The Rockfish Gap Entrance Station to Skyline Drive sits at Mile 105.4, reachable from Exit 99 on I-64. It is the southernmost gateway to Shenandoah National Park and one of the busiest entrances during peak fall foliage season. Three miles to the west sits Waynesboro itself, population around 22,000, tucked against the western foot of the Blue Ridge where the South River drains down out of the mountains. The Appalachian Trail crosses through. Hikers descending from the high country know Waynesboro as the place to resupply, do laundry, and eat something that isn't out of a bag. The town's character is shaped as much by the through-travelers as by its residents.

On March 2, 1865, a small Confederate force under General Jubal Early made its final stand near here against a much larger Union cavalry force commanded by General Philip Sheridan. The Battle of Waynesboro was brief and decisive - Sheridan's troops broke the Confederate line and captured roughly 1,500 prisoners, essentially ending Early's command in the Shenandoah Valley. The war would end weeks later at Appomattox, about 70 miles to the south. Each year, local groups commemorate the battle on its anniversary. The fields where it was fought are now mostly residential neighborhoods and commercial frontage, with markers scattered through town reminding residents and visitors what happened on this otherwise ordinary patch of valley floor.

Summer in Waynesboro fills Ridgeview Park near the center of town. The Summer Extravaganza, held the weekend after the Fourth of July, runs Saturday morning through Sunday evening with live music, carnival rides, magic shows, cloggers, and a Sunday-evening fireworks show. Early October brings the Fall Foliage Festival, timed to catch the Blue Ridge at its peak orange and red. The South River cuts through downtown, and it has become an unlikely urban trout fishery thanks to stocking programs and a Special Regulation Trout Area. On warm afternoons, anglers in chest waders work pools within sight of brick storefronts.

Waynesboro is about a 27-mile drive from Charlottesville and the closest commercial airport, Charlottesville-Albemarle. Amtrak's Cardinal route, running three times a week between New York and Chicago, stops in neighboring Staunton. The town's location near the intersection of I-64 and I-81 - the east-west corridor crossing the Blue Ridge and the long north-south backbone of the Shenandoah Valley - made it a logistics hub a generation ago and keeps it convenient now. (I-64 and I-81 formally intersect at Staunton, eight miles to the west, but the two corridors effectively converge at the edge of Waynesboro.) From a bench downtown you can watch trucks heading west toward the Alleghenies and motorcycles peeling off toward the Parkway. Waynesboro doesn't try to be one thing. It's the kind of place that earns its character from being on the way to somewhere else.