regulars came up in the rear and gave me several platoons at a time when I had none of my men with me and I was so beat out that they would have had me a prisoner had not I found an officer that was obliged to leave his horse because he could not get him over a fence so as to get out of their way. I found myself gone if I could not ride. I went over the fence and got the horse over whilst they were firing, mounted him and rode off. We halted here at night…”

After Kip’s Bay, New England Soldiers’ Merit Questioned

After the loss on Long Island, where southern troops held back the British, allowing much of the New England troops to escape, and the rout and panic at Kip’s Bay, there was a growing consensus that believed that New England troops were poor soldiers and not “man’ enough to stand and fight; most especially by mid and southern colonies. Washington’s own Adjunct-general, Colonel Thomas Reed, propagated and kept alive such feelings that threatened to unravel the loosely bound patriotism that held the colonial army together. New England officers protested against the “rancor” and “malice” of these assertions, and represented their injurious influence to members of Congress. Washington, finding that the matter was becoming serious, took the occasion to send a special invitation to Colonels Silliman and Douglas, still holding their titles as brigade commanders of Connecticut militia, to dine with him in the latter part of September, when he “disavowed and absolutely disapproved every such piece of conduct” which had been a grievance to these and other Eastern officers. (Johnston footnote 189). Note: Historian Johnston wrote: “Not a few of the militia in Douglas’s brigade were the identical men with whom Oliver Wolcott marched up to meet Burgoyne a year later, and who, under Colonels Cook and Latimer, ‘threw away their lives’ in the decisive action of that campaign, suffering a greater loss than any other two regiments on the field.”

Battle of Harlem Heights, Sept. 16, 1776

British General William Howe had landed approximately 10,000 troops at Kip’s Bay and cut across the island south of Washington’s lines at Harlem Heights to the north. Early the next morning, a probe by the American ranger force under Colonel Thomas Knowlton quickly grew into a heated skirmish with the British chasing the rebels as they drew back to their lines. Washington saw that the British light infantrymen pursuers had pushed beyond their line of support and he proposed to trap them. He sent Knowlton’s men, along with a company of Virginia riflemen under Colonel Andrew Leitch in a flanking motioned to come up from behind. However, before the trap could be sprung, some of the riflemen fired prematurely and the light infantrymen realized their precarious position. As they drew back, Washington sent in more troops to hurry them along, including those from General John Nixon’s New Englanders, Colonel George Weedon’s Virginians, and Douglas’ militia which had been accused of panicking in their hasty retreat from Kip’s Bay. We pick up the narrative from Plumb Martin, “Our regiment was now ordered into the field… we soon came into action with them. The troops engaged, being reinforced by our regiment, kept them still retreating, until they found shelter under the cannon… we remained on the battle ground till nearly sunset, expecting the enemy to attack us again, but they showed no such inclination that day. The men were very much fatigued and faint, having had nothing to eat for forty-eight hours…”

This action proved to be the first time in the war that American forces had marched out onto the field, held their own before mass British arms, and driven their enemy back. On Sept. 18^th, Douglas wrote his wife Hannah briefly of this action the day after the disaster at Kip’s Bay – commenting on those of his regiment killed and wounded: “…on Monday the enemy came on and we gave them a good drubbing. I have not time to give you the particulars of any part of our action. I have lost my major, a prisoner, —One sergeant or more killed and four wounded, —have missing out of my brigade which sustained the whole fire but 8 or 9 as yet. I hope God will be on our side at last. It is memorable that I have lost no more and God be praised for it. Our lines are now good and if they dare come on without their shipping. I hope we shall give them a drubbing. In the utmost haste. From your faithful husband Wm. Douglas.” Several internet articles report that Douglas was wounded during the battle. Others included he had lost his horse. This is incorrect. According to official casualty reports, Douglas’ regiment had four killed and one missing, no officers were wounded. This error may be traced to one of Douglas’ letters to his wife where he speaks of losing his horse during the Kip’s Bay bombardment and retreat and commandeering another horse to escape. By day’s end, the battle lines were drawn between British and Americans and would not change until General Howe loaded a majority of his army on transports and sailed through Hell’s Gate into the Long Island Sound to land in Westchester County, north of Washington, in the hopes of trapping the American Army to the south.

Battle of White Plains, Oct. 28, 1776

Nearly three weeks after the Battle of Harlem Heights proved the Americans determination to hold the line against the British push north, British Commander-in-Chief, General William Howe, decided to try and flank Washington. On October 12^th, he transported his troops through Hells Gate on the East River and landed them in the American rear at Frog’s Neck (Throng’s Neck). Colonel Edward Hand and twenty-five men from the 1^st Pennsylvania staged a determined defense on the only causeway to the mainland. Over four thousand British troops were delayed by this action. Once additional supplies arrived from New York, Howe decided to ship his men further north to Pelham. By now, Washington was well aware of Howe’s intent. At a council of war on the 16^th, it was decided that Colonel Glover’s regiment would be sent to Pelham to block and delay Howe’s advance. Meanwhile, Washington enacted a withdrawal of the main army from Harlem Heights and into Westchester County, towards White Plains. He would leave behind over 2,000 men to garrison Fort Washington as well as maintain the lines at Harlem Heights which now faced a British force under the command of Lord Percy. The main army was on the road north by October 18^th, the same day that Glover’s regiment temporarily halted Howe’s advance in a dogmatic rear action engagement called the Battle of Pelham (or Pells Point).

Howe’s lethargic advance allowed Washington’s army to slip by and entrench themselves at White Plains. On the morning of October 28^th, the British advanced in two columns; the main British force was on the right and the left was mainly composed of Hessian troops. The British right and American left would remain spectators of the ensuing battle as it was fought by the Hessian and British left and the American right.  The Americans chose to send out two divisions to meet the advancing Hessians: Major General Sullivan’s and Major General Spencer’s, in which Douglas State Militia were present as part of Wadsworth’s Brigade – about 2,600 men in all. They would face an equal number of Hessian forces.

The Battle of White Plains was two part – the initial clash of advanced American forces who ultimately retreated back to the defenses, followed by an assault on the far American right on Chatterton Hill. Douglas’ men only saw action during the initial attack on the Hessians. We pick up Plumb Martin’s description their part in the struggle. Douglas had advanced to a stone wall before an orchard when the Hessian forces showed themselves: “There was in our front, about ten rods distant [a rod is 5 ½ yards or in this case 55 yards] an orchard of apple trees… a party of Hessian troops and some English soon took possession of this ground; they would advance so far as just to show themselves above the rising ground, fire, and fall back and reload… our chance upon them was, as soon as they… fired, to aim at the flashes of their guns… We were engaged in this manner for some time, when finding ourselves flanked and in danger of being surrounded, we were compelled to make a hasty retreat from the stone wall. We lost, comparatively speaking, very few at the fence [stone wall]: but when forced to retreat, we lost, in killed and wounded, a considerable number… We fell back a little distance and made a stand; detached parties engaging in almost every direction. We did not come in contact with the enemy again that day, and just at night we fell back to our encampment.”

On October 31^st, three days after the battle and while still at White Plains, Douglas wrote to Hannah describing his role in the action: “…On Monday the enemy advanced to attack us at this place. I was ordered out with my regiment with three others to meet and endeavor to retard their march. We moved on and at about twelve were attacked by their advanced guard. We drove them back but soon after the main body came on and we stood them until they got on our flank and I ordered a retreat. We had a most severe fire to retreat under, ten men to our one, but we came off in good order and very surely fired on our retreat all the way. I lost three dead and five wounded. They cut my regiment off from our main body and got ahead of me but I took advantage of a wood and got clear of them. My regiment has the honour of behaving most nobly. They are now near neighbors; our lines are about half a mile.”

The British would take Chatterton Hill on the American far right, but not pursue any further action that day. For the next two days, the two forces would face each other without further action. A torrential rain fell during this time forcing Howe to postpone any further attack. When he was ready on the 31^st, the fox had already flown; during the night, Washington had drawn his forces back three miles to Castle North and dug in. Howe would remain at White Plains before deciding to head back to New York City and invest the remaining forces at Fort Washington, capturing the garrison and nearly 3,000 rebels, including a vast quantity of arms and supplies. While Washington’s main army turned south into New Jersey to block any movement the British would make towards Philadelphia, he left a portion of his army in New York. Commanded by Major General Charles Lee. Lee’s division was stationed to prevent any movement by British forces towards New England. Douglas’ Regiment remained with Lee’s division and would see no further action, their six-month enlistment ending on December 25^th in which they returned home and the regiment disbanded. Though Douglas’ skills and bravery as a leader of men was proven, and in 1777 he would be given the helm of a Continental Regiment, White Plains would prove to be the last time he would ever lead men in battle.

Colonel of the 6^th Connecticut Continental Regiment and Failing Health

Douglas once more returned home, but his body had been broken, his health in ruins. The harsh invasion of Canada and the rigors of command during the previous year constructing forts and commanding his men through several battles and retreats took their toll. Though poor in health, he would spend just a week at home before once more raising and commanding a regiment. However, this time, his men would not be problematic, undependable, six month enlisted militiamen, but Continental soldiers – regulars trained and well disciplined and enlisted for the entire war. On January 4^th, 1777, Colonel Douglas would command the 6^th Connecticut Regiment of the Continental Army in the “Connecticut Line.”

On January 1, 1777, the Continental Army was once again reorganized, and this time Washington got his wish. There would no longer be temporary enlistments with emphasis on militiamen supplementing the regular force – all enlistments in the army were to last until the end of the war. Douglas immediately and fervently went about recruiting and equipping his regiment, as before, digging into and sapping his own financial worth to see that his men were well outfitted. The strain must have been great on Douglas who continued to pull his regiment together while suffering from failing health. History does not give details as to his ailment, however his cough, lack of voice, fever, etc., indicated he was perhaps so worn down that a virus or consequent infection, ultimately took his life.

The new regiment wintered in the Hudson Valley in Brigadier General Parson’s Brigade under Major General Israel Putnam (Major General Charles Lee having been captured by the British in New Jersey). Among Douglas’ subordinates was an experienced fighter and leader who was commissioned Lt. Colonel and second in command: Lt. Colonel Return Jonathan Meigs. Meigs had accompanied Colonel Benedict Arnold on his excruciating trek through the Maine wilderness. He had been in Lt. Colonel Shelburne’s Additional Continental Regiment. During the failed attack on Quebec, Dec. 31, 1775, he had been captured. He was paroled, but wasn’t exchanged until Feb., 1777, qualifying him to accept the commission in Douglas’ regiment. As the winter faded into spring, so too did Douglas’ health. By May 12^th, when Douglas became severely ill, Meigs took over as temporary commander of the regiment. With his family and friends at his side, Douglas died, age 35, on May 28^th, 1777.  With Douglas’ death, Meigs, on the 28^th, was formerly named the Connecticut 6^th, commander. Already, days before Douglas’ death, Meigs had made his mark, organizing and heading the 6^th Connecticut on one of the most successful and daring raids of the war; the Sag Harbor Raid – May 24, 1777.

Douglas’ death was recorded as a loss to the service for he was a man of faith, character, and personal courage. Prior to his death, to help meet growing costs of maintaining his farm while supplying his regiment, he sold his property in New Haven. He had received payment in continental dollars, a currency that over time, had become virtually worthless. By the time of his passing, most of the fortune he had acquired as a merchant was gone. Upon his death, he still had some lands beside their home which were eventually deeded to his children. His wife Hannah, some years later, would apply and receive the seven years half pay for widows and orphans of soldiers who died while still obtaining their commission. She would eventually receive $3,150, a tidy sum for those days. Hannah, aged 28 at Douglas’ passing, would never remarry and lived another fifty years. Douglas was buried in the Northford Old Cemetery in Northford, New Haven County, Connecticut. A military marker declares that he was Captain 6^th Company, 1^st Regiment (referring to his service with the Northern Army in 1775). Next to him are his wife Hannah, who died on May 22, 1825, age 77 and their son John Douglas, who died on Feb. 20, 1784 at age 9 years. Colonel William Douglas’ epitaph aptly describes him as “A Gentleman of good Abilities, generous Mind & easy Manners: faithful in Business & Friendship: active & brave in Defense of the Rights of his Country and Mankind.” Douglas poured all his qualities into life and liberty and though his life was cut short, he was rewarded by a legacy that will endure the test of time. As a free people, he deserves our thanks.

For Further Reading check out these great books and free previews on Amazon:

Other articles of interest on Revolutionary War Journal:

Lt. John Mansfield of the Connecticut Line: Commanded the Forlorn Hope at the Battle of Yorktown

1776: List of Battles and Skirmishes of the American Revolution in Chronological Order

Hatter to Hero: American Revolution Colonel Return Jonathan Meigs; Battles of Quebec & Stony Point.

Sag Harbor Raid, May 24, 1777 – Highly Successful Special Ops of the American Revolutionary War

American Tragedy: Retreat from Quebec January – June 1776 & The Battle of Three Rivers Resulting in the Loss of Canada.

SOURCE

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Carrington, Henry B. Battles of the American Revolution. 1876: Published by the Author, New York, NY.

Clark, A. H. A Complete Roster of Colonel David Waterbury Jr.’s Regiment of Connecticut Volunteers 1898: Published by A. S. Clark, New York, NY.

Connecticut History: William Douglas: A Colonial Hero’s Sacrifice. https://connecticuthistory.org/william-douglas-a-colonial-heros-sacrifice/

Connecticut Society for the Sons of the Revolution. William Douglas.https://www.connecticutsar.org/william-douglas/

Connecticut Historical Society. Rolls of Connecticut Men in the French and Indian War. Vol 1 1755-1757, Vol. 2 1758-1763. 1903: Published by the Connecticut Historical Society, Hartford, Connecticut.

Douglas Archives. William Douglas, Colonel of the 6^th Regiment, Connecticut.http://www.douglashistory.co.uk/history/williamdouglas11.htm#.XQ4jF-hKg2w

Douglas, William. “Letters Written During the Revolutionary War by Colonel William Douglas to His Wife Covering July 19, 1775 – Dec. 5, 1776”, Thirty-six letters published over several volumes: New York Historical Society Quarterly. Vol 12 (1928) No. 3, Vol 13 (1929) No. 1, 2, 3, Vol 14 (1930) No. 1,2. Published by the Society and issued to members.

Gabriel, Michael P. Major General Richard Montgomery: The Making of an American Hero. 2002: Fairleigh Dickinson Univ. Press, New Jersey.

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.

Johnston, Henry Philips. Connecticut. Adjutant-General’s Office. Record of Service of Connecticut Men in the I. War of the Revolution, II. War of 1812, III. Mexican War. Hartford. 1889: Case, Lockwood & Brainard Co, Hartford, CN.

Johnston, Henry P. Connecticut Military Record 1775-1848 Record of Service of Connecticut Men in the War of the Revolution… 1889: Hartford, Connecticut.

Johnston, Henry P. The Battle of Harlem Heights. 1897: Published for Columbia University by The MacMillan Company, New York, NY.

Johnston, Henry P. The Campaign of 1776 around New York and Brooklyn… 1878: Long Island Historical Society, Brooklyn, NY.

Martin, James “Joseph Plumb” Sullivan. A Narrative of Some of the Adventures, Dangers, and Sufferings of a Revolutionary Soldier… 1830: Glazier, Masters & Co., Hallowell, Maine.

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Ward, George Kemp. Andrew Ward and his descendants, 1597-1910: being a compilation of facts relating to one of the oldest New England families and embracing many families of other names… 1910: A. T. De La Mare Printing & Publishing Company, University of Wisconsin, Madison, Wisconsin.