The Woods Trail starts at a small parking area at the Mt. Umunhum Road turnoff from Hicks Road.
Woods Trail is a continual climb on wooded hillsides for the first 5.2 miles. For about the first 4 miles, this wooded hillside is the east shoulder of Mt. Umunhum. The hillside drops off steeply to the right of the trail. To the left of the trail, the hillside rises steeply to a ridge that forms the east shoulder of Mt. Umunhum. Although the woods are thick, due to the rugged terrain and steep hillsides, there are great views of other ridges and summits, including the summit of Mt. Umunhum. Seasonal streams and a few permanent streams cascade down the hillsides. In the winter, after drenching winter rains, the Woods Trail crosses many streams and waterfalls along the way. Coastal fog is frequent in these mountains and keeps them moist year round. In shaded areas, the trees and rocks are covered with thick bright green moss.
After the first 4 miles, Woods Trail turns north (right), to continue on hillsides of a ridge that connects Mt. El Sombroso to the ridge of Mt. Umunhum and Mt. Thayer. Again, the hillside drops off steeply to the right of the trail, and climbs steeply to the left of the trail. As the trail continues to climb, the woods become somewhat thinner in places, with shorter trees. Great views of Mt. Umunhum, the Quicksilver Park Hills (Capitancillos Ridge), and the East Bay Hills can be seen.
After a little over a mile (about 5.2 miles from the start of the trail), Woods Trail veers left to climb to the top of this ridge that connects Mt. El Sombroso to the Mt. Umunhum/Mt. Thayer ridge. The woods give way to brush and grass, as the Woods Trail reaches the top of this ridge after climbing the ridge for about .7 miles. A short spur trail leads to the summit of Mt. El Sombroso - 2,999 ft., shortly after Woods Trail reaches this ridge top. Woods Trail then runs along this ridge top for its last . 6 miles where it ends at its trail junction with Kennedy Trail
and Limekiln Trail
. Views are awesome along this ridge top. To the right, one can see all of San Jose, East Bay Hills, and Mt. Diablo - 3,848 ft. To the left one can see Mt. Umunhum - 3,488 ft., Mt, Thayer - 3,478 ft., and several ridges of the Santa Cruz Mountains.