Mission Trails Regional Park (MTRP) is a 7200 acre recreation area in San Diego County. It’s amazing to think that it’s nearly 60 miles of trails are located just 8 miles away from downtown San Diego. There are five main peaks located within Mission Trails Regional Park, Cowles Mountain, Pyles Peak, Kwaay Paay Peak, South Fortuna, and North Fortuna. The vast majority of visitors to MTRP hike to the summit of Cowles Mountain and call it a day, having never taken the time to explore the other sections of the park. To help bring awareness to the expanse of Mission Trails Regional Park, and to distribute trail traffic, the 5 Peak Challenge was created in 2015. The challenge is for hikers and trail runners to visit all 5 peaks within MTRP using established park trails.
In April of 2017, I decided to take on the 5 Peak Challenge, and to complete it in one day! I heard a gentleman at the visitor center say that only 5% of 5 Peak Challenge finishers do it in one day. Now that I have completed the 5 Peak Challenge, I will include my strategy, photos, maps, and planning resources into this 5 Peak Challenge Guide.
Rules of Participation
- To complete the 5 Peak Challenge, use the MTRP trail map to hike on established trails to the five peaks. MTRP includes suggested routes using the color coded trails below. I will include my map, strategy, and logistics later in this post.
Trail Map With Recommended Routes from http://www.mtrp.org 
- Take a selfie or self portrait at the summit of each of the five peaks. Make sure to get the summit marker or post in each photo.
Cowles Mountain
Pyles Peak
Kwaay Paay Peak
South Fortuna Summit
North Fortuna Summit - Email the summit photos to 5-peakchallenge@mtrp.org at the completion of your challenge. Include your full name in the email, to be used on your certificate. After you’ve been notified, stop by the visitor center from 10AM-4PM to collect your certificate and pin.
*You can also stop by the visitor center on the same day as your challenge for a ‘walk-in’ submission if you’re from out of town like me.*
Completion Certificate
Resources, Maps, and Directions:
Being from out of town, I knew I would need to complete the 5 Peak Challenge in one day. To make this one day challenge as manageable as possible, I started looking at the map to find the shortest route using established park trails. I realized early on, that the best strategy would be to start early with Cowles and Pyles since they can be done together, and because Cowles is the most crowded. From Cowles and Pyles, I drove to the trailhead of Kwaay Paay. From Kwaay Paay, I drove to the East Fortuna Staging Area for South And North Fortuna. I could have avoided driving from trailhead to trailhead with a few miles of road hiking, but wanted to save time and mileage.
In the sections below, I will break down the three hikes I did to cover the five peaks in the 5 Peak Challenge. Here is an aggregate overview of the entire 5 Peak Challenge using my trail connections and strategy.
- I began the 5 Peak Challenge by hiking Cowles Mountain and Pyles Peak. To do this drive to 7027 Golfcrest Dr, San Diego, CA 92119. There is a small parking lot at the trailhead that fills up quickly, but residential street parking is also available.
- Download Cowles and Pyles GPX
- Download Kwaay Paay GPX
- Download South and North Gortuna GPX
- See my track on AllTrails
- Download PDF
- Total Distance: 15.77 miles
- Total Elevation Gain: 4249 ft
- Minimum Elevation: 305 ft
- Maximum Elevation: 1592 ft
- Time: It took me a little under 6 hours to hike all six peaks from start to finish. This is doable if you’re in peak fitness, otherwise budget much more time, or plan on completing the challenge over multiple days.
- Difficulty: Moderate (3 out of 5)
- Dog Friendly: Yes, on leash
- Permit Required: No
- Season: Year round
- Trail Condition: The trail is somewhat steep in places, but well maintained, well marked, and easy to follow.
- Cell Phone Reception: Very good
- Make sure to hike with the right gear. See my current hiking gear list.
The 5 Peak Challenge Of Mission Trails Regional Park
Cowles Mountain and Pyles Peak – Peaks 1 and 2
At 1,592ft, Cowles Mountain is the highest peak in the city of San Diego. The hike to the summit of Cowles is possibly the most popular hiking route in all of San Diego County, which makes an early start a requirement for the 5 Peak Challenge. Hiking to the nearby Pyles Peak is far less popular, and the perfect addition to a hike up Cowles.
Directions And GPS Tracks:
- To hike to the summits of Cowles Mountain and Pyles Peak, drive to 7027 Golfcrest Dr, San Diego, CA 92119. There is a small parking lot at the trailhead that fills up quickly, but residential street parking is also available.
- Download GPX
- See my track on Strava
Key Points:
- Distance: 6 miles
- Elevation Gain: 1854 ft
- Minimum Elevation: 668 ft
- Maximum Elevation: 1592 ft
- Time: 2-4 hours
- Difficulty: Moderate
- Dog Friendly: Yes, on leash
- Permit Required: No
- Parking: Parking lot at trailhead and street parking for overflow
- Season: Year Round
- Trail Condition: The trail is somewhat steep, well maintained, well marked, and easy to follow
- Cell Phone Reception: Very good
Make sure to hike with the right gear. See my current hiking gear list.
Hike Map And Elevation Profile:
Hike Description:
0.0 Miles- As I mentioned in the intro, this is a very popular hike that can get very crowded. Make sure to arrive early. I started this hike at 6:30 AM to make sure I’d have enough time and space to enjoy the trail. There are restrooms located at the trailhead next to the signage for “Cowles Mountain Staging Area”.
The first quarter mile of hiking is very gradual, but the incline quickly increases. Take time to enjoy the blooming wildflowers (seasonal), and don’t forget to look back at the city views that will increase with every step upward.
The trail for Cowles Mountain is in great condition, but the rainy season can leave sections rutted, and erosion can expose stones that will leave unprotected feet tender. Make sure to wear good trail shoes with grip and protection for this hike. You can check out my guide to finding the perfect trail shoe if you’re in need of a new pair.
0.5 Miles- You’ll have a view with two peaks up ahead. The trails wraps around the first hill to the right and then Cowles will be the higher mountain to the left.
0.9 Miles- You’ll see the junction for the Barker Damn Trail. This is another trailhead start option if you’d prefer to avoid the high traffic found at the Cowles Mountain Staging Area. Keep left at the junction to continue on to Cowles Mountain.
Just after passing the Barker Dam trail junction, you’ll scale a series of switchbacks that will take you to the summit of Cowles Mountain.
1.5 Miles- At 1.5 miles you’ll be standing at the summit of Cowles Mountain. Take a look around, enjoy the views, and then make your way to the north end of the summit towards the antennas.
When you see the antennas and a rock outcrop take a left (west) to pick up the Pyles Peak Trail. You’ll see a small brown sign close to the ground that reads Pyles Peak Trail.
After hiking uphill to the summit of Cowles Mountain, you’ll have two descents and two ascents before reaching the summit of Pyles Peak. You’ll be able to catch glimpses of Pyles Peak and Kwaay Paay Peak up ahead.
2.3 Miles- You’ll see a sign for “View Point”. This is a short side trail that takes hikers to a viewpoint between Pyles and Cowles. Continue on towards Pyles Peak by continuing straight ahead.
2.6 Miles- You’ll see the final trail sign for Pyles Peak with a view of the summit above.
3.0 Miles- You’re standing on the 1,379ft summit of Pyles Peak. From this point, you can turn around and return to the trailhead on the same path that you arrived with.
Kwaay Paay Peak – Peak 3
Kwaay Paay Peak is probably the least renowned of the five peaks in Mission Trails Regional Park. At only 2.4 miles roundtrip, it’s a hike that on paper seems rather unremarkable. The experience in person is quite different though, as the 1.2 miles to the peak gains almost 900 feet, and offers amazing views of the nearby South and North Fortuna summits.
Directions And GPS Tracks:
- To hike to Kwaay Paay Peak you’ll head to the Father Junipero Serra Trail, drive to 1 Father Junipero Serra Trail, San Diego, CA 92119. You can also start this hike at the Old Mission Dam, which is about a quarter mile west of the main Kwaay Paay Peak trailhead. There is parking available along the street on Junipero Serra Trail, and in a few lots as well.
- Download GPX
- See my track on Strava
Key Points:
- Distance: 2.4
- Elevation Gain: 867 ft
- Minimum Elevation: 305 ft
- Maximum Elevation: 1194 ft
- Time: 1 hours
- Difficulty: Moderate
- Dog Friendly: Yes, on leash
- Permit Required: No
- Parking: Parking lot at trailhead and street parking
- Season: Year Round
- Trail Condition: The trail is steep, well maintained, well marked, and easy to follow
- Cell Phone Reception: Very good
Make sure to hike with the right gear. See my current hiking gear list.
Hike Map And Elevation Profile:
Hike Description:
0.0 Miles- Starting on the trailhead leaving from Junipero Serra Trail, walk along the dirt path heading southwest. Just 0.1 miles into the hike, the trail forks, giving hikers two options towards the summit of Kwaay Paay. I suggest keeping right at the junction for a more direct route.
0.25 Miles- You’ll reach the top of your first climb, and get a taste of the views that await you at the summit of Kwaay Paay. After a very brief downhill reprieve, your climbing will begin again in earnest.
0.8 Miles- You reach the steepest part of this hike. There are a few sections that are loose with gravel filled ruts. Make sure to be mindful of your footing here, especially on your way back down.
1.2 Miles- Kwaay Paay Peak! Take in the view of Cowles Mountain and Pyles Peak to the southeast, and views of North and South Fortuna to the northwest.
South Fortuna and North Fortuna – Peaks 4 and 5
Having hiked to the summits of all five peaks within Mission Trails Regional Parks, the hike to South and North Fortuna from the Fortuna Staging Area was easily my favorite. This hike offers solitude, a trail that parallels running water (seasonal), and the chance to bag two peaks in quick succession for a grand finale to the 5 Peak Challenge!
Directions And GPS Tracks:
- To hike South Fortuna and North Fortuna Mountains, you’ll head to the East Fortuna Equestrian Staging Area. Drive to Equestrian Cir, Santee, CA 92071. There is parking in a dirt lot right near the trailhead of the Spring Canyon Trail.
- Download GPX
- See my track on Strava
- To begin this hike, you can start out on the Spring Canyon Trail or the North Perimeter Trail. You’ll see both heading west in the aerial image below. For this hike writeup, I started with the Spring Canyon Trail and returned via the North Perimeter Trail.
Key Points:
- Distance: 7.1 miles
- Elevation Gain: 1354 ft
- Minimum Elevation: 305 ft
- Maximum Elevation: 1291 ft
- Time: 3-4 hours
- Difficulty: Moderate
- Dog Friendly: Yes, on leash
- Permit Required: No
- Parking: Parking lot at trailhead
- Season: Year Round
- Trail Condition: The is very steep in places, but well maintained, well marked, and easy to follow. There is a section of this hike that can be along water depending on the season.
- Cell Phone Reception: Very good
Hike Map And Elevation Profile:
Hike Description:
0.0 Miles- Start out on the Spring Canyon Trail located at the north end of the East Fortuna Staging Area.
There are two spots in the early stages of this trail that can be covered with water in the rainy season. There are rocks to help hikers get from one side to the other.
0.4 Miles- As the Spring Canyon Trail heads southeast, it intersects with the Grasslands Loop(Crossing) Trail and the North Perimeter Loop Trail. Both of these trails will take you east and eventually where you need to go. For this hike, I stayed on the Grasslands Loop Trail.
0.8 Miles- The Grasslands Loop Trail will run along a wooden fence. Follow the trail along the fence, due south.
1.0 Miles- Leave the Grasslands Loop behind for the Oak Canyon Trail. This is an easy junction to miss, so keep your eyes open!
Oak Canyon Trail runs along a shaded creek for 0.2 miles before venturing out into a little more exposure.
1.3 Miles- The creek takes a turn as the trail heads east, and swells with more water than before. You’ll get to cross over a few bridges here. Make sure to take a little extra caution with your footwork on this stretch of the hike as the rocky trail can be loose in areas.
1.6 Miles- The Oak Canyon Trail intersects the Fortuna Saddle Trail. Head east on the Fortuna Saddle Trail.
Once you’re on the Fortuna Saddle Trail, things start get steep. You’ll gain 500ft of elevation in the next 0.6 miles. I saw one lady fall heading downhill on this section, so make sure to keep your feet firmly planted beneath you.
2.2 Miles- Once you reach the Fortuna Saddle, you can decide if you want to bag South Fortuna or North Fortuna first. I like to finish with the highest peak last, so I took a left at the saddle to summit South Fortuna first.
2.8 Miles- The 1094ft summit of South Fortuna was empty on this day, as it is not a popular destination in the Mission Trails Regional Park. All the more reason to enjoy this one and all the solitude it provides.
Once you’ve spent enough time at the summit, make your way back down to the saddle to summit North Fortuna.
3.4 Miles- Once you’ve made it back to the saddle, head up the trail to North Fortuna. I came upon a rattle snake on this outing. Make sure to keep your eyes open for rattlers all throughout Mission Trail Regional Park.
4.0 Miles- There is a false summit just before reaching the actual summit of North Fortuna. You’ll know you’ve reached the top at 1291ft when you see the summit register and summit post sign.
Once you’ve enjoyed the views and taken some time to rest your legs, you can return the way your arrived via the Fortuna Saddle Trail.
Bravo, Drew! A job well done on the 5 Peak Challenge.
Thanks, Mike!
Well done, Drew! Looks like a great set it trails, and your photography is outstanding as usual. Your level of fitness always amazes me. I wish I could hike that fast!!!
Thanks! It’s a great little network of trails.
hi me and my classmates went on this hike on a fieldtrip to pyels peak and it was really fun! Honestly I think it’s the best exersice.
Awesome! I hope you enjoyed it!
So helpful! We’re tackling it this weekend and I’m so happy I found this!
Thanks, Charity! I’m glad you found it useful. Good luck this weekend!
Sounds like you’re ready to do the 6 Peak Challenge! Some of us have added El Cajon Peak to the mix for a one day epic hike. If you do El Cajon Peak last (like most do), be sure and park outside the designated parking area because the gate is locked at 6pm (varies by season). ECP will add another 4-6 hours to your day hike and give your legs a real burn after the warmup on the other five peaks. Take lots of water because there is no shade on ECP. Enjoy!
I didn’t know there was a 6 peak challenge! Thanks for the tip on El Cajon Peak. That looks like it would be the ultimate way to cap off the MTRP challenge.
Um, El Cajon Peak adds 12 miles and almost 4000′ elevation to this. That would end up being a 27 mile day with about 8000′ elevation. Whoa!
That’s a monster day. I’m going to try it when the weather gets a little cooler here in SoCal. I’m hoping for a 60 degree day soon.
Nice job, thanks for all the great advice and tips my wife and I will try it next mth
Thanks for reading. I hope you have fun, it’s a great challenge!
Thank you for your information, a group of hopefully 20 or more will be doing this 5 Peak Challenge on January 27, 2018. Can’t wait!!!!
Wow, that’s a big group!
I did this today…wow that was a lot of climbing! I went a different way to the fortunas, no bridge, and there was no water at this time. I did Mt. Whitney 5 weeks ago but haven’t conditioned since, and it took me 7 hours. This was a long, challenging hike!
Congrats, Dana! The 5 Peak Challenge is a great accomplishment.
Hey bud! I’m an ultra runner and looking to do this run next week. I’m a little confused on the route to take. Can you get in touch with me? I’m on Facebook as Tonya keyes-christianson
You can email me at trailtopeak@gmail.com
Thanks for the great post about the Five Peaks. My friend and I did the challenge over Thanksgiving weekend in 2015. We’re going to do them all on Feb 25th but we’re going to take 90 minute rests after the first two and Kwaay.
Hoping to get them all finished between sunrise and sunset
Sounds like a good plan. Hitting all 5 peaks in one day is a fun challenge. Have fun!
Good luck and enjoy!!
Thanks for the info. Myself and 2 of my girlfriends tackled all 5 peaks yesterday! It was a long, fun day!
Congrats on hitting all 5 peaks in one day!
Thanks for posting this great post! I was in SD today and only had today to do the challenge and I mostly followed your instructions which were very well written! The pictures helped too. This was an excellent guide for me today. I only got a little off track going up and back from the Fortunas. But, I completed the challenge. Thank you!!! -Helen
You’re welcome, Helen. Congrats on completing the challenge!
Made it through in two days. (started late on day one) Cowles, Pyles and Kwaay Paay last weekend and Fortuna today. Fortuna (north and south) could now be a favorite hike for me! Great directions and thanks for making us aware of this great challenge!
Congrats!
Awesome job and great pictures The park is only that green for a couple of months every year (This year not at all.) You missed the infamous South Fortuna Stairs using your route but any route including them would have been longer.
Thanks! I’ll have to try that route next time!
Your blog post is going to be like my bible. Haha. Doing this in one day to raise money for CAF. Thank you! Saved me a lot of logistical issues!
Awesome!
Can you do the challenge in one day if you go from peak to peak without descend from each summit? I am doing it with my Meetup group on Feb 2nd and I can’t find much info by way of mileage if we just keep trekking towards the next trail. Thanks for any input you have.
Can’t really be done. You can do the two Fortunas without descending, but you have to cross a road from there to get to Kwaay Paay, and you have to drive to get to the start of the other two.
There are not trails connecting all of the peaks together, per se. Plus, two peaks are on one side of a highway and three on the other. I would suggest parking at Cowles and doing Cowles and Pyles (there is a trail connecting those two together), them drive to and park at the Old Mission Dam parking lot at Mission Trails Regional Park (it is a small parking lot, but there is plenty of parking on the road). Next do Kwaay Paay, then you’ll come back past your car (restock food & water, if needed), and finish with South and North Fortuna (they are connected). There are other trails to the top of each peak, but they would more driving to each trailhead (I’ve done them all). It is very doable in a day and I hope you have a great hike.
That is correct. There is no trail that links all 5 peaks, and a car free outing would require quite a bit of road walking/running. The next time I do this I’m going to park at the Old Mission Dam to do Kwaay Paay and then head over on foot to summit the Fortunas.
I attempted North Fortuna and after over 3 miles reached a peak then the trail continued to a locked gate right next to the freeway. We didn’t go down this trail . Where is the peak? What did we miss? Thanks!
Hard to answer given the information provided. Did you track your route on your phone? If not, I would recommend using an app like Strava or AllTrails to track your hike and see where you are on the map in real time. You can also use my GPX track to compare your route.
Thanks so much for posting this. I followed your route mostly, and completed it today; albeit it took me longer. (I am 65….so I get some slack, I hope! The first four felt pretty good; i.e.. cardiac arrest didn’t feel imminent. The fifth…let’s just say I was giving thanks there wasn’t a sixth.) It is wonderful to have your fantastic pictures as a memory since they are excellent, and I am also slacking in that department. Really and truly thank you!
Great to hear and congrats!
Great blog and really helpful, thanks! Did Cowles and Pyles yesterday.
Question for you: what is the shortest distance, doing the Fortunas separately using the MTRP suggested routes, or all at once through the saddle?
I am wanting to attempt North/South Fortuna this weekend. You think it would be a trail ok for a 7 month preggo? 😬
Hi Sharlene. I think it depends on the pregnant woman. Any route up to the Fortunas is pretty steep. Going up to the saddle from the Old Dam on Junipero Serra Blvd requires a bit of rock hopping and scrambling through Oak Canyon, and then a long slog up a very steep access road, and then once you get to the saddle, it’s still a pretty steep climb up to either summit. Going from the other side, up the South Fortuna Stairs, is even steeper. The trails are all well-trodden and maintained, but they’re also rocky and rugged in spots, due to erosion and can be slippery with loose sand and gravel, particularly if you’re not wearing good footwear. I think if you’re in shape it shouldn’t be a problem; just exercise care.
Depends on your fitness level. As Matt correctly stated, both routes are steep. I would recommend trekking poles just to make sure you don’t slip somewhere. Sometimes the loose dirt and small rocks act like ball bearings, particularly on the road to the saddle out of Oak Canyon.
Thank you Drew for a wonderful report. I wanted to quickly share my experience. Visited from Phoenix last week and completed the challenge. After Cowles/Pyles, I drove and parked at Old Mission Dam to complete other 3 peaks. (wanted to limit driving). Loved being able to refuel at car after Cowles/Pyles and again after Kwaay. Coming down the slippery Fortuna Saddle trail was the most difficult (i.e. knee busting) section for me. I started at sunrise to limit the heat. My stats: 13.8 miles, 3,934 ft gain, 4 hr 16 mins hiking time. Plus 8 mins of driving time and 10 mins of refueling time. I hiked quick and ran several flat/down sections. Thanks again.