Old Rag is a classic Charlottesville hikes, and one of the crown jewels of Shenadoah National Park. Spectacular views and a challenging rock scramble make this a local favorite; be prepared for company, and you may want to start as early as 7am at the trailhead. Use the parking area location to find directions.
We recommend wearing closed-toed shoes, as the rock scramble can lead to scraped toes if you try and rock the Chacos on the trail. If you are attempting the hike in warmer weather, make sure and bring plenty of water, sunscreen, and a snack - you'll be up there for a while, especially if you are part of a big group or are attempting the hike on a popular weekend day.
Hiking Upward has a thorough explanation of the hike, complete with turn-by-turn directions, photos, and elevation gain - check it out before you go. The Google Map spot below is to the parking area - from the parking area, take the Ridge Trail (blue blazes) by the closed gate up, and you're on your way! The lower parking area (200 car capacity), is now the only one open to the public; you'll walk 0.9 miles following SR600 to reach the trailhead and old parking area.