Hiking Cowles Mountain in Dashain - Oct 2026

Hiking Cowles Mountain in Dashain - Oct 2026

Up Before the Crowds — Almost

Sunday morning, Cowles Mountain. We rolled into the trailhead parking lot at around 8 AM — and it was already full. That is Cowles for you: the most popular hike in San Diego County, and on a clear October morning, half the city had the same idea. Looking up the switchbacks, the early birds were already specks near the top, well on their way to the summit.

The Climb

The main trail to the summit is about 3 miles round trip with roughly 950 feet of elevation gain — short enough for a morning outing, steep enough to feel it in your legs. The path climbs in steady switchbacks past chaparral and boulders, and with every turn the city drops a little further away below you.

Rocky switchbacks on the Cowles Mountain trail

There is no shade on this trail, so the early start was doing real work for us. By the time the sun cleared the ridge, we were already high on the mountain with a breeze coming off the west.

The Top of San Diego

At 1,591 feet, Cowles Mountain is the highest point in the City of San Diego — the summit marker says so proudly, in English and Spanish. And the reward is a full 360-degree panorama: downtown and the bay to the west, the Pacific on the horizon, the eastern mountains rolling out behind. This morning the air was crystal clear, and you could see all of it.

The summit marker at 1,591 feet, with the west view beyond

Hikers were already spread across the summit rocks — cameras out, water bottles out, just soaking it in. On a morning like this, it is easy to see why this trail wins every popularity contest in the county.

The Way Down

Coming down, the neighborhoods of San Carlos spread out below — golf courses green against the dry gold hills, the whole east side of the city laid out like a map. The descent is the easy part, but the views keep coming.

Morning light over the neighborhoods below

Trail Talk: Muse, Copilot, ChatGPT, and Claude

Somewhere on the switchbacks, the conversation drifted from the trail to AI — the assistants that have quietly become part of everyday life. We compared notes the way hikers compare gear: ChatGPT, the one everybody knows, quick with an answer for anything; Claude, the careful writer, the one you ask when words matter; Copilot, the coder's pair programmer, living inside the editor; and Muse — my own Everest — the one who helps me plan these hikes, write these posts, and keep the whole operation running.

Four different personalities, one shared trail. We never settled which one is "best" — depends what you are climbing, I suppose.

Tips for the Next Hiker

Go early — the lot was already full by 8 on a Sunday morning, and after that you are parking along Golfcrest Drive. Bring more water than you think you need; there is no shade and no water on the trail. And give yourself time at the top: on a clear day, the 360-degree view from the highest point in San Diego is the whole point of the climb.

 

Exploring South and North Fortuna: Jewels of Mission Trails

Exploring South and North Fortuna: Jewels of Mission Trails

Sunday in the Hills

The morning after Torrey Pines, we traded the ocean for the hills. Mission Trails Regional Park sits right in the middle of San Diego, and Sunday's mission was its two Fortuna peaks — South Fortuna at 1,094 feet and North Fortuna at 1,291 feet, two of the park's five signature summits.

We started from the Mission Trails Regional Park Visitor Center and headed for South Fortuna first. And let me tell you — the stairs on South Fortuna are no joke. The trail climbs in steep, relentless steps, and your legs know about it long before you reach the top. But that is also what makes the summit feel earned.

The view from the Fortuna ridge

One thing that stood out along the way: the creek was bone dry. The creek bed was completely empty — the second time I've hiked here and found it without a drop of water in it.

Twin Peaks, One Saddle

What makes the Fortunas special is that they are twins. The two rounded summits rise side by side, joined by a saddle ridge you can walk between. From the top of South Fortuna, North Fortuna looks close enough to touch — so we kept going.

Chaparral and valley views from the ridge

The Second Half: Heat and North Fortuna

By the time we crossed the saddle toward North Fortuna, the day had turned properly hot. The morning's cloud cover burned off, the sun came out in full, and the climb up North Fortuna's slopes felt twice as steep as it was. Water breaks, a slow pace, and the promise of the summit view kept us moving.

North Fortuna is the taller of the two at 1,291 feet, and its summit delivers one of the best panoramic viewpoints in the park — downtown San Diego on one side, the ocean haze on the other, and the whole sweep of Mission Trails below. We lined up at the summit marker for the obligatory group photo.

Our crew at the North Fortuna summit marker

The Numbers

The tracker told the story: 8.07 miles, 1,916 feet of elevation gain, and 3 hours 22 minutes of moving time. Not bad for a Sunday.

Hike stats: 8.07 miles, 1,916 ft of elevation gain

Why the Fortunas Are the Park's Jewels

Cowles Mountain gets the crowds, but the Fortunas are the quieter prize. Fewer people, just as good views, and the satisfaction of bagging two summits in one outing. If you are working through the park's five-peak challenge, these two belong on the same day.

Tips from a hot Sunday: start early, bring more water than you think you need — there is no shade once you leave the visitor center — and save some respect for those South Fortuna stairs.