Dropping from the Allegheny and Appalachian Mountains of West Virginia, US-50 enters Virginia at the northern tip of the Shenandoah Valley, passing through the center of the quietly attractive small city of Winchester.

Continuing east, in short order the road climbs the foothills of the Blue Ridge Mountains and crosses the Shenandoah River, delighting John Denver fans and carrying travelers through the heart of the ultra-wealthy “Hunt Country” of northern Virginia, a rural and unspoiled landscape of small towns, horse farms, and vineyards that’s home to more well-connected millionaires than just about anywhere in the United States.

Approaching the outer suburbs of the nation’s capital, however, US-50 swiftly loses its luster, and while you can follow it through miles of suburban sprawl on both sides of the I-495 Beltway, you might prefer to follow the misleadingly numbered I-66 freeway—which has nothing at all to do with the real Route 66—into the city. US-50’s final approach takes you past the powerful Iwo Jima Memorial, arriving in Washington DC at the Lincoln Memorial.