In Dec 1930 (CTB), VA 29 was extended north 6 more miles as new routing. Also, a second piece of VA 29 was born running from VA 50 (now SR 627) De Jarrette east 4 miles. In June 1931 (CTB), the original piece of VA 29 was extended north 0.90 miles. In July 1932 (CTB), the two pieces of VA 29 were connected. In July 1933, VA 29 was renumbered as VA 14 from De Jarrette to Gloucester CH and US 17 remained from Gloucester to Gloucester Point. Even though there was always a feery across the York River, VA 29 was never assigned to the Yorktown side - only VA 391. The route followed by VA 29: SR 1208 Greate Rd from the York River north; followed current US 17 to Gloucester except it used SR 1216 in Hayes and US 17 Business into Gloucester; VA 14 to Shacklefords; SR 678; VA 14 to St Stephens Church except SR 681 loop at King and Queen CH; SR 721 to De Jarrette except: SR 652 loop west of Salvia; SRs 644/678 south of Sparta; some abandoned loops and SR 734 Old Sparta Rd west of Sparta; abandoned routing from SR 641 Perimeter Rd sharply southwest to SR 627.

VA 29 abrupt southwest turn to VA 50 1932 Caroline County

Original VA 29 1924 Official

VA 29 extended through King and Queen CH 1929 Official

VA 29 extended to nearly Bowling Green 1932 Official

VA 29 #2: appeared in July 1933, replacing part of VA 28 from US 15-29 Culpeper via Jeffersonton to US 15 ALT Warrenton.
Between 1933-36, VA 29 was moved onto Main St all the way in Culpeper, leaving behind SR 685 (Old Rixeyville Rd, West St and William St.
In Oct 1947 (CTB), VA 29 was renumbered as VA 229 from Culpeper to near Jeffersonton, and downgraded to SR 802 from VA 229 to Warrenton. The stated reason for the renumbering was that there were "two route 29s between Culpeper and Warrenton causing much confusion to strangers."

VA 29 Culpeper to Warrenton 1946 Official

VA 229 replaces VA 29 1948 Official