Cowles Mountain via Golfcrest
Our pickEvery city has a hill its people climb for the view, and in San Diego it's Cowles Mountain. The summit sits at 1,592 feet, the highest point in the city of San Diego, and the Golfcrest route starts from a street corner in San Carlos, where Golfcrest Drive meets Navajo Road. That's why Cowles Mountain via Golfcrest tops this list: nothing else here matches it for the experience itself or for being one of a kind, and you reach the city's high point on foot, straight from the neighborhood.
The mountain has a little history on its slopes. It's named for George A. Cowles, a rancher and businessman in San Diego County in the 1870s and 1880s. In 1931, about 500 students from what was then San Diego State College painted a 400-foot letter S on its side. The S was covered during World War II, and the repainting tradition ended in the 1970s for environmental reasons.
On paper, the route looks short: 1.5 miles to the top with 950 feet of elevation gain. That gain comes quickly, over loose rock and cut steps with almost no shade. Mission Trails rates it a 3 for difficulty and pitches it at mid-level hikers with proper footwear and water, and that's the right way to think about it. The payoff at the summit is a 360-degree panorama of San Diego County.
Plan the morning around parking and sun. The trailhead lot at Golfcrest is small and fills early, and with so little shade on the climb, an early start makes sense on both counts. Save real time for the descent, too, since loose rock and steps deserve patience on the way down. Dogs can come along on a leash no longer than 8 feet, and everyone needs to stay on authorized trails. Mission Trails posts park gate hours of 8 AM to 5 PM from November through March and 8 AM to 7 PM from April through October.
Then come down and eat. The Trails Eatery on Jackson Drive is about 10 minutes away, and after 950 feet of loose rock and steps, Sin-A-Mon Roll Pancakes count as earned.




