The Rockaway Foot Path was an old route across western Long Island that passed through Jamaica Pass, a low opening in the wooded ridge running across what is now Brooklyn and Queens. In 1776 the pass mattered because General George Washington’s defenses faced the main British landing areas but could not guard every road equally. American commanders placed troops along the heights, yet the eastern approach through Jamaica was lightly held and depended on patrols and local knowledge rather than a strong permanent position.

During the night of August 26–27, British commander William Howe sent a large flanking column on a concealed march toward the pass. British officers detained the local tavern keeper William Howard and his son and compelled them to guide the troops along the Rockaway route. The column moved in darkness, reached Jamaica Pass without meeting an effective American guard, and then turned west behind the principal Patriot positions. The maneuver was the operational key to the Battle of Long Island.

At daybreak the British advance struck American forces from an unexpected direction while other British and Hessian units attacked from the front. The result was confusion, encirclement, and heavy American losses, particularly among troops fighting near the wooded heights. Many soldiers were killed or captured, although determined resistance delayed the attackers. Washington withdrew the survivors into the fortified lines at Brooklyn Heights and, two nights later, evacuated the army across the East River under cover of darkness and fog.

The use of Jamaica Pass shows how roads, paths, topography, and local information could decide an eighteenth-century battle. Howe’s army did not succeed simply through greater numbers. Its nighttime movement turned the American left and made the existing defensive line untenable. The episode also reveals the precarious situation of civilians such as the Howards, whose knowledge could be seized by whichever armed force controlled their immediate surroundings. Their role became part of the remembered story of the battle.

Modern streets and development have transformed the landscape, but the marker preserves the location’s relationship to the old footpath. It commemorates neither a stand-alone clash nor a building; it marks a route used in a decisive military maneuver. The pass helped Britain win its largest battlefield victory of the New York campaign, while Washington’s successful evacuation preserved the Continental Army. Together those outcomes made August 1776 both a severe American defeat and a lesson in survival, intelligence, and command.