Dear Mr. Sherburne,
Thank you for posting your request on History Hub!
We suggest that you contact Washington County Virginia, Scott County Virginia, and the Virginia Department of Historic Resources for information about plat maps and archival road maintenance reports for the road that you seek. You also may wish to search the USGS Virginia topographical maps for the Hiltons quadrangle, especially the 1935 version.
We hope this is helpful. Best of luck with your research!