Skyline Drive — Rockfish Gap Entrance

The road ends here — or begins, depending on which way you're heading. Rockfish Gap, where Skyline Drive meets the northern terminus of the Blue Ridge Parkway, sits at the boundary of Albemarle and Augusta counties, accessible from Charlottesville via I-64 and US 250.

This gap has been a crossing point for a long time. The Three Notch'd Road, which passed through here, connected Richmond to the Shenandoah Valley by the 1740s, most likely tracing an older Monacan trail. In 1818, James Monroe, Thomas Jefferson, James Madison, and Chief Justice John Marshall gathered with 24 other dignitaries at the Mountain Top Tavern here and chose Charlottesville as the site of the new University of Virginia. Later, a railroad tunnel cut beneath the gap — the same tunnel Confederate General Stonewall Jackson used to move his foot cavalry during the 1862 Peninsula Campaign.

Now Skyline Drive runs 105 miles north along the Blue Ridge crest to Front Royal, the only road through Shenandoah National Park. The entrance is also where the Appalachian Trail passes through. Three hours to drive the whole thing on a clear day — though that assumes you don't stop at any of the 75 overlooks.