Winchester is perfectly placed for exploring beyond its own streets. The Shenandoah Valley stretches south from the city along a corridor that takes in limestone caverns at Luray, historic small towns, apple orchards and vineyards, and the long ridge of Shenandoah National Park with the Skyline Drive running its spine. A half-day gets you to the park; a full day lets you reach Luray Caverns and push on into the valley floor. Spend two days and you can cover the valley from Front Royal to Staunton and back at a comfortable pace.