Why I Ran the Mission Trails Regional Park 5-Peak Challenge

Started in 2015, The Mission Trails Regional Park 5-Peak Challenge rewards those who hike to the summit of five nearby peaks in San Diego. Mesa Rim Regional Director of Operations, Keegan Dimmick, decided to run the near 16-mile coursein one day.

By Keegan Dimmick


Why do anything?

Here are a few of the more common comments I hear when people find out I enjoy running.

Running sucks…

Running is hard…

Don’t your knees hurt?

Doesn’t that take a long time?

Have you read Born to Run?

I have no idea why anyone would want to run, ever. There have been a few times in my life where I thought I knew why I liked to run. Then another year would pass, I would sign up for a race, and my motives would be completely different.

When I ran my first 50k I was convinced that I wanted to do it because it sounded really fun! I showed up to that race and ran my heart out. I finished in the top 10, and although I suffered, I had a great time. Since that race I have run marathons and 50k’s to be with friends, to accept friendly challenges, and prove to myself that I’m not a has-been. Then, something clicked for me this year and I started running just for an opportunity to be in the mountains; to be in nature.

When I envision myself, the person I see lives a life touched by the forests, rocks, and secrets hidden within the mountains. I feel a strong sense of pride in myself when I’m look back on the battles that have been fought with steep trails, early mornings, unexpected body functions, and the elements.

The Mission Trails Regional Park 5-Peak Challenge was one of those battles and as soon as I learned about it I knew I had to give it a shot.

The official objective is to summit the five peaks: Cowles Mountain, Pyles Peak, Kwaay Paay, South Fortuna, and North Fortuna. The official challenge has no timeline, and the only requirement is once you summit the peak, you take a picture with the summit sign. I was smack in the middle of a training cycle to race the Noble Canyon 50k for the third time. I knew I needed some longer distance days and the 5 Peaks Challenge was a great opportunity to train hard, with the convenience of being close to home, so I decided to go for it and complete the challenge in one day.



I like to get prepared for longer runs the night before. I got my hydration pack filled up, snacks packed, and running gear out (see gear list at the end). I also made a trail map for myself because there were a few trails I had not previously traveled, and making a wrong turn was not one of my goals. (For a motivational video on making a wrong turn, check this out.) All that was left was to set the alarm for a 4:00 am wake up call.



As usual, when I need to wake up early, I can’t sleep. I wake up every hour on the hour. I felt pretty anxious when I finally decided to get out of bed around 4:15 am. Getting dressed I was feeling stressed and filling my head with self doubt. What was there to worry about? It wasn’t a race. No one was going to be watching. No one even knew I had given myself the challenge to complete the 5 Peaks. Failure was an option. I used the brief drive to the parking lot at Cowles Mountain to calm my mind, nourish my body (banana, Pro-bar, Red Bull, and water), and embrace being in nature.

Once I was parked and had on my gear all of the anxiety I felt just melted away. Official start time was 5:17 AM, and it was a dark, cloudy morning. Feeling excited about the cool temperature, I began running North on Golfcrest Drive.

After a little more running on the road, I made my way into the trail system. After a few rolling hills I encountered my first challenging hill, the Staircase on southern slope of South Fortuna. This hill gains around 700 feet of elevation in short notice. It’s steep and the most technical section of the trail. Knowing this was the first big climb, I took my time and ascended the mountain as the sun began to cast light onto the world. After tagging South Fortuna, it’s a direct, 1-mile shot across the ridge, with another 400 feet of elevation gain to reach the summit of North Fortuna. Two summits down; official time now 1 hour, 18 minutes, and 38 seconds.

Leaving North Fortuna, my legs (and soul) were feeling fresh, and I began to feel very confident about running a fast time. I descended back to the Fortuna Saddle and turned east toward the third peak, Kwaay Paay. The descent down the fire road and through Oak Canyon go by pretty quickly, and I made my way across the Old Mission Dam and started the 1-mile climb up Kwaay Paay. Everything I had heard about this climb was true–it’s short, and very, very, very steep. After climbing 900 feet in 1 mile, I was given the gift of the summit. Three peaks down; official time now 2 hours, 10 minutes, and 18 seconds.

The descent from Kwaay Paay is technical and fast. After the descent there is a 2-mile section of road running headed east on Mission Gorge Road and then turning south on Big Rock Road.

At the end of Big Rock Road, the Big Rock Trail begins, and so too begins the climb up the east side of Cowles Mountain. Around halfway through this thousand feet of climbing my legs began to feel weaker and I realized the sun was taking a toll on me. This was also the first section of trail that I encountered other hikers and runners. I was thankful to see them and welcomed the extra boost in energy. I dug deep, shared some hellos with my fellow adventurers, and harnessed positive spirits from some friendly trail dogs.

All of a sudden I was summiting Cowles Mountain and standing with a large crowd waiting to get their photo taken with the summit sign. I took a picture from afar and set my sight on the final peak. Four peaks down; official time now 3 hours, 24 minutes, and 11 seconds.

I knew I was still at a low point when I left Cowles Mountain. I felt dehydrated, tired, and anxious about the dreaded bonk. With the last peak in sight I just kept my mind on the prize, and filled my body with positive thoughts that I was nearing the end of my journey. Although my trip from Cowles to Pyles was slow, I summited the final peak of the 5 Peaks Challenge. Five Peaks down; official time now 3 hours, 47 minutes, and 34 seconds.

The fun part about the challenge is Pyles is only accessible via the Cowles Mountain trail. That means once you summit Pyles, you turn around and summit Cowles again, so it’s actually a six-peak challenge. Thought you were done? Not yet! Although I was out of water and tired, the boost from having completed the challenge made each footstep a little lighter. It didn’t hurt that most of the way back to the parking lot was downhill.

Fighting the sun and crowds, I made my way to the Cowles Mountain parking lot and my journey was complete. Official time for my car-to-car journey was 4 hours, 31 minutes, and 54 seconds. This was a time I was proud of, and a time that set the stage for me to make another, hopefully faster, attempt on the 5 Peaks Challenge again.



I like to run for a lot of reasons. One of them is for the challenge–both physically and mentally. This was a great reminder that when the anxiety creeps in, it’s best to get out and try. Get on the trail, get into nature, step into the challenge.