The Battle of White Plains, 1776

October 28, 1776 — Part of the New York and New Jersey Campaign

The Battle of White Plains took place on October 28, 1776. After British forces captured a key position on the west side of White Plains, the Americans were forced to retreat.

General William Howe, Illustration

General William Howe. Image Source: Wikipedia.

Battle of White Plains Summary

The Battle of White Plains took place on October 28, 1776, between the United States of America and Great Britain. After British forces took control of New York City on September 15, General George Washington was forced to move north to Harlem Heights with the Continental Army. British forces, led by General William Howe, attacked on September 16, but the Americans held their ground and won the Battle of Harlem Heights

A month later, Howe tried to flank Washington at Harlem Heights. His plan was to attack Washington from the east and push him out of Harlem Heights to the Hudson River. If that happened, then the Continental Army would be trapped between Howe’s army and the British Navy, which controlled the Hudson. Howe tried on October 12 but was pushed back at Throggs Neck. On October 16, Washington and his officers decided to abandon their positions on Manhattan Island, except Fort Washington, and move north to White Plains. Two days later, on October 18, the British landed at Pell’s Point. This time, American forces were unable to keep the British from landing, but they were able to delay them. A small force of American troops, led by Colonel John Glover, fought bravely, against overwhelming numbers, long enough to force Howe to pause his advance on White Plains. 

Before Trenton, George Washington, 1776, Portrait, Trumbull
George Washington. Image Source: The Metropolitan Museum of Art.

Over the next 10 days, the Americans moved to White Plains while the British slowly advanced in that direction. Once the Continental Army was at White Plains, they dug entrenchments and prepared for the British attack. The American line stretched from Purdy Hill, near the Bronx River, west to Chatterton’s Hill, on the edge of White Plains. At New Rochelle, Howe was joined by around 8,000 Hessian troops under the command of Wilhelm von Knyphausen. Then Howe moved his army to Scarsdale, New York, and prepared to attack Washington.

On October 28, Howe advanced toward White Plains. On his right was General Henry Clinton, and on his left was General Leopold de Heister. At White Plains, Washington commanded the center, General Israel Putnam was on his right, and General William Heath was on his left. 

Howe sent Clinton and de Heister forward. They were engaged and delayed by Americans under the command of Joseph Spencer. The British were able to push forward and Spencer and his men withdrew to the safety of Chatterton’s Hill. American forces on the hill covered Spencer and his men as they retreated. From that point on, the hill was the focal point of the Battle of White Plains.

Washington sent reinforcements to dig entrenchments and prepare for a British attack. After a short break in the fighting, Howe had his artillery open fire on the hill and sent an assault force of around 4,000 men against the Americans. The Americans fought off the first assault, which was against the left side of their lines. However, Hessian troops and British dragoons attacked the right side of the line, which was defended by inexperienced militia. The militia on that side of Chatterton’s Hill panicked and fled, which forced General Alexander McDougall to order a retreat. By 5:00 that afternoon, the battle was over and the British were in control of the hill.

Although sporadic fighting continued over the next week, the Battle of White Plains was essentially over.

Quick Facts About the Battle of White Plains

  • Date Started: The Battle of White Plains was fought on Monday, October 28, 1776.
  • Date Ended: The battle ended on October 28, 1776, although British and American forces remained in the area until November 4–5.
  • Location: It was fought near White Plains, New York.
  • Theater: The Battle of White Plains took place in the Northern Theater of the American Revolutionary War.
  • Campaign: The battle was part of the New York and New Jersey Campaign of 1776–1777. 
  • Who Won: Great Britain won the Battle of White Plains.
  • Fun Fact: Washington Irving’s “Headless Horseman” from the “Legend of Sleepy Hollow” is a Hessian soldier who was killed at the Battle of White Plains.

What Happened at the Battle of White Plains?

When the British army advanced, Washington ordered his men to take action. He sent Joseph Spencer and the 2nd Connecticut Regiment out to meet the British and slow them down. The left wing of the British line was led by Hessians under command of Colonel Johann Rall. Spencer and his men met them at present-day Hartsdale, New York and they exchanged fire. General Henry Clinton and his men moved into position to attack Spencer and threatened his flank, so Spencer ordered his men to fall back. As they moved back toward White Plains, they took cover behind stone walls, stopped to fire on the oncoming British, and then fell back again. Spencer and his men retreated to Chatterton’s Hill, on the west side of White Plains. 

The hill became a critical part of the battlefield because if the British were able to capture it, it would expose the center of Washington’s army to an attack on its right side. Washington took action to fortify it and protect his flank. He sent Colonel Joseph Reed to take command of the hill. Along with Reed, he sent men under the command of Colonel Joseph Haslett, General Alexander McDougall, and artillery under the command of Captain Alexander Hamilton. When the Americans arrived at Chatterton’s Hill, McDougal, the senior officer, took command. Colonel Rufus Putnam and his men dug entrenchments on the hill to provide protection for the defenders. On the hill, William Smallwood and Haslett, along with their men, were at the center of the line. Militia forces were on the right of the line, on the west side of the hill. McDougall and his men were on the east side of the hill and formed the left of the line.

General Alexander McDougall, Illustration
Alexander McDougall. Image Source: New York Public Library Digital Collections.

Howe assembled his army in a wheatfield, in front of the hill, facing the Americans. Howe met with his officers, discussed the situation, and then sent around 4,000 men into position for an attack. The attacking force was made up of Hessians on the left and center, and British on the right. Rall led the attack, from the left. The center was led by Colonel Carl von Donop, and General Alexander Leslie was on the right.

As the British force moved forward, Howe had his artillery open fire and bombarded the hill. The Americans were outgunned, which allowed the enemy to advance. Leslie and his men were the first to reach the hill. They made a bayonet charge up the hill, but McDougall’s men were able to force them back down. A contingent of Hessians followed after Leslie’s men and also failed to take the hill.

By then, the entire, the entire attacking force was in position near the bottom of the hill. Howe has to stop the artillery fire, in order to keep from hitting his own men. Next, Rall and his men attacked the militia on the American right. As they made their way up the hill, British dragoons rode in from behind them — shocking the military and causing them to panic and scatter. 

With the west side of the hill overrun by the British force, McDougall ordered the Americans to retreat. Haslet and his Delaware men — the “Blue Hens” — formed the rear guard and covered the retreat.

Colonel John Glover and his Massachusetts Men were on the east side of the hill, and held the Britsh back, allowing McDougall’s men to safely retreat to White Plains. Hamilton’s artillery also helped keep the British from pushing further toward White Plains.

Alexander Hamilton, Portrait
Alexander Hamilton. Image Source: Google Arts & Culture.

With control of the hill, the British threatened the Americans in White Plains from the west and the south. However, Howe did not take advantage of the situation to attack Washington at White Plains.

On October 30, Howe made plans to attack Washington — but not until the 31st. While Howe waited, a storm moved in. Heavy wind and rains raged for approximately 20 hours. The weather kept Howe from attacking Washington, who used the time to retreat to North Castle.

After Washington pulled out of White Plains, Howe moved in and stayed there for four days.

On November 5 he decided to return to New York and deal with the Americans at Fort Washington. Washington and his men, badly beaten and demoralized, eventually retreated into New Jersey.

Battle of White Plains Significance

The Battle of White Plains is important to the history of the United States because General William Howe did not attack Washington at White Plains, which allowed the Continental Army to — once again — escape and continue the fight. In the months that followed, American morale plunged, and by the end of December, the situation was bleak. It was then that Washington made the bold decision to cross the Delaware River on Christmas Night 1776 and attack the Hessians at Trenton.

Important Facts About the Battle of White Plains

  • Washington had around 14,500 men at White Plains, while Howe had 14,000, however, not all of them were engaged in the battle.
  • 3,100 Americans fought in the battle, and somewhere between 4,000 and 7,500 men from Howe’s army.
  • The Americans suffered around 320 casualties, along with around 230 for the British.
  • Washington made his headquarters at the home of Elijah Miller. Today, the house is a museum and it is on the National Register of Historic Places.
  • Alexander McDougall was a leading member of the Sons of Liberty in New York.
  • After the Battle of White Plains, Washington’s forces moved out of New York, setting the stage for the historic Crossing of the Delaware and the Battle of Trenton.

Military Commanders at the Battle of White Plains

American Forces

British Forces

  • William Howe
  • Alexander Leslie
  • Johann Rall
  • Carl Von Donop
  • Henry Clinton
  • Leopold de Heister

Battle of White Plains Frequently Asked Questions

What is the story behind the Headless Horseman and the Battle of White Plains?

The “Headless Horseman,” also known as the “Galloping Hessian,” is the villain in Washington Irving’s short story, “The Legend of Sleepy Hollow.” The traditional explanation for the Horseman is he is a Hessian soldier who was decapitated by an American cannonball at the Battle of White Plains.

Did Hessian soldiers at the Battle of White Plains file their teeth?

In the film “Sleepy Hollow,” the Hessian who becomes the Headless Horseman files his teeth into sharp points. It appears this was nothing more than a piece of the legend invented for the movie, to make the Horseman more menacing. There is no evidence to support the idea that any Hessian soldiers actually filed their teeth.

Headless Horseman and Ichabod Crane, John Quidor
This 1858 painting by John Quidor depicts the Headless Horseman Pursuing Ichabod Crane. Image Source: Smithsonian American Art Museum.

Battle of White Plains AP US History (APUSH) Study Guide

Use the following links and videos to study the Battle of White Plains and the New York and New Jersey Campaign for the AP US History Exam.

Battle of White Plains APUSH Definition

The definition of the Battle of White Plains for the AP US History exam is a battle fought between the United States of America and Great Britain on October 28, 1778. It took place near White Plains, New York, during the New York and New Jersey Campaign of the American Revolutionary War. Great Britain won the battle.

American History Central Resources and Related Topics

Battle of White Plains Video

This video from the White Plains Public Library provides an overview of the Battle of White Plains.

Learn More About the New York-New Jersey Campaign on American History Central

Bibliography and Suggested Reading

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Citation Information

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  • Article Title The Battle of White Plains, 1776
  • Date October 28, 1776
  • Author
  • Keywords Battle of White Plains, New York and New Jersey Campaign, George Washington, William Howe
  • Website Name American History Central
  • Access Date May 26, 2024
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 27, 2024