The Mission Trails 5-Peak Challenge: all five summits, and how to do them in one day
Summit Cowles, Pyles, Kwaay Paay, North Fortuna and South Fortuna, all inside Mission Trails. Done in one day it's roughly 13 to 15 miles with about 4,000 feet of climbing; split up, each is a half-day hike.
- Peaks
- 5
- Highest
- 1,592 ft
- One-day total
- ~13-15 mi
- Cost
- Free
All in Mission Trails Regional Park
Cowles Mountain
About 4,000 ft of gain
No permit needed
The short version
- The five peaks are Cowles Mountain (1,592 ft), Pyles Peak (1,379 ft), North Fortuna (1,291 ft), Kwaay Paay (1,194 ft) and South Fortuna (1,094 ft), per the San Diego Reader.
- You can do them in any order, over any period; the classic proof is a photo with each summit sign.
- In one day, hikers report roughly 13 to 15 miles and about 3,400 to 4,300 feet of gain, depending on the route.
- Park at Barker Way for Cowles and Pyles, and at the Old Mission Dam lot for Kwaay Paay and the Fortunas.
- The park ran an official pin-and-certificate program from 2015; a 2024 report says it has ended, so check with the Visitor Center at (619) 668-3281.
Mission Trails Regional Park, about 8 miles from downtown, holds five named summits. Bagging all five is San Diego's favorite local hiking challenge: a weekend project for some, a single brutal day for others. Here's the list, the logistics, and the honest status of the pin.
Peaks
Parking
Pins are approximate. Sources: San Diego Reader, She Explores the USA and OpenStreetMap, checked October 6, 2026.
See these on the full San Diego mapThe peaks at a glance
| Peak | Elevation | Usual start |
|---|---|---|
| Cowles Mountain | 1,592 ft | Barker Way or Golfcrest Dr |
| Pyles Peak | 1,379 ft | Barker Way, via Cowles |
| North Fortuna | 1,291 ft | Old Mission Dam lot |
| Kwaay Paay | 1,194 ft | Old Mission Dam lot |
| South Fortuna | 1,094 ft | Old Mission Dam lot |
Elevations from the San Diego Reader, December 2019.
A one-day plan
- 01
Start east, at first light
From Barker Way, climb Cowles, then follow the ridge north to Pyles and back. One hiker logged a little under 6 miles and nearly 2,000 feet of gain for this pair.
- 02
Drive to Old Mission Dam
The lot on Father Junipero Serra Trail is the base for the other three, and you can see the 200-year-old Old Mission Dam on the way.
- 03
Kwaay Paay, then the Fortunas
Kwaay Paay is short but steep. The Fortunas join by a saddle; the same hiker logged about 7 miles and 1,400 feet for North and South Fortuna together.
- 04
Take your proof
Snap a photo with each summit sign. It's how the official program verified finishers, and it's the bragging rights either way.
- Water: carry plenty; there's little shade on any of the five.
- Season: fall through spring. Summer afternoons in the park get hot.
- Free: no permit or parking fee at these trailheads.
SOURCES
Everything above traces back to one of these. Follow them — if one has changed and we haven't, that's our mistake, not yours.
San Diego Reader · December 4, 2019
Peak elevations, photo proof, certificate and pin process
San Diego Reader · January 17, 2023
One-day route segments, distance and gain
She Explores the USA · May 2024
Official program ended around 2020; parking areas; one-day totals