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5 Peaks of Mission Trails

"I faced my limitations, which gave way to an expanse of emotions"

Standing atop a foggy Cowles mountain.
Standing atop a foggy Cowles mountain.
  • 5 Peaks of Mission Trails
  • Located in San Carlos, the 5-Peak Challenge is a very strenuous hike. With a length of 17 miles and an elevation gain of around 4,300 feet, the hike will take most people 6 to 9 hours if they try in one day. Dogs are allowed but not recommended.
  • Distance from downtown San Diego: 13 miles
  • Hike length: 17 miles • Difficulty: Very strenuous • Season: Year-round


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I was sitting on South Fortuna Peak, picking the mud out of my trail runners with a stick, when I heard a voice from behind me ask, “Are you doing the 5-Peak Challenge, son?”

I pulled out an earbud and spun around to see an elderly man with a white beard and a wide-brimmed hat, leaning on his trekking poles. His face was rosy and his eyes friendly.

“I am,” I said with a grin. “What gave it away?”

“Well, your clothes are soaked, and you got more mud on you than a wild hog.”

I looked at the back of my legs, which were flecked with specks of clay, then laughed. “Yeah, I’m doing the challenge in one go by foot.”

“At once? Well, that’s quite the endeavor.”

“Thank you,” I said. “I know these peaks pretty well and wanted to ring in the new year with a challenge.”

“That’s as good a reason as any,” said the man. “I did the challenge myself a few years back, but over the course of a few months.” He nodded to the 5-Peak Challenge pin that was hanging off his backpack strap. It looked exactly like the one I had in my desk drawer.

“Well, it’s not a race,” I replied. “What matters is that you enjoy doing it.”

The man nodded, and his eyes seemed to twinkle. Then he asked where I started my hike.

Looking at the tower on Cowles.

I pointed at Cowles Mountain and said, “On the backside at the Barker Way Trailhead. I went up the fire road to avoid the crowd. Then I jogged over to Pyles Peak before turning around and heading down the frontside of Cowles.”

“How far is that?” he asked.

“Oh, a little under six miles, with an elevation gain of just under 2000 feet.”

A breeze twirled by and a thin ray of light peered through the clouds. “And how many peaks do you have left?” he inquired.

“One. From Cowles, I jogged past the Visitor Center along Father Junipero Serra until I got to the dam. Then I went up Oak Canyon to the Fortuna Saddle and hiked straight to the top of North Fortuna. I decided it would be easier to do that third, since it was a steeper incline. Then I turned around and crossed the saddle to get here.”

A quiet Father Junipero Serra road.

“That’s what, another eight miles?” he asked.

“About seven. But the elevation gain isn’t as steep, it’s only 1400 feet or so.”

“And now you only have one more to go,” he said while turning to look across the valley toward Kwaay Paay (kweye pie) Peak. We chatted for a bit longer, but my knees were starting to stiffen, so I got up to signal that it was time to go. The man offered to snap a photo of me on the peak with my phone, which I agreed to; then I thanked him and said goodbye before going on my way.

Me on South Fortuna, photo by the old guy.

It was a gray day and the trail was slick. Winter had just arrived, but a hint of spring was beginning to poke through the earth, thanks to the recent rainstorms. I had walked back to the Fortuna Saddle and was peering down the long sloping path before me. It was steep and muddy, and I was concerned about my tired feet, which had grown cold and numb while resting on South Fortuna. Burdened by fatigue, I took one cautious step down the muddy hil,l then another. The effort was slow and tedious, but I arrived at the bottom without incident — only to suddenly lose my footing and fall flat on my face.

Sitting there like a worm in the mud, I sat and wondered whether I should just give up, when beside me, I saw a tiny blade of grass sticking through the soil. It stood against the breeze, reaching for the sun, and in my exhaustion, I could hear it cheering me on in a soft voice. I sat there a while longer without grace or pride, watching the clouds roll in, then I picked myself up and wandered into Oak Canyon like a tired coyote limping into the brush.

There I met a shallow stream that I walked alongside before stopping at a small waterfall to wash myself. Some kids ran over and began splashing around below me in a swimming hole. Their parents clutched their coffee cups with concern and hissed at the kids to not get too close to me. As the mud washed off me, I flashed the parents an amused smile before starting on the path again in a light jog, gliding over wet stones and passing under century-old oak trees. The sound of my footsteps was muffled by damp leaves, and a fine mist obscured the path. Hikers drifted by with wonder on their faces as they took in the canyon’s beauty.

Looking up at Kwaay Paay.

Passing the Old Mission Dam, I lifted my tired eyes up to Kwaay Paay, its peak hidden in the clouds. Chaparral lined its steep hills, out of which I saw the trail spooling like a winding ribbon. I did not feel intimidated. Instead, my heart grew light and I greeted my old friend once more with renewed strength. Years of hiking up the mountain had led to familiarity, then affection, and finally deep respect.

I had climbed Kwaay Paay hundreds of times, until it was no longer a place to visit, but a constant beacon of light that helped me weather the storms of my life. Like a ship seeking a lighthouse, I was drawn to the peak because it allowed me to navigate the currents of my life more clearly. With each ascent up the mountain, I faced my limitations, which gave way to an expanse of emotions ranging from frustration to joy. As I grew stronger, the emotions became more subtle and complex, and over time, I began to distinguish these delicate feelings, until I saw them as a series of bewildering colors that collided and splintered across an endless spectrum of light — and that no one color defined me.

The mountain became a torch to guide me, and gradually, I began to see that its light wasn’t constant, but flickered with its own subtleties. The more I gazed into this ever-burning flame, the more I saw that it too consisted of a tapestry of colors that changed with every passing day, through every passing season, from the sweltering summer at sunset to the freshness of spring at sunrise, and that like me, the mountain was entangled from beginning to end in its own colorful threads of light; until at last I understood that all those pretty colors were the sum of one light that had hidden itself in a sea of beautiful moments, as if they were shining through a glass prism. Many of those moments I had seen, but I knew there would be many more that I did not. And as I stood on the frontier of my awareness and peered into oblivion, I wondered what beautiful and fiery sunrises and sunsets the mountain had witnessed across the seasons of my life that I had not the sight to see.

When I reached the peak, the mountain evoked a new color and I was embraced by a silent sorrow; the kind which you can find on the last page of a good book. My challenge was done. I didn’t fall to my knees with tears of joy, and no one patted me on the back. Instead, my knees throbbed, my shoulders ached, and my legs quivered. The adventure was over, so I turned around and let the mountain guide me home.

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Standing atop a foggy Cowles mountain.
Standing atop a foggy Cowles mountain.
  • 5 Peaks of Mission Trails
  • Located in San Carlos, the 5-Peak Challenge is a very strenuous hike. With a length of 17 miles and an elevation gain of around 4,300 feet, the hike will take most people 6 to 9 hours if they try in one day. Dogs are allowed but not recommended.
  • Distance from downtown San Diego: 13 miles
  • Hike length: 17 miles • Difficulty: Very strenuous • Season: Year-round


Sponsored
Sponsored

I was sitting on South Fortuna Peak, picking the mud out of my trail runners with a stick, when I heard a voice from behind me ask, “Are you doing the 5-Peak Challenge, son?”

I pulled out an earbud and spun around to see an elderly man with a white beard and a wide-brimmed hat, leaning on his trekking poles. His face was rosy and his eyes friendly.

“I am,” I said with a grin. “What gave it away?”

“Well, your clothes are soaked, and you got more mud on you than a wild hog.”

I looked at the back of my legs, which were flecked with specks of clay, then laughed. “Yeah, I’m doing the challenge in one go by foot.”

“At once? Well, that’s quite the endeavor.”

“Thank you,” I said. “I know these peaks pretty well and wanted to ring in the new year with a challenge.”

“That’s as good a reason as any,” said the man. “I did the challenge myself a few years back, but over the course of a few months.” He nodded to the 5-Peak Challenge pin that was hanging off his backpack strap. It looked exactly like the one I had in my desk drawer.

“Well, it’s not a race,” I replied. “What matters is that you enjoy doing it.”

The man nodded, and his eyes seemed to twinkle. Then he asked where I started my hike.

Looking at the tower on Cowles.

I pointed at Cowles Mountain and said, “On the backside at the Barker Way Trailhead. I went up the fire road to avoid the crowd. Then I jogged over to Pyles Peak before turning around and heading down the frontside of Cowles.”

“How far is that?” he asked.

“Oh, a little under six miles, with an elevation gain of just under 2000 feet.”

A breeze twirled by and a thin ray of light peered through the clouds. “And how many peaks do you have left?” he inquired.

“One. From Cowles, I jogged past the Visitor Center along Father Junipero Serra until I got to the dam. Then I went up Oak Canyon to the Fortuna Saddle and hiked straight to the top of North Fortuna. I decided it would be easier to do that third, since it was a steeper incline. Then I turned around and crossed the saddle to get here.”

A quiet Father Junipero Serra road.

“That’s what, another eight miles?” he asked.

“About seven. But the elevation gain isn’t as steep, it’s only 1400 feet or so.”

“And now you only have one more to go,” he said while turning to look across the valley toward Kwaay Paay (kweye pie) Peak. We chatted for a bit longer, but my knees were starting to stiffen, so I got up to signal that it was time to go. The man offered to snap a photo of me on the peak with my phone, which I agreed to; then I thanked him and said goodbye before going on my way.

Me on South Fortuna, photo by the old guy.

It was a gray day and the trail was slick. Winter had just arrived, but a hint of spring was beginning to poke through the earth, thanks to the recent rainstorms. I had walked back to the Fortuna Saddle and was peering down the long sloping path before me. It was steep and muddy, and I was concerned about my tired feet, which had grown cold and numb while resting on South Fortuna. Burdened by fatigue, I took one cautious step down the muddy hil,l then another. The effort was slow and tedious, but I arrived at the bottom without incident — only to suddenly lose my footing and fall flat on my face.

Sitting there like a worm in the mud, I sat and wondered whether I should just give up, when beside me, I saw a tiny blade of grass sticking through the soil. It stood against the breeze, reaching for the sun, and in my exhaustion, I could hear it cheering me on in a soft voice. I sat there a while longer without grace or pride, watching the clouds roll in, then I picked myself up and wandered into Oak Canyon like a tired coyote limping into the brush.

There I met a shallow stream that I walked alongside before stopping at a small waterfall to wash myself. Some kids ran over and began splashing around below me in a swimming hole. Their parents clutched their coffee cups with concern and hissed at the kids to not get too close to me. As the mud washed off me, I flashed the parents an amused smile before starting on the path again in a light jog, gliding over wet stones and passing under century-old oak trees. The sound of my footsteps was muffled by damp leaves, and a fine mist obscured the path. Hikers drifted by with wonder on their faces as they took in the canyon’s beauty.

Looking up at Kwaay Paay.

Passing the Old Mission Dam, I lifted my tired eyes up to Kwaay Paay, its peak hidden in the clouds. Chaparral lined its steep hills, out of which I saw the trail spooling like a winding ribbon. I did not feel intimidated. Instead, my heart grew light and I greeted my old friend once more with renewed strength. Years of hiking up the mountain had led to familiarity, then affection, and finally deep respect.

I had climbed Kwaay Paay hundreds of times, until it was no longer a place to visit, but a constant beacon of light that helped me weather the storms of my life. Like a ship seeking a lighthouse, I was drawn to the peak because it allowed me to navigate the currents of my life more clearly. With each ascent up the mountain, I faced my limitations, which gave way to an expanse of emotions ranging from frustration to joy. As I grew stronger, the emotions became more subtle and complex, and over time, I began to distinguish these delicate feelings, until I saw them as a series of bewildering colors that collided and splintered across an endless spectrum of light — and that no one color defined me.

The mountain became a torch to guide me, and gradually, I began to see that its light wasn’t constant, but flickered with its own subtleties. The more I gazed into this ever-burning flame, the more I saw that it too consisted of a tapestry of colors that changed with every passing day, through every passing season, from the sweltering summer at sunset to the freshness of spring at sunrise, and that like me, the mountain was entangled from beginning to end in its own colorful threads of light; until at last I understood that all those pretty colors were the sum of one light that had hidden itself in a sea of beautiful moments, as if they were shining through a glass prism. Many of those moments I had seen, but I knew there would be many more that I did not. And as I stood on the frontier of my awareness and peered into oblivion, I wondered what beautiful and fiery sunrises and sunsets the mountain had witnessed across the seasons of my life that I had not the sight to see.

When I reached the peak, the mountain evoked a new color and I was embraced by a silent sorrow; the kind which you can find on the last page of a good book. My challenge was done. I didn’t fall to my knees with tears of joy, and no one patted me on the back. Instead, my knees throbbed, my shoulders ached, and my legs quivered. The adventure was over, so I turned around and let the mountain guide me home.

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