SR 20 heads north from the Charlottesville vicinity along Stony Point Road, which parallels the west flank of the Southwest Mountains. The state highway passes the communities of Key West, Eastham, Stony Point, and Rosena. SR 20 enters Orange County and its name changes to Constitution Highway south of Barboursville, which contains the ruins of the namesake estate. The state highway has a short concurrency with US 33 (Spotswood Trail) in which the highways pass under Norfolk Southern Railway's Washington District. SR 20 heads northeast and intersects SR 231 (Blue Ridge Turnpike) north of Somerset. The state highway continues east and closely parallels the railroad through Montpelier Station, which is named for James Madison's estate Montpelier on the south side of the tracks.