The Battle of Harlem Heights was fought during the New York and New Jersey campaign of the American Revolutionary War. The action took place on September 16, 1776, in what is now the Morningside Heights area and east into the future Harlem neighborhoods of northwestern Manhattan Island in what is now part of New York City. The Continental Army, under Commander-in-chief General George Washington, Major General Nathanael Greene, and Major General Israel Putnam, totaling around 9,000 men, held a series of high ground positions in upper Manhattan. Immediately opposite was the vanguard of the British Army totaling around 5,000 men under the command of Major General Henry Clinton. The Americans, under Washington, Brigadier General Nathaniel Greene, and Major General Israel Putnam—held a series of high ground positions in upper Manhattan against an attacking British division under the command of Brigadier General Alexander Leslie. British troops made what became a tactical error by sounding a fox hunt bugle call while in pursuit, meant to insult the Continental troops, who were in orderly retreat. This instead infuriated the Americans, who galvanized to hold their ground and rallied for victory. On September 15, after the British landed at Kip's Bay, General William Howe and his army advanced on the east side of Manhattan while the Americans advanced on the west side.

Early on September 16, Washington received reports, which proved to be unfounded, that the British were advancing. Washington, who had been expecting an attack, had ordered a party of 150 men under the command of Lieutenant Colonel Thomas Knowlton to reconnoiter the British lines. Two or three companies of the 2nd Light Infantry Battalion advanced to attack the enemy to their front. When Knowlton realized that the numerically superior British forces were about to turn his flank, he ordered a retreat, which was conducted "without confusion or loss", although perhaps ten men had been lost in the initial skirmish. The British followed in rapid pursuit. Knowlton's party emerged into the open on the edge of the woods overlooking a wide re-entrant known as the Hollow Way, which marked the forward edge of Washington's position. The rangers crossed into the American lines while the pursuing light infantry, on reaching the tree line, paused to reorganize. The sound of their bugle calls, whether calling the skirmishers to regroup or calling for reinforcements, to Washington's Adjutant General Colonel Joseph Reed were reminiscent of a fox hunt, and seemed to him to be intended as an insult. There was little fighting for the next month of the campaign, but Washington moved his army to White Plains in October after hearing that the British were attempting to trap him on Manhattan.