5 Peaks Challenge: Mission Trails, San Diego

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If you live in San Diego, you’re probably familiar with Cowles Mountain, a popular hiking destination in Mission Trails. This is definitely the most well-known (and most crowded) mission peak trail, but it is far from being the only one. In fact, there are four other peaks you can hike to, and most of them have various trails leading to the peak, giving you even more options to explore. This is why the 5 peaks challenge was initially started.

The Mission of the 5 Peak Challenge

In order to get people to explore the other peaks, and not just the ever-popular Cowles Mountain, the Mission Trails visitor center established the 5 peaks challenge, where people were challenged to climb all 5 peaks, take a picture at the top, and then submit the 5 pictures to earn a pin and certificate. Some people, looking for an even bigger challenge, committed to doing all 5 peaks in one day.

As of June 26, 2020, the 5 peaks challenge has come to an end, as far as submitting pictures and earning a certificate and pin. However, all 5 peaks are still available to hike, and I encourage all families to set out to explore all that Mission Trails has to offer. My oldest son and I completed the peaks challenge in 2019, when he was 7 years old. Some of the hikes, we did just the two of us. Others, we had the whole family and even other families who wanted to join.

In all honestly, I figured the other 4 peaks weren’t going to be worth the trek, since they weren’t as popular as Cowles Mountain, but I promise you that was not the case. We actually enjoyed some of those mission peak trails even more. Some were shorter but steeper, giving us a great workout in a shorter amount of time. They were all challenging, and all awarded us with beautiful sights along the way.

Getting Started

If you’re just starting off with hiking, these peaks are a great place to start. We used these to prepare the kids for the many hikes I wanted to do in Glacier National Park and the Grand Tetons. Download the AllTrails app and start logging your progress! Be sure to check out my recommended hiking gear as well.

Here are the Mission Trails peaks that make up the 5 peaks challenge, and what you should know about each one.

5 Peaks Challenge Hike: Cowles Mountain

The hike up Cowles Mountain is about 3 miles out and back. There are different trail options, but the main trail starts on Golfcrest Dr. There is a small parking lot there, but it fills quickly, so you’ll likely have to park on the street. Luckily, there is a ton of street parking at this mission peak trail.

The hike up Cowles Mountain will take you the highest peak in San Diego: 1592 feet. This is a moderate hike, with fairly steep inclines in the beginning, and switchbacks and you approach the peak. It is also a very popular hike, so you will encounter many other people and dogs on the trail.

Pyles Peak

We did each of these trails on different days, however, it makes sense to do Pyles Peak on the same day as Cowles Mountain since you need to summit Cowles before continuing on to Pyles. From the top of Cowles Mountain, you’ll find the trail to continue on to hike Pyles Peak.

The trail will take you another 1.5 miles to the summit of Pyles Peak. It’s not all uphill though. You’ll have two descents and two ascents before you reach the summit at 1379 feet. By the end of this hike, you’ll have hiked 6 miles, making it the longest hike of the five peaks.

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5 Peaks Challenge Hike: Kwaay Paay Peak

Kwaay Peak trail is only 2.4 miles round trip, but this trail is a steep one and is sure to get that heartrate up. The trailhead to this hike can be found at 1 Father Junipero Serra Trail, San Diego, CA 92119. You’ll park on the street and then find the trailhead with the Kwaay Paay Peak Trail sign. In this relatively short hike, you’ll reach the summit at 1194 feet.

North & South Fortuna

I’m grouping these two 5 peaks challenge hikes together because a lot of the information is the same for both them. We did these on separate days due to time constraints, but if you do them both on the same day, you’ll only have to do the steepest part once- bonus!

The Trailhead for South & North Fortuna

The trailhead to both of these 5 peaks challenge hikes can be found at the East Fortuna Staging Area. You’ll find the trail head for the Spring Canyon Trail. There are a few different trails in this area, and they all seem to meet up at different parts.

We took the Grassland Loop Crossing Trail to the Oak Canyon Trail. I was a little hesitant about this particular hike with all the various trail changes, but there are signs along the way, and cell service (I pulled up a map on All couple of times to verify I was where I needed to be).

When on the Oak Canyon Trail, you’ll be hiking next to a bit of water, and you’ll have a couple of footbridges to cross. From the Oak Canyon Trail, you’ll catch the Fortuna Saddle Trail. This is where things start to get steep. Over the next half mile, you’ll gain 500 feet, walking straight up the steep trail.

As hard as it is going up, it’s equally hard going down, so be careful! There’s loose gravel and it can be slippery. If you do both peaks in one trek, you only need to do this part once. When you get to the top, you’ll see the trail marker directing you to South Fortuna to the left and North Fortuna to the right.

Accessing the Peaks

We did South Fortuna first, which is the lower of the two peaks at an elevation of 1094 feet. Once you stop and enjoy the views there, you can head back the direction you came, but this time, keep going straight to access the North Fortuna summit. The summit of North Fortuna sits at 1291 feet.

If you do both of these summits in one day, you’ll hike just over 7 miles. If you do one at a time, you’ll hike a little over 5 miles roundtrip for North Fortuna and about 5.8 miles roundtrip for South Fortuna.

And that wraps up the 5 peaks challenge!

More Hikes in San Diego

Looking for more great hikes in San Diego? Check out the 3 Sisters Falls hike and the Cedar Creek Falls hike along with the Kitchen Creek Falls hike. And be sure to check out my list of cheap and free things to do in San Diego as well.

Once you’ve worked up an appetite, check out these family-friendly restaurants in San Diego, and don’t forget dessert at one of these fun places!