There are at least as many ways to climb Cowles Mountain, the highest elevation within San Diego's city limit, as there are digits on your hand. Perhaps the least popular but no less fun approach is the short but challenging ascent by way of the northwest ridge. It begins with a steep, informal trail best suited for hikers wearing sturdy footwear. Once past the initial rough and rocky section, a newer, well-graded trail, high on the west slope, takes you more or less directly to the summit. The newer trail, carved into the mountain about three years ago, is a great improvement over the primitive ridgeline path previously followed by hikers.
Find a place to park near the corner of Mission Gorge Road and Golfcrest Drive. On the shoulder of Mission Gorge Road, just east of Golfcrest, find the narrow trail that wastes no time in going straight up a ridge to the east. One half mile (and 600 vertical feet) later, you come upon a wider, maintained section of trail. Continue climbing on an easier gradient and pass a side trail going northeast up to the rocky summit of Pyles Peak.
Nearing a saddle just south of Pyles Peak, the trail veers right (south) and maintains a steadily rising, gently curving course high on the west side of the ridge leading to Cowles Mountain. Chaparral-clad slopes fall away on your right to the curving streets and toylike houses of suburbia, which seem to lap at the foot of the mountain. On spring mornings when a low-elevation marine layer blankets the lowland and the suburban sprawl disappears, the distant, rumbling roar of traffic floats up and reminds you of your place amid the city.
When you reach the summit you can either retrace your steps, 3.2 miles for the round trip; or instead, for a longer, roundabout return, follow the main Cowles Mountain trail down the south side to Navajo Road and Golfcrest Drive, then the sidewalk along Golfcrest Drive back to your starting point.