Over the last thirty years as hiking, backpacking, climbing, trail-running, and other outdoor activities have become more and more popular, the number of races, challenges, and other activities that package elements from more than one trail have also increased. Some of these challenges have set days, like the Phoenix 7 Summit Challenge; and some of these challenges can last over the course of a year, like my friend Jeff Hester’s Six Pack of Peaks challenge. And, as of November 7, 2015, Mission Trails Regional Park inaugurated San Diego’s own trail challenge, the Five Peak Challenge, which can be completed in a day, or over the course of a year.

The Five Peak Challenge features climbs up Mission Trails Regional Park's five mountains.

As a San Diego county resident, Mission Trails has long been one of my favorite destinations within the county, and as a blogger, has long been a destination that I’ve recommended to locals and visitors alike. With 7,220 acres of open space and over sixty miles of trails, Mission Trails has been the jewel of San Diego hiking since its opening in 1974. In addition to the many recreation opportunities that it provides, including camping and boating, Mission Trails also boasts a world-class interpretive center, and some of the oldest structures within San Diego County. Mission Trails also is home to San Diego’s most popular trail, Cowles Mountain, which ascends the tallest peak in the city of San Diego. Even though I had hiked the trails – and the mountains of Mission Trails for many years, I had not ever really thought of combining the park’s mountains into an informal challenge, and was intrigued to experience what the park and the city had come up with in their formal program. Due to a busy schedule, I wasn’t able to set the time aside to try the challenge until 2016, but in late July, I was able to take a day to attempt (and complete) the 5-Peak Challenge.

By taking the Five Peak Challenge, hikers will experience many different types of terrain in Mission Trails.

What is the Mission Trails 5-Peak Challenge? The Mission Trails 5-Peak Challenge can be accomplished in a day, or over the course of a year. It involves walking, hiking, or trail running up and down the five mountains of Mission Trails Regional Park – Cowles Mountain, Pyles Peak, Kwaay Paay Peak, South Fortuna Mountain, and North Fortuna Mountain, and taking a summit selfie at or near each of these mountains summit markers. Once one has accomplished this task, one can either go in person to the Mission Trails Visitor Center to display their photos, or e-mail the park their photos to obtain their certificate of completion of the 5-Peak Challenge. In short, it is a fun way to make old trails new, get people outside, and get people motivated to both be fit, and appreciate nature.

It is worth noting that all of these mountains have multiple ways to reach their summits, and because of this, in developing the challenge, Mission Trails set forth a specific set of “suggested” routes to complete the challenge. However, having said that I suspect that if you climb all five mountains in the park, as long as you are on approved route (e.g., on trail), you will also have met the requirements for completing the challenge. But, if you are like me and want to play things by the book, in order to complete this challenge, you will need to hike 23.02 miles, and ascend over 6,100 feet of elevation (6,119 feet, to be exact). Fortunately, there is also an approved map from Mission Trails that was released in connection with the challenge which you can view here, which provides insight as to the routes and their various locations around the park.

When I elected to take the challenge in late July, I decided that I would attempt it in one day, for various reasons, but mostly because I felt it was within my abilities, and I wanted a challenge. Obviously, out of the two ways one can do the challenge, the one day route is much harder than doing it over time. Also, if I’m being honest, the one day route leaves little time to admire the trails, and features, as one is focused on completing a task, versus enjoying nature. For me, I had been on all of these trails many times, and while they are all beautiful, my familiarity with them made it easy to go faster on this occasion. Finally, the method below that I describe is but one way to accomplish the challenge – as a matter of fact, the challenge is tailored for individuality – one can sort when they want to do things, in what order, and on what trail. My way is not the best way, but just a way of many to accomplish things.

Pyles Peak, Cowles Mountain, Mission Trails Regional Park

On that day, I set out to do the peaks in the following order: Cowles, Pyles, Kwaay Paay, South Fortuna, North Fortuna. I started with Cowles because out of all the peaks in the challenge, it by far is the most popular (as I mentioned, it is the most popular hike in San Diego) and I wanted to avoid the crowds. Below you’ll find brief route descriptions of each hike, and what one can generally expect on the trails:

South facing summit panorama, South Fortuna Mountain

Cowles Mountain (Elevation 1,592, distance 4.92 miles roundtrip; elevation gain 1,463 feet): For the challenge, Mission Trails suggests that one takes the Eastern Route up Cowles, which is for the most part a fire access road that leaves from the Big Rock Trailhead in Santee, and is very well marked and easy to follow. This route is longer than the more traditional route (described here) and has slightly less people (slightly!) for the duration of the hike. My tip on this is that in order to save some driving time, one can park at the Barker Way Trailhead, which is the start for the Pyles Peak climb, and follow the Barker Way spur trail until it connects with the main Cowles Mountain Trail. From the summit of Cowles Mountain, one can run down (and then back up) to the summit of Cowles along the eastern trail for the same distance and elevation gain as the route requires. From there, on the return, or before, one can also head down to Pyles Peak. The only difference to this variation is that instead of climbing five peaks, one climbs six (Cowles Mountain twice), and one saves some gas in not driving to and from the Big Rock Trailhead.

North facing summit panorama, South Fortuna Mountain

Pyles Peak (Elevation 1,499, distance 5.58 miles roundtrip, elevation gain 1,499 feet) : If one insists on driving from the Big Rock Trailhead to the Barker Way Trailhead, instead of taking the variation I described, the trail leaves from Barker Way, which is a residential neighborhood. The spur Barker Way trail ascends up to the main Cowles Mountain trail, and goes up and past the summit of Cowles Mountain. The junction to the Pyles Peak Trail from Cowles Mountain is down a wooden set of stairs, and is well marked. From there, the trail descends, before curving down and around, and then ascends up to the summit. The best thing that Pyles has to offer in my mind is that once you pass the spur junction from Cowles, there are few people on the actual trail, and great opportunities for solitude to go with the great views.

Kwaay Paay Peak (Elevation 1,194, distance 2.4 miles roundtrip, elevation gain 969 feet): For this challenge, Mission Trails suggests that one takes the spur trail from near the Kumeyaay Lake Campground, which adds a slight amount of distance. The spur trail connects to the main trail up Kwaay Paay Peak (described here) and ascends straight up the peak. In my opinion, the section of trail halfway up the mountain is the steepest in the challenge, and one that requires caution both ascending and descending. This is also a great peak to do third no matter how long one takes to do the challenge, as it provides a three hundred and sixty degree view of the peaks to the North – the Fortunas – and Pyles and Cowles to the South.

North facing summit panorama, North Fortuna Mountain

South Fortuna Mountain (Elevation 1,094, distance 4.74 miles roundtrip, elevation gain 994 feet): At 1,094 feet, South Fortuna Mountain is the “smallest” peak out of all the mountains, and outside of Kwaay Paay, the mountain with the least elevation gain. The suggested route for South Fortuna leaves from the eastern side of the park in Clairemont Mesa, which in my mind is the lesser known half of the park, even though it is equally as spectacular, and is an area that has many interesting features. This route heads over the bridge into this zone, and does require some route-finding to head toward the peak, with most of the elevation gain coming in the last quarter mile.

To complete the Five Peak Challenge, take a selfie next to each summit's marker for submission to the Mission Trails park staff.

North Fortuna Mountain (Elevation 1,291, distance 5.38 miles roundtrip, elevation gain 1,194 feet): North Fortuna Mountain is the larger brother of South Fortuna, and while it is accessible via the Fortuna Saddle, the challenge suggests one departs from the East Fortuna staging area, which is near Highway 52. From the trailhead, the trail heads across the grasslands section of the park, before heading through some of the park’s seasonal riparian terrain, before heading up the second steepest section to the Fortuna Saddle along a fire access road. From the saddle, it is a straight shot to the summit, which provides the satisfaction of a job well done.

Depending on the season, challengers may see lush growth and seasonal wildflowers.

General Tips: As San Diego has a warm climate generally year-round, challengers should always be prepared with plenty of water irrespective of whether they are climbing one peak, or all five at once. All of these peaks have near total sun exposure for the entirety of the hikes, and challengers should also plan accordingly with sunscreen and hats. The only potential break challengers can expect from direct sun coverage is the consistent early morning marine layer that San Diego experiences year-round, which generally dissipates by 10:00-11:00 a.m. Although there is no “bad” time of year to do these hikes, my suggestion for challengers would be to accomplish most of these hikes from January through April, as the temperatures will be cooler, and the park will be greener, with occasional wildflower blooms. To this end, the park experiences high temperatures May through October, which, while not insurmountable, are something to be recognized. Finally, if you bring a dog with you on these hikes, remember to keep them on leash, and to pick up after anything they may leave behind. Although not required, it’s also great trail etiquette to pick up trash if you can, and to also encourage others to stay on trail politely.

One of many great things about the Five Peak Challenge is that it takes challengers around the entirety of Mission Trails Park, which has a number of interesting features, both natural and man-made.

One Day Tips: At twenty three miles plus of total distance, a one-day bid is a lengthy affair but not insurmountable. No matter what season one attempts it, I would recommend leaving early, and being well supplied with water. Although there are opportunities to re-supply along the way, being prepared regarding the routes and supplies goes a long way to being quick. Finally, be respectful to other hikers along the way and share the trail if you are running, and know your limits. While Mission Trails is not remote by any stretch of the imagination, one does not want to become a rescue statistic if one can avoid it.

Social Media/Generalities: The Park asks that challengers tag their photos on social media with “5PeakChallenge”, both so they can provide support, and so other people can gain tips and insight. Overall, even though I had done all these trails before, I had a great time doing it as a one-day challenge, and will definitely be doing the challenge in some form either later this year, or next. In my mind, although “Five Peak Challenge” is a good name, I prefer “Pentathlon of Peaks”. In any event, whether you are a local to San Diego who wants to try this challenge, or a visitor who likes a long distance trail run, I highly encourage you to get outside, and attempt the newest outdoor challenge in Southern California.