I’m on a roll with the national parks this year! I knew I wanted to hike on this trip, and I even originally wanted to come to Shenandoah three times. That’s because the list of hikes is insanely long. Skyline Drive is a scenic route that goes through the entire park from north to south and is 105 miles long. Technically from Winchester it’s only about 35 minutes to the northern tip of Shenandoah but the mountain roads are very curvy and it takes time to get through the park.