Within the city limits of San Diego there is a 7,200 acre park filled with hiking opportunities. Sixty miles of trails are available in Mission Trails Regional Park, but many people will choose to visit only the most popular hike – Cowles Mountain. Sure, the view from San Diego’s highest peak is phenomenal! It’s a must see, but so are the other various trails and peaks in the area. For this reason, the 5 Peak Challenge was born, including the renowned Cowles, but introducing hikers to other fantastic vistas on Pyles Peak, Kwaay Paay, South Fortuna, and North Fortuna where you will also find solitude in nature.
Helpful Tips:
+Looking for glory? Win a certificate and logo pin upon completing the hikes by taking a selfie next to the monument on each summit and emailing them to peakchallenge@mtrp.org with your name. Your dog can win a certificate too!
+Want a map to help plan your route? Check out the park website.
+There are multiple ways to hike up each of these peaks, so you can challenge yourself over and over again.
+Parking is free.
+Pack water, a snack, and wear a hat for a safe and fun experience.
Cowles Mountain – 3 miles roundtrip / 850-foot elevation gain
Everyone wants to conquer the tallest peak in San Diego, so the summit of this mountain is always crowded. The most popular trailhead is Cowles Mountain Staging Area on Golfcrest Drive equipped with restrooms.
A distinctly well marked and dusty trail beings gradually enough, then starts to switchback gaining elevation quickly. 
At the summit you will find many people, antennae, and immensely beautiful views.
Make sure you note where you came from, because there are multiple connecting trails in the area – including the hike to Pyles.
There is a board pointing out additional hikes in the area you may want to take.
Return the way you came.
Pyles Peak – 6 miles / 1,800-foot elevation gain
Cowles and Pyles must be done together – I didn’t realize this when I did Cowles originally, I didn’t even know about the challenge at that point. So I had to resummit, and decided to tackle the mountain from a different trailhead to keep it interesting, on Barker Way. 
I found this less popular route much more peaceful on the way up to Cowles, with a helpful map and welcoming quails on the street.
The trail was easy to follow up to Cowles, and once you summit the first mountain keep your eyes peeled for the small sign that signifies the route to Pyles.
After leaving the busy summit, you will find that the trail here becomes blissfully less populated.
There are some ups and downs enroute, another clear path to follow, and even a spur to a vista along the way. At the splendid summit there was no one to share the view with, what a difference from its nearby neighbor.
Out and back.
Kwaay Paay – 2.4 miles / 875-foot elevation gain
The quickest and easiest of summits to conquer, and likely the least visited, this combination makes for quite the pleasant hike.
Starting down the road from the parking area at the Old Mission Dam, pick up the trail you’ll gain elevation quickly on this short hike.
It can be slippery steep and dusty, so watch your footing as you’re admiring the views. Wildlife was more abundant on this path than the other more frequented mountains.
Many a lizards beneath my feet and hawks above my head made things even more enjoyable.
At the top the views are most exceptional and serene, not another soul around.
Head back on the same path.
South Fortuna – 5.8 miles / 1,500-foot elevation gain
From the Visitors Center Parking head towards San Diego river crossing, there are rocks in place to help you cross during the wet season.
Then take the Suycott Valley trail which will lead you in to the South Fortuna trail.
At the base of the plateau you will see the strenuous nature of what lies ahead.
It is all worth it at the summit, where there are the most stunning views and once again, no one else around.
Hazy silver and blue scenes stretch all the way out past the city and to the bay.
Continuing along past the summit you could connect to North Fortuna or loop back to the parking lot. It’s a steep way down, but the South Fortuna stairs provide lovely views.
Loop back down for a different perspective through a shady oak canyon.
North Fortuna – 5 miles / 1,140-foot elevation gain
Beginning at the Mission Dam pause before you begin the journey to learn some history of the region.
You may be surprised to see a lot of water in the desert if you are visiting in the right season.
The Oak Canyon trail passes by some colorful displays and over a bridge, relaxing for the time being.
Follow signs to the Fortuna Saddle trail pointing towards the summit, where the true grit begins.
Along a gravel fire road things get steep, gaining 500 feet in a half a mile, but the summit scenes are of course worth the effort.
Once again, shockingly, this place of epic beauty in the middle of the city was all mine.
Views here are utterly magnificent in every direction, from the city, to the sea, and the endless rolling hills.
A box filled with notebooks signed by other hikers is an interesting attribute to this summit, read some entries or leave your own mark.
Making a loop out of this trail is possible, by following the Perimeter trail which has some odd sights. Find a lone swivel trail nearly on top of the mountain, a wonderful spot to take a break.
Heading down this way is extremely steep and slippery, only recommended for those who are quick on their feet.
A bridge over a ravine is a good distraction, and signifies the end of the difficult section.
From here loop back to the Oak Canyon trail where it is smooth sailing from then on.
Bonus: Lake Murray – 6 miles / minimal elevation gain
If you’ve completed the challenge, or you’d like to do a hike that is more relaxing, try another fun trail within the park.
Mostly flat and paved, this is a very popular lakeside stroll, bike ride, or jog.
Birding here by the water is great, you’ll find a lot of waterfowl swimming about.
Likely there will be hawks and hummingbirds around this active environment as well.
A bunny nibbled trailside ready to dart, and many lizards scampered in a frenzy.
Strangely, the three mile path does not create a loop back to the parking lot – but ends at a chain link fence.
So to complete the trail, out and back is a decent amount of mileage – but you’ll find a conveniently placed restroom towards the end.