VA 144 southeast of Danville 1928 Official

VA 301 replaces VA 144 1929 Official

VA 301 extended through Danville 1931 Official

In June 1931 (CTB Minutes), VA 301 was extended northwest another 4.35 miles towards Callands, ending in the Pleasant Gap area.
In July 1932 (CTB Minutes), VA 301 was extended 16.35 miles north through Callands to end at today's SR 607 Worlds.
In July 1933, VA 301 was renumbered as VA 41 north of Danville and VA 86 South of Danville.
VA 301 is approximated today: Walter Mill Rd at the NC line; VA 86, College Park Rd/Old Yanceyville Rd and more VA 86; S. Main St into central Danville; VA 293; VA 41 north of Danville except a lot of abandoned loops plus SR 1133 County Ln near Danville; SR 769 Early Rd and SR 816 Late Rd near Callands; SR 969 to Worlds.

VA 301 exended towards Callands 1932 Official

VA 301 exended through Callands 1932 Pittsylvania County

VA 301 replaced by VA 41 and VA 86 1933 Official

VA 301 #2: Created Sept 1940 as a state route extension for US 301 from Petersburg north to Maryland at Dahlgren. This was an overlay with US 1 to Richmond and VA 2 to Bowling Green. From there it was a renumbering of the pieces of VA 207 in the primary system. The CTB noted that Maryland had already approved route 301 and Virginia was doing the same to match, pending AASHO approval.
This was shown explicitly on the Jan 1941 Official and by July 1941 was renumbered as US 301. It is still US 301 except: Broad St/Lombardy St between Belvidere and Chamberlayne in Richmond; SR 695 near Bowling Green; US 301 Business through Bowling Green
I have my doubts whether this was actually posted as VA 301 first.

VA 207 Bowling Green to Maryland 1940 Official

VA 301 replaces VA 207 and heads to Petersburg Jan 1941 Official

US 301 replaces US 301 1941-42 Official