I've attached some scans of a Rupert family history my mother did. William was one of the sons of Joseph and Mary Rupert (originally Ruprecht) who came from Germany in 1844. His brother Criss was my great-grandfather.
The Rupert farm was north of Grayson, on both sides of what is now Ky 1 and 7, running roughly from Barretts Creek (just north of I-64) to Pactolus. My family lives on the 200 acres remaining. If you visit the area, let me know.