Skyline Trail – A Love Story

Looking east over the Kenai Peninsula, from the top of Skyline.

Skyline is one of those trails that instills a subtle intimidation in your soul when you first hear people talk about it; an intimidation that screams of irresistible challenge. A few years ago when I got into hiking, I had that feeling. Being out-of-shape and just getting my hiking legs, I knew Skyline would be too physically-demanding for my rookie-self. I hike other trails. Smaller ones. Less-strenuous ones. Those without as much intimidation factor. All the while, though, I was going on progressively difficult treks — consciously and subconsciously preparing for Skyline.

If at first you don’t succeed…

The first time I went after Skyline, it was just me and my dog, Diesel. It was early on a Friday morning and the parking lot was empty when I arrived at the trailhead. At that point, my concern drew away from the physical nature of the trail and towards the recognition of a few important facts: I was in bear country, at a time of day when they are most active and moving about, and no one else was already on the trail making noise, persuading the bears to disperse. I decided to make a go at it anyway.

At the beginning of the trail, I immediately noticed the sign of bear activity: tracks at the trailhead, and just a little bit further, a tree with deep scratches (bears commonly exhibit a behavior in which they essentially use a tree as a scratching post, possibly as a way of marking their territory in warning to other bears). Still, I wanted to push forward. About a half-mile in, my normally-complacent Diesel seemed a bit on edge. He was acting much more aware of his surroundings and exhibited a certain alertness. I was a little concerned as to how he would react in a situation with a bear. Would he go on the offense and try and chase the bruin away? Would he stand by my side, possibly antagonizing an attack? Or maybe he would just take off and leave me to fend for myself (there’s a common joke for those that travel into bear country, you don’t need to be able to run fast to escape a bear attack… just faster than the slowest person you’re with). I wasn’t quite sure that I wanted to find out, and when I heard some thrashing in the alders just ahead of me on the trail, I was quite sure I did not. Somewhat disappointed with myself, I turned back and called it a day.


My next go at the trail came a week or so later. This time I was with a group, it was midday (bears are generally more active in the mornings and evenings), and the trail had a fair bit of traffic. Nothing was going to stop me this time… until I took a bad step and rolled my ankle. I knew right away that I overexerted my ankle, not because of the pain – in fact, at first it didn’t hurt at all – but due to the sudden rush of blood that went to my foot. It felt warm and… almost pleasant. But I knew it was a harbinger of a less-than-pleasant rest of the journey. Regardless, I intended to continue. I encouraged the rest of the people in the group to continue on ahead of me and go at their own pace. They were in much better shape than me anyhow and could probably have reached the peak and met me back down at a saddle area between the peaks. For whatever reason (kindness to a fault?), they refused to go ahead without me. They argued that we should head back down the trail before my ankle really started hurting; which I wouldn’t admit was already starting to happen. I was adamant about continuing on. We compromised on continuing just up to the saddle area and not attempting the peaks above. We reached that point and though I wanted to continue limping my way further, it was clear that the rest of the group was ready to go back; I dropped my persistence and followed them back down. On the plus-side, this was the furthest I had made it up the trail and the views were already breathtaking at that elevation.


A third attempt was another solo trek. I was very limited on the time I had and mainly just wanted to use the trail as an opportunity to get my heart-thumping and calves burning, not necessarily to ascend to the top. There were enough people on the trails to keep me unworried about bears, but few enough that I truly felt the peace of solitude as I climbed. I continued on past the saddle area and started poking my way around the rocks towards a ridge that leads to the “top’” (really, the trail ends at the saddle but there are various other footpaths through the rocks that lead up the rocky ridge to the highest peak adjacent to the trail) of the trail. If I was focused on reaching the peak, I could have done it in the time I had, but I chose instead to do a little exploring around the ridges before heading back down. I spent the rest of the season on other trails, never having made it to the top that year.

Again (Finally)

It was a year later when I climbed that trail again. This time, my wife agreed to come along. It was early in the hiking season, and after a winter of hibernation neither of us had the cardio to relentlessly scramble up the mountain. But we did have plenty of determination and encouragement for each other. For a fair bit of the trail, you can look up and to the east and see the ridge leading to your ultimate destination. Your perceptions can be deceiving – the apparent distance to the top of that ridge seems to grow exponentially with how winded you are when you look at it. And even though there were times when my wife and I both probably wanted to call it a day, neither would admit it at the same time. Our mutual stubbornness kept us going. I remember saying, “We’ve done a good job and seen some amazing things along the way… if we turned back now I’d still feel a sense of accomplishment!” She wouldn’t bite, so we went on. And on. And on… until we were on a rocky ridge above a field of snow, reaching ever closer to the peak above. One foot forward, then the next to pass it. And then, we were there. While the view to the south that we had most of the hike was spectacular, the new view we had to the north was utterly breathtaking.

Jan looks over the Kenai Mountains to the north.
Jan looks over the Kenai Mountains to the north.

We had done it and our reward was two-fold. For one, we accomplished the tangible. We set out to reach a challenging destination, we persisted, and we accomplished that goal. Our other reward was the journey itself. We learned that the biggest percentage of the difficulty was mental and practiced our abilities of willing our minds to keep putting one foot in front of the other. We learned that we were better together than we were alone (pardon the cliché, but the sum was truly greater than its parts).

Stomping grounds…

Since that ascent, I’ve hiked Skyline a handful of times again. It’s the kind of trail that really doesn’t get old. In fact, I find that the trail grows on me. The scenery changes depending on the weather and the seasons and never ceases to amaze. Skyline was like my first real mountain crush. I was at first attracted, mustered the courage to approach, and was finally accepted (after some initial rejection!). As a result, Skyline will always hold a special place in my heart.

Orange box containing the logbook.
The orange box located in this cairn contains a logbook to prove your accomplishment.

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