The Grayback Mountain Trail is named for Grayback Mountain, the highest peak in Josephine County, Oregon at 7,048 feet. The trail begins from a trailhead south of Williams, Oregon, about two miles up Rock Creek Road (BLM Road 39-5-14). There is a BLM sign and a gravel pullout area where the trail starts. Hikers can shorten the route a little by a mile by driving further to a yellow gate, parking, and walking past the gate to join the trail. Initially, the trail rolls up and down for the first couple of miles before beginning a moderate, steady climb along the southeast side of the ridge through forests of madrones and pines. At about 4,400 feet, long switchbacks provide views of the Williams Creek Valley to the north. The trail continues to traverse the ridge, reaching another set of tight switchbacks. The trail turns southeast and climbs several steeper switchbacks over the east ridge of Big Sugarloaf Peak (6,679 feet), eventually ending at Windy Gap saddle at 6,500 feet. The best views are from the summit of Big Sugarloaf, providing a rewarding experience for those who make the climb. Although the trail does not reach the summit of Grayback Mountain, it offers an almost brush-free, cross-country scramble from Windy Gap to the peak.