John Collingswood was a Virginia planter who supported the North American Rebellion in the 1770s. When Nathanael Greene organized the Wilderness Walk in the spring of 1780, Collingswood and his family left their plantation and joined him.
Shortly after crossing into South Carolina, a thirteen-year-old Andrew Jackson prevailed upon Collingswood to allow him to join his family's wagon. Over the course of the next two years, as the exiles made the perilous overland journey from the thirteen colonies to the Jefferson settlement, Jackson endeared himself to the Collingswood family, and John Collingswood came to look upon Jackson as a son.
After reaching Jefferson, the Collingswoods and Jackson established a plantation twenty miles north of Arnold. Jackson married Collingswood's daughter Sarah Collingswood, and succeeded to ownership of the Collingswood plantation upon the elder man's death in the early 1790s.