The history of South Mountain defines the early history of western Maryland. It was viewed as a boundary to the Susquehannock in their original treaty granting land to Maryland. In a 1732 letter to the colonial governor of Maryland, Captain Civility (Togotolisa) chief of Conestoga warns against settlement in the valley beyond the mountain. The first Euromerican land grant west of South Mountain by Maryland was William Park's "Park Hall" in 1731 near Crampton's gap. The earliest route of the Great Wagon Road crossed South Mountain by Fox's Gap on a course between Middletown and Sharpsburg. Other important passes for migration and settlement were Turner's Gap near Boonsboro. Orr's Gap, used today by Interstate 70, and the course of "Cartledge's Old Road" generally following Maryland state route 77. Maryland finally gained clear title to the lands west of South Mountain at the 1744 Treaty of Lancaster. Following the 1859 John Brown's Raid on Harpers Ferry seven of the raiders escaped from the Kennedy Farm headquarters to Pennsylvania by following (Elk ridge and) South Mountain north. The escapees traveled by night and spent the days in cold camps among the densest thickets they could find along the remote ridge top. They finally left the mountain near today's Caledonia State Park between Chambersburg and Gettysburg, Pennsylvania. The Battle of South Mountain was fought on the mountain at Crampton's, Fox and Turner's gaps during the Maryland Campaign of the American Civil War in 1862. In 1863, military engagements of the Gettysburg Campaign on the mountain range included the Fight at Monterey Pass near the Mason–Dixon Line.