General William Howe

In White Plains

1. Oct 1776
   Battle of Pell's Point(British Commander-in-Chief in North America)

   On October 18, 1776, Colonel John Glover's Marblehead regiment encountered the British landing force at Pell's Point on the Westchester shore. The British had landed 4,000 troops to flank Washington's army; Glover had approximately 750 men in four regiments. What followed was one of the most skillful delaying actions of the entire war. Glover posted his regiments behind stone walls at intervals, ordering each to fire a volley, then fall back to the next position while the next regiment fired. The British advanced cautiously, unable to determine American strength. Glover sustained the action for most of the day, inflicting significant casualties on the larger force while taking relatively light losses himself. The military significance was profound: Glover's delay gave Washington ten critical days to withdraw from Harlem Heights, march to White Plains, choose his position, and construct earthworks before Howe arrived. Without Pell's Point, the British might have cut the American army off before it could reach defensible ground. Glover's action receives little attention in popular histories of the Revolution, but professional military historians consistently identify it as one of the most important small-unit actions of the war.

2. Oct 1776
   Battle of White Plains(British Commander-in-Chief in North America)

   The Battle of White Plains began on October 28, 1776, when British and Hessian forces approached the American lines. Howe's main effort targeted Chatterton Hill, the ridge west of the Bronx River that anchored Washington's right flank. The assault required the British to cross the river under fire from American defenders on the hill, then climb a steep slope against entrenched positions. The fighting on Chatterton Hill was among the most intense of the New York campaign. Alexander McDougall's mixed force of militia and Continentals initially held the British advance. The militia units on the hill's western face broke when Hessian infantry appeared from an unexpected direction, and the Continental regiments, their flanks exposed, were forced to fall back. The entire American force withdrew to the next ridge line in reasonable order — not a rout, but a defeat. Washington's new position on the northern ridge was stronger than Chatterton Hill, and Howe did not immediately assault it. He spent two days massing artillery and preparing what appeared to be a general attack. Then a rainstorm arrived, and he stopped. He never resumed the offensive at White Plains. The decision to halt allowed Washington to withdraw north to North Castle in good order on November 1.

3. Oct 1776
   British Assault on Chatterton Hill(British Commander-in-Chief in North America)

   The assault on Chatterton Hill was the tactical crux of the Battle of White Plains. British artillery opened fire on the American position while infantry and Hessian forces prepared to cross the Bronx River. The crossing was contested — American riflemen on the hill's western slope made the fording difficult — but the British managed it in force. The Hessians climbed the hill's steep face while British regulars pushed from the south and southwest. The American militia on the western face broke when they saw themselves outflanked, and their collapse exposed the Continental regiments beside them. The Continentals — including elements of Smallwood's Maryland regiment — fought harder and fell back in better order, but they could not hold the hill alone once the militia had gone. The loss of Chatterton Hill was significant but not catastrophic. Washington's army still occupied the higher ground to the north, and Howe's possession of Chatterton Hill gave him an artillery position, not a decisive advantage. The decision of what to do next belonged to Howe, and he chose caution.

4. Oct 1776
   Howe Declines to Pursue(British Commander-in-Chief in North America)

   After taking Chatterton Hill on October 28, Howe spent two days massing forces and artillery for what appeared to be a general assault on Washington's new position on the northern ridges. Then a rainstorm arrived on October 30, and the planned attack was postponed. Howe never resumed it. He turned his attention south, toward Fort Washington and the opportunity to capture the garrison Washington had left behind on Manhattan. The decision not to pursue Washington after White Plains is one of the most analyzed choices in the entire New York campaign. Howe's critics, then and since, have argued that a determined pursuit could have destroyed or captured the Continental Army at its most vulnerable point. Howe's defenders argue that attacking a prepared position in rain and mud carried risks that might not have been worth the potential gain. Whatever the reasoning, the consequence was definitive: Washington escaped. He moved north to North Castle, then west to Fort Lee across the Hudson, then south through New Jersey in what became known as the "long retreat" — ending at the Delaware, where the army's crossing on Christmas night 1776 set up the victories at Trenton and Princeton that transformed the war's momentum.

5. Nov 1776
   Washington Retreats to North Castle(British Commander-in-Chief in North America)

   On November 1, 1776, Washington withdrew the main army north from White Plains to North Castle (present-day Armonk), leaving Howe in possession of the White Plains battlefield. The move was orderly and unopposed — Howe was not following. From North Castle, Washington could monitor British movements and decide whether to move further north or cross the Hudson to New Jersey. The decision he faced was genuinely difficult. His army was intact but weakening: enlistments expiring, men deserting, supplies running low. Moving north would put distance between him and the British but would also distance him from the Continental Congress in Philadelphia and from the New Jersey towns that a British advance would threaten. Moving west across the Hudson to New Jersey would mean abandoning Westchester and committing to a campaign in a new theater. He chose New Jersey. The march from North Castle to the Hudson River crossing at Peekskill was the last leg of the retreat that had started at Kip's Bay. When the army crossed the Hudson in early November, it was the end of the New York phase of the war.