Skyline Drive — Rockfish Gap Entrance

The road ends here — or begins, depending on which direction you're pointed. Rockfish Gap, where Interstate 64 and US Route 250 cross the Blue Ridge Mountains, marks the southern terminus of Skyline Drive and the northern entrance to the Blue Ridge Parkway, the two highways meeting at the ridge. One road continues north through Shenandoah National Park all the way to Front Royal; the other heads south toward North Carolina. The gap sits on the Albemarle-Augusta county line, the boundary between Charlottesville's piedmont and the Shenandoah Valley beyond.

This crossing has weight. In 1818, James Monroe, Thomas Jefferson, James Madison, and Chief Justice John Marshall met at a tavern here and chose Charlottesville as the site for the University of Virginia. The gap was already old by then — Native American trails through it had been widened for colonial wagons by the 1740s, and carriages were crossing by 1782. The road that became US 250 followed those same contours centuries later.

The drive north runs 105 miles along the Blue Ridge crest. Three hours on a clear day, if you don't stop. The deer and black bear don't particularly care about your schedule.