It begins by following more of the Jackson River to near Clearwater Park, but then crosses a ridge into a different valley. This is repeated several times until Forks of Waters, where the South Branch Potomac River enters US 220's valley and parallels its final to the state line. Part of the Great Wagon Road branched off near what is present day Roanoke, Virginia, and U.S. Route 220 in Virginia now follows part of this section of the Carolina Road. "The route was improved as a stage road in the early years of the republic. In 1838 it was rebuilt to serve the Pittsylvania, Franklin and Botetourt Turnpike, which served to connect south central Virginia with the Valley." As a U.S. Highway, US 220 was initially part of U.S. Route 311, which split from US 11 at Roanoke and ran south to Aberdeen, North Carolina. This was also part of State Route 33, one of Virginia's original state highways from 1918 (which was numbered 3 until 1923). Other than the US 60 overlap, two other segments date to 1918: part of SR 17 from Covington to Warm Springs, and part of SR 39 (originally 9) from Vanderpool to Monterey. Otherwise the gaps were filled starting in 1922, with the legislative designation of a spur of SR 14 from Clifton Forge south to Eagle Rock, which was numbered State Route 142 in 1923. 1924 saw the beginning of the extension of SR 142 southwest to US 11 at Troutville, and it was also extended along SR 14 east to Longdale Furnace and then north to Millboro Springs. In 1926 it became part of a realignment of SR 17, with that route's former routing to Covington becoming part of new State Route 338. The first piece of State Route 395, which ended up extending from Warm Springs to West Virginia, was also created in 1924 as a spur from SR 39 at Monterey. The entire Covington-West Virginia corridor (SR 395 and part of SR 338) became State Route 800 in 1928 (along with an extension southwest from Covington), and was renumbered State Route 18 in 1933. Also in 1933, the part of SR 17 south of Clifton Forge became State Route 12. US 220 was extended into Virginia in 1935, replacing SR 18 north of Covington, all of SR 12, and all of US 311 in Virginia. US 311 has since been re-extended into the state west of Danville.