5 Peak Challenge Mission Trails Overview

My wife and I have been slowly preparing to make an attempt at Cactus to Clouds this year and have been planning out a series of longer day hikes in preparation. This past weekend we embarked on the San Diego 5 Peak Challenge in Mission Trails Regional Park. The 5 Peaks challenge can be hiked in three main configurations:

Hike all 5 peaks doing one peak a day
Hike all 5 peaks and drive between trailheads
Hike all 5 peaks and walk between each trailhead

For our 5 Peak Challenge attempt we woke up a little late and decided to go with option two. My wife planned out a great route in Caltopo and broke it down into two parts.

Part 1: Kwaay Paay, North Fortuna, South Fortuna (9.41 miles / 2,474 ft elevation gain)
Part 2: Cowles and Pyles Peak (6.06 miles / 1,795 ft elevation gain)

Total mileage for us was 15.47 miles with 4,269 feet of elevation gain hitting each peak in one day according to my Garmin Fenix Fenix 7 (Amazon Affiliate).

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San Diego 5 Peak Challenge Maps

For part one (Morning hikes) of our San Diego 5 Peaks Challenge we hiked Kwaay Paay, North Fortuna, and South Fortuna. Our part one map can be viewed and downloaded on Caltopo here.

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For Part two (Afternoon hikes) of our San Diego 5 Peak Challenge we hiked Cowles and Pyles Peak. Our part two map can be viewed and downloaded on Caltopo here.

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5 Peak Challenge Gear List

Since my wife and I are training for Cactus to Clouds, my pack was definitely on the heavier side of things. Additionally I love photography so my starting pack weight for this trip was 21.17 pounds.

Pack Weight breakdown:

Base Weight 12.4 lbs
Consumable Weight: 8.77 lbs
Worn Weight: 4.85 lbs

My consumable weight was pretty much all water. I took 4 Liters and drank ever last drop. I ended up drinking more then 4 Liters total though because we stopped for lunch where I drank another glass and a tall soda. My wife carried all the snacks that we ate on the trail.

You can check out my full pack out here.

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Peak 1: Kwaay Paay

My wife and I got to the trailhead around 9 am for a bit of a late start. Our plan was to start on Kwaay Paay which is short and steep, then cross the street and Hike North and South Fortuna. If you hike North Fortuna first you get a little bit of a flat section in between finishing Kwaay Paay and starting North and South Fortuna.

Parking for part one was pretty easy. There are multiple sections you can start at for Kwaay Paay, and we decided to park in between our start and end section of Kwaay Paay. This allowed us to start up the western trail and come down the eastern trail and then directly cross the street to North and South Fortuna.

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After parking along Father Junipero Serra Trail we walked for a short bit along the road before hitting the Kwaay Paay Trailhead.

For longer hikes like this, I like to upload my GPS route to my Garmin Fenix 7 (Amazon Affiliate), so I can watch the elevation tick away as we tackle each peak. Before stepping off onto Kwaay Paay I took a quick peek down at my watch to get a quick glimpse at what the morning had in store with us:

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Kwaay Paay is the steepest of the climbs, so we decided to tackle it first. With Kwaay Paay being our first climb of the day, the San Diego haze was still hanging around, which helped keep us cool at the start. I was optimistic that it would last most of the day but I was wrong, it pretty much all burned off before we got to the top of Kwaay Paay.

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Hiking up Kwaay Paay our legs were nice and fresh with it being our 1st of 5 peaks. I felt like we were moving at a good pace as we zoomed up the trail.

Our momentum was quickly squashed though as I had some camera issues on the trail. My shutter on my Sony Camera got stuck in the closed position. After some tinkering I was able to snap back up. After a couple more tests it kept getting stuck closed after each shot which was super unfortunate. Luckily the Sony A9 has a silent shutter mode which doesn't use the shutter, so I could limp along with my photography.

Kwaay Paay is known for its steep climb and many stairs on the way to the peak. But if you just put one step in front of another, Kwaay Paay flies by and you are suddenly at the top!

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It took us just under 40 minutes to get to the Top of Kwaay Paay and just like that in under an hour our first of 5 peaks was in the bag! At the top we sat down to enjoy the view for a minute and drink some water, as the haze was burning off and the sun was getting stronger. Usually when hiking we spend some more time at the peak, but we had to watch our time to make sure we could hit all 5 peaks today. After a quick sip of water it was right back down what we just climbed up.

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Peak 2: North Fortuna

With Kwaay Paay bagged, we had 4 more peaks to go and we were feeling pretty good at this point. I quickly check my Garmin Fenix 7 (Amazon Affiliate) to check on our progress, and to mentally prepare for the next climb up North Fortuna.

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North Fortuna has a bit more of a build up before the big steep sections. The route we chose for North Fortuna has some pretty steep rolling hills before the main climb to the top, which is pretty punishing on your quads. But before then the hike starts out beautiful and peaceful.

As you enter the trail after crossing the street from Kwaay Paay it's nice and shaded with a pretty bridge over the water. It's a great welcome into the grassland area where shade will become very sparse for the rest of the hike.

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As you exit the short bit of shaded trail you enter the grasslands and get to enjoy some nice wide open trail and views. From here you will slowly be making your way towards the 52 Highway. Enjoy this section as much as possible, it's the calm before the storm for your quads.

We continued following signs for the North Fortuna Perimeter Trail. The signs remind you that you are on a "difficult" trail. The difficulty will begin once you get close to the 52 highway bridge that the trail will parallel.

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This section of trail is a series of steep fire roads that are absolutely quad busters. The fire roads aren't exactly smooth either so there are lots of large loose rocks that just add to the fun as you are climbing up them.

At this point in our hike it was starting to get pretty warm as well. All the morning haze had pretty much burned off at this point.

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This section of trail was probably the hardest part of the day. The trail was steep, it was hot and they were rolling climbs... Since they were rolling climbs, you would expend your energy climbing the steep fire road then you would get to the top of that section and it would go back down a bit before climbing the next steep section. Having those small down hills before the next steep climb is always fun mentally. Also don't get too excited when you get to the top of one because there are a couple false peaks..

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Eventually the trail leads you right next to the highway. The first time I came on this trail when we were scouting out the 5 Peak Challenge I thought we hit a dead end because you see a fence down by the highway and the trail seems to end there.

Once you get down to the fence there are some stairs you follow, as the trail hugs the fence for the final push up to North Fortuna.

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In the area by the fence there is a little shade and we stopped here for another break to sip some water in the light shade cover before the final push up towards the peak. After this brief stop in the shade, the trail takes a little bit of a more relaxed climb which is a nice break after those steep rolling hills. This nears the end of the North Fortuna Perimeter trail and the signs will begin to change to North Fortuna Trail as you make your way closer to the peak.

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As we got closer to the summit, I was getting excited knowing that the two hardest climbs of the day would be behind us at that point. I seemed to get a second wind as we pushed to the top of North Fortuna.

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Once again unlike most peaks we bag in San Diego, this was a quick stop. After bagging Kwaay Paay and North Fortuna, we still had 3 more peaks to go before calling this challenge complete! At this point I did need to transfer water from my extra reservoir in my pack to my main water bottle and top it off. We also stopped long enough to split a power bar for a quick snack.

Hindsight 20-20, I probably should have eaten a full power bar at this point. I figured it was mostly down hill at this point and I didn't want to spoil lunch... but we had burned a lot of calories at this point. On a hot day, drink lots of fluids and make sure you keep eating.

Peak 3: South Fortuna

Approaching South Fortuna from North Fortuna makes it the easiest peak of the day. There is a nice saddle that connects the two peaks. It's a nice little downhill and then just a small climb up to South Fortuna.

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As we descended from North Fortuna across the saddle to South Fortuna it was nice to be going down hill for a bit. Once the trail leveled out and started to climb towards the peak of South Fortuna, it was a steady climb and felt like nothing when compared to what we had climbed already today.

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South Fortuna was another quick summit, just a quick swig of water, a couple pictures and a handful of beef jerky to munch on the way down.

From the South Fortuna Summit we turned around descending what we just climbed along the saddle between North and South Fortuna. At the low point of the saddle we turned off the saddle trail and headed back towards the grasslands loops.

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This down hill was pretty steep and I took out my hiking pole to help relieve some pressure on my IT band, which I have had problems with in the past. My IT band was feeling pretty good after bagging the 3rd peak, and I wanted to make sure it lasted for the final two peaks we had coming up after lunch.

As the steep trail levels out you hit the most beautiful section of trail as you follow a little creek the rest of the way down.

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The last section back through the grasslands and back to where our car was parked was fairly flat but felt long. I was starting to drag a little at this point and feeling pretty tired. I think if I ate some more calories on the trail I would have maybe been feeling a little better here. I was ready to get in the car and grab a delicious burrito before we hit the last two peaks. I needed to refuel for part 2 of the 5 Peak Challenge in one day.

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Lunch

After arriving at our car we had officially finished Part 1 of the 5 Peak Challenge in one day. Part 2 the final 2 peaks would be after a quick lunch to refuel our bodies.

There was a nice taco place called El Rancho on the way to the next trail head so we drove a few miles down the road and stopped for lunch.

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At lunch I killed half a burrito that also had large chunks of bacon in it! It was delicious and exactly what my body needed to feel human again. I destroyed the cold water and chips that our waitress brought us and also a large Dr Pepper.

I was refueled and ready to go for the final two peaks of the 5 Peak Challenge!

Peak 4: Cowles Mountain

Cowles and Pyles Part 2 of the 5 Peak Challenge, are similar to North in South Fortuna. You just have to climb one Peak then kind of scurry on over to the second Peak. We decided to Hike up Cowles from Barker Way Trailhead.

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If you look back at our Caltopo map from earlier in the article there are a number of different paths up Cowles Mountain. It starts on a wide service road but we turned off the main services road to go up the switchbacks.

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The switchbacks were amazing! I felt like we were gaining elevation fast but my quads still were feeling fresh! I didn't realize it until we hit these switchbacks that most of the day none of the trails had switchbacks.

After the first set of switchbacks we chose to join up with the service road... looking back I Probably would have stayed off the service road and gone towards the rest of the switchbacks on the route to Cowles Mountain summit.

You can see the red line below is our route, and you can see the switchbacks to the west that we did not take to the top.

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I don't know if it was because it was towards the end of a long day, the heat or a combination of both, but that service road just wasn't my favorite part at all. As we came out of the smaller trail back onto the service road we turned left and we could see the Cowles Mountain Summit was right there, it felt like we could touch it.

Despite feeling so close, the service road is steep and I was feeling it in the heat.

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Once we got to the top of Cowles I was ready to sit down and sip some water. We were at 4 of 5 peaks, with one more to go! This one more felt a little odd to think about because we would have to come back through the top of Cowles Mountain to get back to our car... so really had 1.5 peaks to climb? So Maybe the 5.5 peak challenge for us?

At the top of Cowles we quickly took in the great views of San Diego, and I especially enjoyed the View of Lake Murray. My wife always says that Lake Murray looks a little bit like a dinosaur foot. You could definitely see that from the top of Cowles.

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The hike from Cowles to Pyles is almost like going across to saddles. There is a dip down from Cowles and a small uphill climb to an unnamed peak that my map shows as "Peak 1380" then a slight downhill from there before climbing up to bag Pyles Peak.

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As we slowly meandered down towards the final uphill before Pyles Peak, the sun was getting lower in the sky. Summer days are long, and we still had plenty of daylight left, but I did have a head lamp packed just in case.

The sun hanging lower in the sky meant the temperatures were starting to cool off a bit, which made the final trek up towards Pyles actually quite pleasant. As we approached Pyles the shrubbery changed along with the lighting which created a magical looking glowing grass in the sunlight which seemed to be our welcome mat to the final peak in the 5 Peak Challenge!

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The final quarter mile to Pyles flew by and seemed much easier then Cowles. As we made it to the top of Pyles Peak we finally took a longer break to enjoy the view and relax a bit before hiking back down. There were a few other hikers at the top when we got there, and we hung around until they all left and we had it all to ourselves. It was nice to not be rushed to get to the next peak and just enjoy the view and our accomplishment together.

After some water, snacks and selfies it was eventually time to turn around and head back up to Cowles then back to our car and head home. The hike back seemed easy, we weren't chasing peaks anymore just a warm shower and a very large dinner!

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5 Peak Challenge Strava Stats

Since my wife and I were using this as a training hike for Cactus to Clouds, I really enjoyed looking at the Strava data for this hike and thought it may be interesting to others to see our trail stats if planning to tackle the 5 Peak Challenge in one day.

5 Peak Challenge Part 1 Stats:

Distance: 9.41 Miles
Total Time: 4:32:23
Moving Time: 3:50:40
Pace: 24:30 /mi
Elevation: 2,474 ft
Calories: 1,754

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5 Peak Challenge Part 2 Stats:

Distance: 6.06 mi
Total Time: 3:05:33
Moving Time: 2:34:17
Pace: 25:27 /mi
Elevation: 1,795 ft
Calories: 1,239

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