On Saturday, November 7, Mission Trails Regional Park announced the 5-Peak Challenge to bring attention to the park’s 60 miles of mixed-use trails that lead to 5 of the highest peaks in the city of San Diego.
Mission Trails is home to some of my favorite local hikes, so there was no question whether or not I was going to take on the challenge, it was just a matter of timing.
Read: My trail reports for each of these five peaks.
I reached out to my friend Alan (Instagram @max2945) and we decided that at 7am on Thursday we would set out to conquer all five peaks in one day.
We met up at the park’s Visitors Center, where we laced up our shoes, filled up our hydration packs and made our way to the Visitors Center Loop Trail to start our adventure.
Our goal was simple, bag all five peaks in the most efficient way possible, and working out the logistics for our 15.7 mile hike was pretty straightforward.
Here’s the route we picked (distances are approximate):
Visitors Center to South Fortuna Peak (2.75 mi)

- Visitors Center Loop Trail to San Diego River Crossing Trail
- San Diego River Crossing Trail to Suycott Valley Trail
- Suycott Valley Trail to South Fortuna Trail
- Bag South Fortuna Peak (1094 ft.)
South Fortuna Peak to North Fortuna Peak (1 mi)

- South Fortuna Trail to Fortuna Saddle Trail
- Cross Fortuna Saddle trail to North Fortuna Trail
- Bag North Fortuna Peak (1291 ft.)
North Fortuna Peak to Kwaay Paay Peak (3 mi)

- North Fortuna Trail to Fortuna Saddle Trail
- Fortuna Saddle Trail to Oak Canyon Trail
- Cross Old Mission Dam and hike to the parking lot
- Parking lot to Kwaay Paay Trail
- Bag Kwaay Paay Peak (1194 ft.)
Kwaay Paay Peak to Visitors Center (3 mi)
- Kwaay Paay Peak to Father Juniper Serra Trail
- Father Juniper Serra Trail to Visitors Center
We took a brief break at the Visitors Center, refueled and hydrated, then hopped in a car and drove the short 2.25 miles over to the Cowles Mountain Trailhead. From the trailhead, we set out to bag our last two peaks.
Trailhead to Cowles Mountain Peak (1.5 mi)

- Cowles Mountain Trailhead to Cowles Mountain Trail
- Bag Cowles Mountain Peak (1592 ft.)
Cowles Mountain Peak to Pyles Peak and back to the trailhead (4.5 mi)

- Cowles Mountain Trail to Pyles Peak Trail
- Bag Pyles Peak (1379 ft.)
- Pyles Peak Trail to Cowles Mountain Trail
- Cowles Mountain Trail to the trailhead
From the trailhead, we once again hopped in our car and headed back to the Visitors Center where we picked up our hard-earned 5-Peak Challenge Finisher Pins.
On to the next adventure!
Have you taken on the 5-Peak Challenge? Tell me about it in the comments below.
My Run Keeper Stats
- Miles: 15.67
- Hiking time: 6:00:12
- Calories burned: 2268
- Elevation gain: 4378′
Maps & Location
- 5-Peak Challenge Trail Map (provided by MTRP.org)
- Detailed trail map (provided by MTRP.org)
- Mission Trails Visitors Center (via Google Maps)
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