We began our journey near fabled Woodstock, N.Y., which is best known for the 1969 outdoor concert that did not actually occur there. Woodstock, the music festival, was held some 100 kilometers away in the village of Bethel. Nonetheless, Woodstock is an interesting town to visit, with a vibrant arts community, and is a good spot to begin your trek. Driving is the easiest way to get to Woodstock from New York City or Albany. The Overlook Mountain trailhead is just a few kilometers from the center of Woodstock.