During the Revolutionary War, Henry Wick possessed the largest portion of this area. His farm comprised 1400 acres of timber and open field. The Wick farm and his neighbors' property were considered the ideal location for a winter camp due to the distance from British forces in New York, the amount of timber needed for shelter and firewood for a large army, and the availability of houses for officers (mainly generals and their staff) to quarter. During the winter of 1779–1780, approximately 600 acres of timber in Wick land and about 2000 acres total in Jockey Hollow were cut down by the soldiers to be used for the construction of huts and as firewood.

In December 1779, over 10.000 Continental Army troops encamped for the winter at Jockey Hollow. Soldiers camped at this location until June 1780, during which time they endured some of the harshest conditions of the war, even worse than the Winter at Valley Forge two years before. Twelve men often shared one of over one thousand simple huts built in Jockey Hollow to house the Army. Amazingly, despite the difficult conditions and lack of food, fewer than 100 soldiers died and only one out of ten deserted.

In January 1781, the Pennsylvania Line, then encamped in Jockey Hollow under the command of General Anthony Wayne, mutinied. They supposedly intended to march to Philadelphia to complain to the state legislature. The mutineers reached Princeton, New Jersey, where Pennsylvania's chief executive Joseph Reed and representatives of the Supreme Executive Council of Pennsylvania negotiated with them.