The settlement of Winchester began as early as 1729, when Quakers such as Abraham Hollingsworth migrated from Pennsylvania traveling the Indian Path, which was later called the Great Wagon Road by the settlers. He and others began to homestead on old Shawnee campgrounds. Tradition holds that the Quakers purchased several tracts on Apple-pie Ridge from the natives, who did not disturb those settlements. The German and Irish were also early settlers in this area. George Washington worked in Winchester as a surveyor.