US 17 and US 50 become a divided highway that crosses the Blue Ridge Mountains at Ashby Gap and enters Clarke County. The two highways descend the mountain to their crossing of the Shenandoah River at Berrys. US 17 and US 50 intersect SR 255 (Bishop Meade Road) south of Millwood and US 340 (Lord Fairfax Highway) in the hamlet of Waterloo south of the town of Boyce. The highway's name becomes Millwood Pike on crossing Opequon Creek into Frederick County. Just east of Winchester, US 17 and US 50 intersect US 522 (Front Royal Pike) and ramps to and from northbound I-81. The three U.S. Highways enter the city of Winchester at their half-cloverleaf interchange with southbound I-81. The US routes follow Jubal Early Drive into Winchester, then turn right onto two-lane Millwood Avenue, which crosses CSX's Shenandoah Subdivision at grade before reaching US 17's northern terminus at the intersection of Cameron Street and Gerrard Street at the southern edge of downtown. US 50, US 522, and US 11 head north along one-way Cameron Street to the center of Winchester; southbound US 11 is accessed via Gerrard Street. Signage however indicates US 17's northern terminus is along Cameron Street at Clifford Street.