Winchester sits at the northern end of the Shenandoah Valley, and the corridor stretching south is one of the more rewarding drives on the East Coast. US 340 and US 11 carry you through the heart of the valley — past apple orchards and Civil War roadside markers — as the Blue Ridge rises steadily on your left and Massanutten Mountain fills the middle distance to your right. The valley has been farmed for three centuries and still looks it: a patchwork of fields, family orchards, and small downtowns that survived because they never mattered enough to be demolished and rebuilt.
The towns along the valley each have their own character. Front Royal at the northern gateway is compact and unpretentious, with a downtown slowly filling with restaurants. Luray, about 50 miles south, sits below the Blue Ridge and is the base for Luray Caverns — among the largest and most dramatic cave systems in the eastern United States, with rooms large enough to contain a concert hall and stalactite formations that took millions of years to develop. Harrisonburg further south is a university town with a strong food scene shaped by a large Mennonite farming community. Staunton, near the valley's southern end, has one of the best-preserved Victorian downtowns in Virginia and the Frontier Culture Museum just outside town.
Shenandoah National Park begins roughly 20 miles south of Winchester, where the Blue Ridge steepens into a long ridge running 80 miles to the south. The Skyline Drive follows the crest the entire length of the park, passing more than 70 overlooks with views east to the Piedmont and west across the valley. Hiking ranges from easy waterfall walks to strenuous ridge climbs; the park has over 500 miles of trails. In autumn, the oak-hickory forest turns red and gold and the overlooks are at their finest. Spring brings wildflowers and migrating warblers.
Wineries have spread across the valley and the Blue Ridge foothills over the past two decades. The wine is genuinely worth stopping for. Pair a winery visit with a stop at one of the valley's farm markets — apple cider, apple butter, and the local apple varieties you will not find in city supermarkets are good reasons on their own to make the drive.