Battle of White Plains – October 28, 1776 by Harry Schenawolf

Map - Battle of White Plains
Map – Battle of White Plains

The Americans suffered defeat at the Battle of Long Island on August 27th, 1776, and a third of Washington’s army barely escaped Brooklyn to the city. General Washington and his army were forced to wait anxiously for British General Howe to make the next move. The rebel troops were spread out over Manhattan Island, north to Westchester County, and across the Hudson in New Jersey. Not since the Spanish Armada had a gathering of war ships and troops been assembled to defeat a defiant people. A forest of British masts filled New York Harbor. They could easily transport the most professional army of its time to strike at any point along Manhattan and New Jersey’s shoreline. Washington knew his position was untenable. However, his hands were tied. Congressmen, nestled in Philadelphia and far from the sound of cannon, heeded the influence of their wealthy brethren in New York City. They refused to allow their general to take the necessary steps to assure the safety of his army and to deprive the enemy their winter accommodations. They denied any move to torch the city. Moreover, they expected their army to defend what General Lee had claimed the previous year was indefensible. But the supreme commander of American forces had no other choice.

After the Battle of Long Island, the Continental Army was re-organized into three divisions. To the south and in the city was General Putnam’s command. General Greene was stationed mid-island but, due to a bout of malaria, he temporarily relinquished command to General Spencer. To the north was General Heath’s division at King’s Bridge and Westchester County. There was also a contingency at Fort Washington. Across the Hudson was positioned General Mercer with what was called the ‘Flying Division.’  Mostly militia from New Jersey and Pennsylvania, they were stationed along the Hudson and were to deploy wherever they were needed the most. A concept in theory only, because when the British opened up their first broadside, the militiamen left their posts in droves without firing a single shot. Before the end of the year, the militia vanished as a fighting unit and men returned to their homes.

The waiting ended on September 15th when General Howe’s troops crossed the East River from Newtown, Long Island and landed three miles north of New York City at Kip’s Bay. British and Hessian mercenaries swarmed ashore and brushed aside the Douglas’ Connecticut militia. General Putnam’s Division, over three thousand men, was trapped in the city. After a desperate sixteen mile march, they made General Spencer’s defensive line at Harlem Heights.  The next day, General Washington saw an opportunity to strike back. Unexpectedly, he launched an attack against the British forces drawn up in front of the Harlem defenses. A spirited fight ensued that almost became a full blown battle except that the Americans drew back their forces. The Battle of Harlem Heights was not a decisive battle, but it was the first time that rebel forces stood toe to toe with their adversary and drove them back. It also gave the American forces a boost in moral that was desperately needed.

Both armies sat facing each other in their respective entrenched and fortified positions. General Howe was not about to throw his forces against the strong fortifications Washington enjoyed on Harlem Heights. He remained inactive for twenty-six days while setting his plans in motion. As on Long Island, he preferred to flank his opponent. On the evening of October 12th, 1776, he sent a fleet of eighty sail including transports lined with British and Hessian troops. They navigated through Hells Gate and into Long Island Sound. Howe left Lord Percy with three brigades to man the lines facing Harlem Heights. The objective was sixteen miles up the coast to Throg’s Neck in Westchester County. Howe planned to position his army behind the rebels then cut across the county to the Hudson thereby boxing them in. However, unexpected delays were to work to the rebels’ advantage.

The British landed on the 13th at Throg’s Neck (At the time it was called Frog’s Point. The land was owned by a Mr. Throckmorton and eventually became Throck’s Neck changed to Throg’s). It was a marshy section of land that reached out into the sound. Throg’s Neck was not really a peninsula, but an island that tapered to a causeway over a creek and mire that connected it to the mainland. Colonel Edward Hand and a small detachment of riflemen pulled up the causeway’s planks and positioned themselves behind stacks of cordwood. When the advance guard of the enemy approached, Hand’s riflemen opened up with a deadly and accurate fire. Twenty five rebels held back Howe’s entire army until Hand was reinforced with Continental regiments from Massachusetts and New York, nearly 1,800 men. Both sides dug in. Howe remained there for six days while baggage and supplies were brought up from New York. October 18th, the day Washington’s main army began its trek north, Howe withdrew from Throg’s Neck to a more suitable landing on the mainland at Pell’s Point, only three miles further east along the coast. Here he met Colonel Glover who commanded four regiments numbering only 750 men. The rebels put up a smart fire, retreating from stone wall to stone wall and delaying the British until nightfall. As night set, Glover pulled back three miles to rest his troops. The next day, October 19th, had Howe sent his light infantry and grenadiers by straight road to King’s Bridge, they would have caught the American army in column and quite possibly routed the entire army. Instead, Howe remained at New Rochelle for three days before moving to Mamaroneck, only three miles distant. There he stayed for four more days until marching towards White Plains. He camped his forces in Scarsdale, three miles south of White Plains, and established his headquarters at the Griffin House on Mamaroneck Road.

Some years later the British historian Trevelyan expressed the frustration of many of Howe’s subordinates when he wrote, “The sun had set and risen more than forty times since General Howe broke up his summer cantonments on Staten Island. In seven weeks – with an irresistible army and a fleet which there was nothing to resist – he had traversed, from point to point, a distance of exactly thirty-five miles.


Washington had reorganized his army after the Battle of Harlem Heights. This time instead of three divisions, there were now seven. Charles Lee was back with the army after his success in Charlestown, South Carolina. Generals Sullivan and Stirling had also returned. Both men had been captured at the Battle of Long Island and had been exchanged; Sullivan was released from captivity in exchange for General Richard Prescott who was taken in Montreal by Montgomery, and Stirling was given his freedom in trade for Montfort Browne, former royal governor of West Florida. The seven divisions were under the command of Generals Greene, Sullivan, Lee, Heath, Putnam, Spencer, and Benjamin Lincoln. Greene was to hold Fort Lee (renamed from Constitution in honor of the respected general) in New Jersey, across from Fort Washington, with 3,500 men. Another 1,500 men were left in Fort Washington, leaving 14,500 men with Washington. He would keep ten thousand in Harlem and positioned the rest at the floating bridge in King’s Bridge and Westchester County.

When Howe’s attempt to cut across Westchester County was stalled at Throg’s Neck, Washington was given the time to organize a retreat north. On the 16th, a council of war was assembled at the Morris House, Washington’s headquarters in Harlem Heights. It was decided that the army would withdraw as far as White Plains. The main army marched on October 18th, the day Colonel Glover’s brigade halted Howe’s advance from Pell’s Point. On October 20th, two days after Glover’s swift action and what became known as the Battle of Pelham Bay, Washington sent his chief engineer, Colonel Rufus Putnam, the thirty-eight year old distant nephew of General Israel Putnam, north towards White Plains to report on the terrain and General Howe’s movements. Putnam realized that, if the British gained White Plains, General Howe could easily rendezvous with his brother Lord Howe, whose vessels were at Tarrytown on the Hudson. If that happened, then the Continental Army would be encircled. Putnam galloped the ten miles back to Valentine’s Hill to inform Washington, who remained at his headquarters along with the main army. Along the route he met General Stirling who was in the advance column and informed him of the situation.  Washington, upon hearing the news, ordered General Stirling north with all haste to seize and hold the high ground at White Plains until the main army arrived.

The council decided to leave 2,000 men at Fort Washington. Congress had resolved on October 11th that Washington should act to obstruct British ships from navigating the North River beyond the two forts. This meant that the sunken hulks acting as ‘chevaux-de-frise’ be maintained, even though the British had already proven that they could sail beyond the forts at will. To continue the forlorn attempt to stop British shipping meant that both forts needed to be garrisoned. This was ardently supported by General Greene who maintained that the army needed a foothold on Manhattan to preserve a line of communication with New England. Colonel Robert Magaw, commander of the fort, was convinced he could defend it against the British until December if necessary. If needed, the garrison could readily evacuate across the Hudson to Fort Constitution (renamed Fort Lee). As soon as the main army departed, the men at Fort Washington and those left manning the entrenchments before Lord Percy’s forces were soon surrounded, fifteen miles from any support by Washington. Few military decisions were more ill fated.

Chatterton Hill
Chatterton Hill

Troop placements:

The main Continental army arrived on October 22nd. Washington set his headquarters at the Elijah Miller House, a 600 acre farm two miles north of White Plains which was owned by one of Washington’s old comrades from the French and Indian War and who had died of fever in camp in the previous August. He selected a series of hills that overlooked the village of White Plains and all approaches from the south. The name White Plains was derived from the Native American tribe the Wappinger of the Mohawk nation, which called the region Quarropas, meaning “white marshes.” This name was most likely given because of the heavy mist and fog that hovered over the swamplands that stretched out from the Bronx River. Putnam’s division made up the American right on Purdy Hill overlooking a narrow valley down to the Bronx River. Heath’s division occupied Hatfield Hill on the left that bordered swampland. Washington held the center behind the village. Two lines of entrenchments were dug in a shallow curve from the east shore of the Bronx River on the right to a millpond on the far left, three miles in all. The land was hard packed soil and ledges and did not lend well to deep entrenchments. Major Benjamin Tallmadge wrote that “… breastworks were improvised… cornstalks pulled from the fields were stacked with the clods of earth on the bottoms facing the enemy, quickly creating defenses that looked much stronger than they were.”

The ends of both lines were drawn back to secure each flank from attack. Half mile to the right and east of the American line across the narrow valley and steam of the Bronx River, lay Chatterton Hill. It was a ridge about three quarters of a mile long running north and south and 180 feet above the river which dominated all of the White Plains. The gently rounded top was crisscrossed by stone walls between cultivated fields. History notes that General Lee had pointed out the need to heavily fortify Chatterton Hill; for, if it fell into British hands, the American lines would be compromised. Washington partially followed Lee’s advice by sending two militia regiments from General Lincoln’s Massachusetts brigade. Washington’s tired and drawn out army would be given six days to fortify before a sluggish Howe drew up his forces to offer battle.

The day General Howe’s forces landed at Pell’s Point, one hundred and twenty sail arrived in New York Harbor. Aboard were the second grand division of German mercenaries; 4,000 Hessians, 670 Waldeckers, and a company of Jagers. Lieutenant General Wilhelm von Knyphausen was in command. Included were 3,400 British recruits and several Dutch horse transports conveying the Queen’s 16th Dragoons under the command of Lord Hartcourt. The Germans and dragoons were immediately ordered to New Rochelle. This brought the number of troops under General Howe’s command to roughly 13,000 men; basically, equal to the numbers he faced under Washington’s command. The morning of October 28th, ten days after landing at Pell’s Point, Howe ordered his forces to White Plains. Washington was not about to give General Howe the definitive battle he sought on a field of honor. For the illustrious Virginian, if the British were intent on subjecting the colonists to their rule, they would have to smash their forces upon his troops entrenched in a strong defensive stance.

The Battle:

“The sun shown bright, their arms glittered, and perhaps troops never were shown to more advantage than these now appeared,” wrote General Heath of the approaching British. They came on in two columns, thirteen thousand strong. The British comprised the right column commanded by General Clinton. The left were Hessians, under the leadership of General Heister. They crossed the plain heading forward as if they were about to grant Washington his wish and make a direct attack upon his works. General Heath goes on to report that, while on horseback, viewing the approaching British with Generals Washington and Lee, afterwards at Headquarters Washington turned to his generals and said, “Gentlemen, you will repair to your respective posts,” adding, “and do the best you can.” With that the Americans accepted the challenge.

General Spencer, accompanied by six New England regiments from Lee’s division, (including Silliman, Douglas, and Chester at 1,550 strong), was ordered out across the Bronx River to meet the British vanguard. They positioned themselves behind stone walls a mile and a half below the American lines. They waited until the advanced columns were nearly upon them before they released a volley against Heister’s column, throwing them back. Colonel Rall’s regiment of Hessians was about to flank Spencer’s left when he drew back his forces, stubbornly fighting from wall to wall, each time nearly flanked. Gradually Spencer’s men were pushed back until overwhelmed by increasing numbers, and a general retreat was ordered.

Washington, seeing Spencer’s troops pushed back and the Hessians rallying along the Bronx River near the base of Chatterton Hill, ordered Colonel Haslet’s Delaware regiment to reinforce the militia, and the two Massachusetts regiments under Colonels Brooke and Graham were commanded by the chief engineer Colonel Rufus Putnam.

Because Washington could not be certain where the British would attack, he waited a short time before sending additional reinforcements. General Alexander McDougall’s brigade was ordered across the Bronx River to Chatterton Hill as additional support. By the time Haslet’s Delaware regiment made the top of the hill, English artillery had opened up on the summit. Nearly twenty guns were positioned south on a series of small rises. One shot severely wounded a militiaman in the thigh. Blood squirted upwards like a roman candle as the man shrieked in pain. For green militiamen who were already shaken severely by the cannonade, witnessing such violence was too much. Putnam’s entire regiment broke and fled. It was with great effort that Haslet’s troops were able to regroup many of the men and drive them back to their post. Shortly afterwards, McDougal’s brigade arrived. General McDougall’s brigade was made up of the First New York, McDougal’s own regiment, Colonel Ritzema’s Third New York, Colonel Webb’s Connecticut regiment, the remains of Smallwood’s Marylanders after their mauling on Long Island, and two fieldpieces lead by Captain Alexander Hamilton. Including the militia, they numbered 1,600 men in all. General McDougal, senior officer on the field, took overall command. Upon Haslet’s advice, the two militia regiments were stationed on the right behind a stone wall. Smallwood and Haslet held the center in the open, while the rest of McDougal’s forces extended to the left.

Spencer’s forces, in full retreat drove across the Bronx River with Colonel Rall’s forces a musket shot behind. Major Benjamin Tallmadge’s regiment was one of the last to cross. He wrote, “I, being in the rear, and mounted on horseback, endeavored to hasten the last of our troops, the Hessians being then within musket shot… When I reached the bank of the river…. [sprang] headlong into the river… by the time I reached the opposite bank, the Hessian troops were about to enter it and consider me their prisoner.” McDougall ordered his men to fire towards the Hessians who reformed on a small rise near the base of the hill on the American right.

At this point in the initial stages of the battle, the entire British army was drawn up on the field before the American line and halted while its major generals counseled in a wheat field. It was quite the spectacle as stated by an officer in Webb’s regiment, “Its appearance was truly magnificent. A bright autumnal sun shed its luster on the polished arms; and the rich array of dress and military equipage gave an imposing grandeur… in all the pomp and circumstance of war.” After a brief council, a large British detachment of eight regiments, 4,000 men, separated from the main body and headed directly for Chatterton Hill.The rest of the British army, nearly 10,000 strong, sat on their arms as if an audience in observance of the day’s unfolding events.

The Hessians, supported by a brigade of British, found the river unusually high because of recent rains and halted by the bank.  The Germans began felling trees and dragging fences to build a rough bridge. McDougal, noting the British line stalled, ordered the regulars midway down the hill along with one artillery piece. They immediately opened up a sharp fire on the Hessians. General Leslie, commanding the British brigade that was supporting the Hessians, was frustrated and sent runners to seek a ford. One was reported to him a short ways downstream. Leslie ordered the 28th and 35th to the river crossing and led them across. He reformed his men on the other side and directly ordered a bayonet charge up the hill. The regulars poured a hot fire down the slopes, assisted by artillery. Because of the steep incline and thick woods as well as constant musketry, the attackers were forced back upon the 5th and 49th regiments including the Hessians who by then had crossed the river and were rushing in support.

The entire British and Hessian force reassembled and formed two columns. They marched north along the base of Chatterton Hill then turned and formed in line parallel to the Americans. They immediately resumed the attack in full force. Haslet’s Delaware regiment, the Marylanders, and New Yorkers held their ground and met the attack. A detachment of light infantry tried to turn the American’s left, but Webb’s Connecticut regulars came up and drove them back. The British artillery, fearing of hitting their own men who had advanced far up the hill, were soon silenced. General Howe ordered an attack from another sector. Rall’s Hessians, who had forced back Spencer’s corps were sent into action once more.

As stated, Rall’s men had stationed themselves along the base of Chatterton Hill on the rebel right and were unobserved by the Americans. They charged up the hill and surprised the Massachusetts militia regiments under Brooks and Graham. The men turned to the enemy, surged forward and fired a strong volley. But once more, men who just weeks before had been haying their fields, had never come under fire until this day. They found themselves in a horrendous situation that was beyond comprehension. Kettledrums pounding, oboes whining, trumpets blaring, horses hoofs pounding as the Queens 16th Light Dragoons under Lord Hartcourt made the field, bayonets flashing, and saber slicing through the air – all of it was too much. The terrified militia fled in a panic. While the dragoons chased down the militia, their rout left the regular regiments unsupported.

The Marylanders fought desperately. Their commander Smallwood was twice wounded and his regiment became disorganized. Rizema’s New Yorkers also fought fiercely, but the onslaught was too much. McDougall saw there was no hope to hold the hill and drew the Maryland and New York forces back to a road leading to the American camp. There he positioned his men to protect the withdrawal of Haslet’s Delaware troops who were deserted upon the field.

Haslet also pulled his men back, but Rall’s Hessians fell viciously upon them. Three Delaware companies broke and were driven from the field. Haslet held the rest and lined them up behind a fence. Twice his men repulsed the enemy’s charge. By that time the dragoons had returned from chasing the militia. Haslet saw that they were reforming for a charge. After a quick look around he realized that he and his men were alone as the rest of the enemy advanced up the hill. He ordered a hasty retreat, but did so in an organized and deliberate fashion, returning the enemy fire. There was no other action on any other fronts that day.


Each side suffered similar losses in killed, wounded, and captured. The details varied so much between texts and firsthand accounts; Howe had the habit of underestimating his loses, exaggerating rebel losses and rarely listing Hessian losses. American losses were no more than 300 killed, wounded and missing with around 45 killed. The British losses were no more than 313 killed, wounded and missing with around 50 killed. Historians have considered the contest to be a draw.

That evening the British retained Chatterton Hill in full view of the American lines to the east. The Hessian grenadiers were ordered forward within cannon shot of the entrenchments. The second brigade of the British formed on their rear and the two Hessian brigades were stationed to the left of the British second. The center and right of the British line did not quit the ground upon which they had formed that day. Washington, assuming an attack at any moment, strengthened his right. However, the British army was content to lay upon their arms during the night expecting to attack the rebel camp the next day. Interestingly, a terrific rain began to fall that night and all the next day, postponing any plans for an attack. Howe decided to wait until Lord Percy sent the reinforcements he requested. Finally, October 31st, Howe believed he was properly strengthened to make an attack upon Washington’s breastworks when he discovered the old fox and slipped away once more. Washington drew back his forces three miles to Castle North the night before and threw up entrenchments. This was a strong position for his men were on higher ground with the Croton River on their left, leaving it impossible for General Clinton to flank the Americans. Howe did not want to chance a direct attack. He decided to return to New York and assess the situation, focusing on erasing any rebel presence on Manhattan and considering winter quarters. Washington, fearing that his adversary may make an attempt to capture Philadelphia, hastened his troops north, crossed the Hudson, and marched into New Jersey. He took four thousand troops with him leaving the rest with Generals Heath and Lee to form a barrier between the British forces in New York and New England. This set the stage for the disastrous loss of Fort Washington and desperate flight across New Jersey to Trenton.

Author’s Notes

New York artillery commanded by Captain Alexander Hamilton:  Historians either disagree or omit the effectiveness of Hamilton’s artillery. A scan of the web will offer countless examples of laurels placed on the heads of Hamilton’s gun crews. Several recent books written by respected historians echo this, however many older texts give Hamilton’s contribution a mere mention; several failing to even comment on the American artillery on Chatterton Hill. Colonel Haslet, who led the renowned Delaware regiment and was present throughout the action on Chatterton Hill, was dismayed by the decrepit condition of the American artillery. He afterward wrote, “…so poorly appointed, [artillery] that myself was forced to assist in dragging it along the rear of the regiment. While so employed, a cannon-ball struck the carriage and scattered the shot about, a wad of tow blazing in the middle. The artillerymen fled. One alone was prevailed upon to tread out the blaze and collect the shot. The few that returned made not more than two discharges, when they retreated with the field-piece.”  Schecter, in the Battle for New York, states both that Hamilton artillery corps helped to drive off the Hessians from Chatterton Hill and follows it up with Haslet’s first hand frustration. He himself states his regiment were the ones to remove one of the New York cannon from the field. So what to believe? I think Schecter’s approach, by accepting some form of both, may be the answer. The smoke, confusion, fog of battle, all of it lends to its share of frustration and controversy. The artillery may have done its fair share until a well placed cannon shot drove the crew back, forcing Haslet’s aide. Perhaps one crew was poorly manned and Hamilton expertly oversaw the use of the other.

Contradictions by researchers & Web:  I discover many errors and misinformation while researching through texts both old and modern, especially on the web. By closely checking the given facts with each text made available to me including Troop Registration Lists, I tried to put to rest these discrepancies. Most errors were concerned with troop commands, which regiments and brigades saw action, placement on the field, and the order of events prior to and during the battle. Thank you.

Read the first installment of A Black Man’s Destiny (Shades of Liberty) here.


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