Looking west from the summit.

• Located in San Carlos, this trail is an easy to moderate hike. With a length of 3 miles up and back, and an elevation gain of just under 900 feet, the hike will take most people an hour and a half. Leashed dogs are allowed, but not encouraged on a warm day.
• Distance from downtown San Diego: 15 miles
• Hike length: 3 miles • Difficulty: Easy to Moderate • Season: Year-round

“Sorry I’m late,” I said, stepping over the gate separating the dusty trail from the road.

“Not a problem,” replied my friend, Dean. “I was just walking over to see if you were parking.”

I gave him a big bear hug then broke away. Dean paused, as if considering what to say next, then said, “I was actually telling Kara how punctual you usually are.”

“Used to be,” I said, glancing ahead of me where Dean’s girlfriend was standing, partially obscured by the shadow of the trail kiosk. Not knowing her, I wondered if she was the type of person who scorned people who were late and whether she disliked me already.

“But then I read that punctuality is the thief of time and now I’m late on principle. And it’s Kara?” I asked Dean in a hushed tone.

“Yep, Kara,” he confirmed.

With a warm smile I walked up to Kara and held out my hand. “Hi, Kara. I’m Ryan.”

“Hi. Nice to meet you,” she said, shaking my hand with a friendly smile.

“You two ready to climb San Diego’s most popular mountain?” I asked, bending over to give my hamstrings a stretch.

Profile of cowles from pyles peak.

Dean and Kara glanced at one another. Neither seemed overly enthusiastic. Dean looked slightly eager. Kara, not so much. She had an uncertain look on her face, as if she had expected a flat hike on a brisk day.

“Yep. Let’s do it,” said Dean.

We chatted idly as we headed toward the mountain until the trail forked ahead of us. Turning to Dean and Kara, I said, “Alright, we have two choices. We can either go up the switchbacks,” I paused to point at the half-dozen hikers snaking along the switchbacks to my left, “or,” I continued, pointing to the steep trail on the right, “we can take the fire road, which is steep, level, and then steep again.”

Dean and Kara glanced at one another with a look that seemed to say, “It’s too early to make a decision.” Not wanting to influence them, I let the question hang in the air. Taking non-hikers up the backside of Cowles was a longstanding tradition for me, and I enjoyed seeing which path my companions chose. I found that the decision revealed a certain quality of character.

Dean looked at the switchbacks. Kara looked at the fire road. Then they looked at each other.

“Let’s do the switchbacks,” said Kara.

“Agreed,” said Dean.

“Sounds good,” I replied, mentally tallying their choice alongside the other hikers who had made the same decision in years past.

Dean led the way up the trail, setting the pace. He was a high school friend I hadn’t seen in six months, which was about how long he and Kara had been dating. We chatted and traded stories for the first few switchbacks, but being mindful of how self-absorbed two old friends can be when they catch up, I tried to keep the conversation interesting for Kara. As she told me about her life, I noticed her gasps for air took longer and longer, until I got the distinct impression that I was torturing her with a barrage of personal questions; which was probably not the most enjoyable thing to do while making hairpin turns up the side of a mountain. Not wanting to make the hike a completely unpleasant experience, I took the lead from Dean and adjusted my pace, taking deliberate half-steps up the trail to slow us down.

As we completed the first set of switchbacks, I noticed that Dean was also taking longer to respond, so I took the initiative to carry the conversation by sharing amusing stories. In truth, it had been some time since I hiked with others, and I even found it somewhat challenging to chat and climb. Of course, I have a hiking reputation to uphold, so naturally I pretended not to be winded at all – although I doubt anyone fell for my act. 

The morning sun was climbing higher, bringing with it a dry heat. A distant brush fire to the north scented the air with a pleasant, campfire aroma, though my weary lungs strongly disagreed and burned like smoldering embers. It was bustling as we merged onto the frontside of the trail. Despite the crowd, there were only a few “good mornings” or any other pleasantries from passersby.

Sunset on cowles while looking east.

The more switchbacks we climbed, the less conversation we made. Though she persevered without complaint, Kara was starting to burn out. Having seen this situation unfold many times before, this was typically the moment in which a less experienced hiker would say something encouraging like, “we’re almost there” or “the top is just behind that point.” I, however, bit my tongue and said nothing whatsoever. Dean was not so wise. And in an attempt to reassure his girlfriend, he turned to her and said, “We’re almost there, it’s just beyond that peak, babe.”

Not wanting to be in the way of what was coming, I stepped to the side and as if on cue, Kara brusquely replied, “Well, I’ve been staring at that point and it’s not getting closer – babe.” The sizzle in her voice could have fried an egg.

Well, nothing like a steep hike on a hot day to test a new relationship.

Before Dean could finish digging his grave, I stepped in. “You’re both right. That’s a false peak. But the real one is close behind it, just a few more switchbacks.”

Soon after, we reached the peak and Kara sought refuge in the shade of a nearby boulder. As her and Dean’s flushed faces drained to their natural hue, I took a photo of the happy couple on the summit. After a few good shots, Dean and Kara turned around to glance at the distant mountains in the east.

“Since everyone's moved away, these have become my new friends,” I said, affectionately extending my arms toward their hazy silhouettes. Dean and Kara looked at the mountains with mild interest, as if they were vultures eyeing a clean skeleton. Their attention seemed to wane. I felt a bit disheartened.

Rather than retracing our steps, we cautiously descended the fire road with only a couple of minor slips on the loose gravel. Dean and Kara became much livelier on the way down. As I bid farewell to the two of them at the trailhead, I felt grateful for their willingness to cross into my world. Hiking, like so many other endeavors in life, may first appear as a daunting task, but it gradually transforms into a welcoming companion through familiarity and experience.