Battle of White Plains The Battle of White Plains was a battle in the New York and New Jersey campaign of the American Revolutionary War fought on October 28 , 1776 , near White Plains , New York . Following the retreat of George Washington ' s Continental Army northward from New York City , British General William Howe landed troops in Westchester County , intending to cut off Washington ' s escape route . Alerted to this move , Washington retreated farther , establishing a position in the village of White Plains but failed to establish firm control over local high ground . Howe ' s troops drove Washington ' s troops from a hill near the village ; following this loss , Washington ordered the Americans to retreat farther north . Later British movements chased Washington across New Jersey and into Pennsylvania . Washington then crossed the Delaware and surprised a brigade of Hessian troops in the December 26 Battle of Trenton . Background . British General William Howe , after evacuating Boston in March 1776 , regrouped in Halifax , Nova Scotia , and embarked in June on a campaign to gain control of New York City . The campaign began with an unopposed landing on Staten Island in early July . British troops made another unopposed landing on Long Island on August 22 , south of the areas where General George Washington ' s Continental Army had organized significant defenses around Brooklyn Heights . After losing the Battle of Long Island on August 27 , General Washington and his army of 9 , 000 troops escaped on the night of August 29 – 30 to York Island ( as Manhattan was then called ) . General Howe followed up with a landing on Manhattan on September 15 , but his advance was checked the next day at Harlem Heights . After an abortive landing at Throg ' s Neck , he landed troops with some resistance at Pell ' s Point on October 18 to begin an encircling maneuver that was intended to trap Washington ' s army between that force , his troops in Manhattan , and the Hudson River , which was dominated by warships of the Royal Navy . Howe established a camp at New Rochelle , but advance elements of his army were near Mamaroneck , only from White Plains , where there was a lightly defended Continental Army supply depot . Prelude . On October 20 , General Washington sent Colonel Rufus Putnam out on a reconnaissance mission from his camp at Harlem Heights . Putnam discovered the general placement of the British troop locations and recognized the danger to the army and its supplies . When he reported this to Washington that evening , Washington immediately dispatched Putnam with orders to Lord Stirling , whose troops were furthest north , to immediately march to White Plains . They arrived at White Plains at 9 am on October 21 , and were followed by other units of the army as the day progressed . Washington decided to withdraw most of the army to White Plains , leaving a garrison of 1 , 200 men under Nathanael Greene to defend Fort Washington on Manhattan . General Howe ' s army advanced slowly , with troops from his center and right moving along the road from New Rochelle to White Plains , while a unit of Loyalists occupied Mamaroneck . The latter was attacked that night by a detachment of Lord Stirling ' s troops under John Haslet , who took more than thirty prisoners as well as supplies , but suffered several killed and 15 wounded . As a result , Howe moved elements of his right wing to occupy Mamaroneck . On October 22 , Howe was reinforced by the landing at New Rochelle of an additional 8 , 000 troops under the command of Wilhelm von Knyphausen . Washington established his headquarters at the Elijah Miller House in North White Plains on October 23 , and chose a defensive position that he fortified with two lines of entrenchments . The trenches were situated on raised terrain , protected on the right by the swampy ground near the Bronx River , with steeper hills further back as a place of retreat . The American defenses were long . Beyond that , on the right , was Chatterton ' s Hill , which commanded the plain over which the British would have to advance . The hill was initially occupied by militia companies numbering several hundred , probably including John Brooks ' Massachusetts militia company . On October 24 and 25 , Howe ' s army moved from New Rochelle to Scarsdale , where they established a camp covering the eastern bank of the Bronx River . This move was apparently made in the hopes of catching Charles Lee ' s column , which had to alter its route toward White Plains and execute a forced march at night to avoid them . Howe remained at Scarsdale until the morning of October 28 , when his forces marched toward White Plains , with British troops on the right under General Henry Clinton , and primarily Hessian troops on the left under General von Heister . Battle . While Washington was inspecting the terrain to determine where it was best to station his troops , messengers alerted him that the British were advancing . Returning to his headquarters , he ordered the 2nd Connecticut Regiment under Joseph Spencer out to slow the British advance , and sent Haslet and the 1st Delaware Regiment , along with Alexander McDougall ' s brigade ( Rudolphus Ritzema ' s 3rd New York Regiment , Charles Webb ' s 19th Continental Regiment , William Smallwood ' s 1st Maryland Regiment , and the 1st New York Regiment and 2nd New York Regiment s ) to reinforce Chatterton Hill . Spencer ' s force crossed the Bronx River , set up behind a stone wall , and exchanged fire with the Hessians led by Colonel Johann Rall that were at the head of the British left column . Eventually forced to retreat when Clinton ' s column threatened their flank , these companies retreated across the Bronx River , while fire from the troops on Chatterton Hill covered their move . Rall ' s troops attempted to gain the hill , but were repelled by fire from Haslet ' s troops and the militia , and retreated to a nearby hilltop on the same side of the river . This concerted defense brought the entire British army , which was maneuvering as if to attack the entire American line , to a stop . While Howe and his command conferred , the Hessian artillery on the left opened fire on the hilltop position , where they succeeded in driving the militia into a panicked retreat . The arrival of McDougall and his brigade helped to rally them , and a defensive line was established , with the militia on the right and the Continentals arrayed along the top of the hill . Howe finally issued orders , and while most of his army waited , a detachment of British and Hessian troops was sent to take the hill . The British attack was organized with Hessian regiments leading the assault . Rall was to charge the American right , while a Hessian battalion under Colonel Carl von Donop ( consisting of the Linsing , Mingerode , Lengereck , and Kochler grenadiers , and Donop ' s own chasseur regiment ) was to attack the center . A British column under General Alexander Leslie ( consisting of the 5th , 28th , 35th , and 49th Foot ) was to attack the right . Donop ' s force either had difficulty crossing the river , or was reluctant to do so , and elements of the British force were the first to cross the river . Rall ' s charge scattered the militia on the American right , leaving the flank of the Maryland and New York regiments exposed as they poured musket fire onto the British attackers , which temporarily halted the British advance . The exposure of their flank caused them to begin a fighting retreat , which progressively forced the remainder of the American line , which had engaged with the other segments of the British force , to give way and retreat . Haslet ' s Delaware regiment , which anchored the American left , provided covering fire while the remaining troops retreated to the north , and were the last to leave the hill . The fighting was intense , and both sides suffered significant casualties before the Continentals made a disciplined retreat . Casualties . John Fortescue ' s " History of the British Army " says that Howe ' s casualties numbered 214 British and 99 Hessians . However , Rodney Atwood points out that Fortescue ' s figure for the Hessians includes the entire Hessian casualties from 19 – 28 October and that in fact only 53 of these casualties were incurred at the Battle of White Plains . This revised figure would give a total of 267 British and Hessians killed , wounded or missing at White Plains . Henry Dawson , on the other hand , gives Howe ' s loss as 47 killed , 182 wounded and 4 missing . The American loss is uncertain . Theodore Savas and J . David Dameron give a range of 150 - 500 killed , wounded and captured . Samuel Roads numbers the casualties of 47 killed and 70 wounded . Henry Dawson estimates 50 killed , 150 wounded and 17 missing for McDougall ' s and Spencer ' s commands but has no information on the losses in Haslet ' s regiment . Aftermath . The two generals remained where they were for two days , while Howe reinforced the position on Chatterton Hill , and Washington organized his army for retreat into the hills . With the arrival of additional Hessian and Waldeck troops under Lord Percy on October 30 , Howe planned to act against the Americans the following day . However , a heavy rain fell the whole next day , and when Howe was finally prepared to act , he awoke to find that Washington had again eluded his grasp . Washington withdrew his army into the hills to the north on the night of October 31 , establishing a camp near North Castle . Howe chose not to follow , instead attempting without success to draw Washington out . On November 5 , he turned his army south to finish evicting Continental Army troops from Manhattan , a task he accomplished with the November 16 Battle of Fort Washington . Washington eventually crossed the Hudson River at Peekskill with most of his army , leaving New England regiments behind to guard supply stores and important river crossings . Later , British movements chased him across New Jersey and into Pennsylvania , and the British established a chain of outposts across New Jersey . Washington , seeing an opportunity for a victory to boost the nation ' s morale , crossed the Delaware and surprised Rall ' s troops in the December 26 Battle of Trenton . Legacy . Each year on or near the anniversary date , the White Plains Historical Society hosts a commemoration of the event at the Jacob Purdy House in White Plains , New York . Two ships in the United States Navy were named for the Battle of White Plains . CVE - 66 was an escort carrier in World War II . AFS - 4 was a combat stores ship that was decommissioned in 1995 after suffering extensive damage in 1992 ' s Typhoon Omar .