The Kennedy Trail starts from a small parking area on Kennedy Road. This is in a sparsely populated residential area.
The trail starts off through the woods, behind occasional houses and out-buildings. After a short while, the trail begins to climb a ridge, and climbs continuously until it reaches the ridge top. Although the trail is wooded, the trees are not dense, and all of the heavily populated San Francisco Bay Area can be seen through the trees.
As the trail climbs, the woods give way to brush. About four miles from its trailhead, Kennedy Trail meets the Priest Rock Trail
. At this trail junction, views of the Santa Cruz Mountains emerge to the south.
After passing the Priest Rock Trail
, Kennedy Trail continues through brush along the ridge top. The continual climb is over, as the Kennedy Trail descends for a short ways, and then continues with gradual ascents and descents, following along the top of the ridge. Views are awesome - San Jose and its surrounding countryside all the way to the East Bay Hills can be seen to the left. The rugged Santa Cruz Mountains can be seen to the right.
Ahead lies a high ridge where Kennedy Trail meets the Limekiln Trail
and Woods Trail
as it ends near Mt. El Sombroso (2,999 ft.), 5.5 miles from its trailhead. Once you've enjoyed your journey, retrace your steps to return to the trailhead.
Wooded, brush. Deer.