On the night of August 26, 1776, a large British column secretly marched toward Jamaica Pass during the Battle of Long Island. Patrols seized innkeeper William Howard and his son and compelled them to guide troops along a little-used route around the pass. At dawn the British emerged behind the American left while other forces attacked from the front. The resulting encirclement routed Patriot defenders and drove survivors toward Brooklyn Heights. The episode showed how local roads, guides, and failures of reconnaissance could decide an entire battle.

On the night of August 26, 1776 a British force of about 14,000 moved in silence along The Kings Highway in a move to encircle the American defenders. The British forced Howard and his son to lead their troops through an obscure trail, still visible in the Cemetery, around the pass to the road leading to Bedford Village. At daybreak on the 27th, the British swept down the road from Bedford to attack the American positions from behind. At the same time, a second force of redcoats and Hessians charged the front of the American line. The Americans were routed and fled back to the safety of Brooklyn Heights.

The event unfolded through local roads, waterways, farms, workshops, houses, and public institutions. Commanders depended on soldiers and militia but also on printers, physicians, laborers, servants, enslaved people, teamsters, sailors, guides, and families. These participants supplied information, shelter, food, transport, and skilled work, often while bearing confiscation, displacement, disease, or violence. A short marker inscription cannot name them all, but the location helps recover the practical systems and human experiences behind larger military and political developments.

The marker anchors this history to a specific landscape even where the original structure or terrain has changed. Visiting the point allows distances, approaches, and neighboring resources to be considered in ways that written summaries alone cannot provide. It also invites comparison between inherited local tradition and the documentary record. The site's continuing importance lies in showing how national outcomes emerged from decisions, labor, conflict, and endurance at particular communities. In broader context, the episode demonstrates that the Revolution and its consequences were assembled through hundreds of local movements and choices. The surviving point gives those relationships a tangible scale. In broader context, the episode demonstrates that the Revolution and its consequences were assembled through hundreds of local movements and choices. The surviving point gives those relationships a tangible scale.