Take paved Kennedy Road to the trailhead directly opposite Top of the Hill Road. The climb has three main segments, though most riders climb just the first two. The entire route is on a wide fire road. Most of the surface is packed dirt though in some places it turns rocky.
The trail begins with a flat and downhill section followed by a climb, then another downhill before the real climb begins. Some sections are quite steep. The first segment ends at a very large tree directly in the center of the trail.
Continuing from the tree, the trail alternates moderately steep climbs and a few flatter sections. There is a false summit at the peak of a steep hill, a brief fast descent, and then two very steep pitches in quick succession, one very short and the other longer and more challenging. These have grades above 25% with a rutted trail surface. At the top of the second pitch, the trail flattens as it approaches the Dogmeat intersection (upper Priest Rock Trail
). Most riders descend Dogmeat or head back down Kennedy from this point. This is the meeting/celebration point for the annual Kennedy Turkey Day Ride.
Kennedy Trail continues past Dogmeat to the junction of Limekiln Trail
and Woods Road. This section is like climbing a roller coaster, with some steep downhills followed by even steeper climbs. Two of the hills here rival the last one on the previous section for difficulty. At the end of Kennedy Trail, you can go left to complete the climb up to El Sombroso on Woods Road, and then descend toward Almaden Quicksilver Park at Hicks Road, or you can turn right to descend the Limekiln Trail