The Timberline Trail (1/5)
Well, here we go. This is the big one.
Going into this past summer, I had big plans. I mean, I always have big plans, every summer. But I'd plotted out ideas for lots of brand new hikes this time: in southern Idaho, in the Sierra, in the north Cascades.
And of course, as is the way of things every summer, nature (and wildfires in particular) had other plans.
Long story short, I did not anticipate that my biggest hike of the season would be on a trail that I'd already hiked (and nearly drowned on) in 2019, and had you told me that in June, I would have been disappointed to hear it. But then, with the beginning of the academic year looming, circumstances made the Timberline Trail my only good option for a long September hike, so I took it. And it was amazing.
Back when I'd first done the Timberline in 2019, it had been with Lindsey, and at that point it had been the most difficult and complicated backpack we'd ever done together. We did it in early August, and that meant lots of green on the trail, snow on the mountain, and wildflowers everywhere, but it had also made some of the creek crossings legitimately scary. I'd be doing the Trail solo this time, and while I knew doing it in September would make those crossings safer, I also wondered how the rest of the experience would change, on the cusp of fall.
On September 16th, I made the long drive up from Klamath Falls to the Timberline Lodge to find out.
While the Lodge is arguably the most efficient place to start the loop from, I get why folks start from more remote trailheads: Timberline Lodge is a weird place to start a five-day backpacking trip from. Most of the people in the parking lot when I arrived were there to spend the night in the Lodge itself and/or get pictures of themselves with Mount Hood in the background by just stepping out of their cars. Not that there's anything wrong with any of that, but I felt like I stood out like a sore thumb as the only grizzly, gear-laden weirdo crossing the parking lot to the big PCT sign.
The Timberline is another one of those trails where the clockwise-versus-counter-clockwise decision is a weighty one. That said, in this case I only very briefly considered it. We'd gone clockwise in 2019, it was the way I knew, and I wasn't interested in introducing too many new variables to my hike this time around. If I ever do the Trail again, I'll likely go the other way around for variety's sake, but this time I wanted to at least mostly stick to what I knew.
So, from the Lodge it was west below the southern face of Mount Hood for me.
For the first half-mile or so, the PCT takes you under a few ski lifts while remaining basically flat, giving you a chance to get your legs warmed up while taking in your first views of the mountain.
Shortly after, things get hilly, and stay (at best) that way for pretty much the rest of the hike.
In fact, the Timberline reminds me a lot of some of my favorite hikes in the Trinity Alps due to the amount of time you'll spend either hiking uphill or downhill. This is, of course, an effect of the fact that you're circumnavigating a mountain, but that emotionless, logical fact of geology isn't much comfort after you've spent a full day (or two, or three) climbing down into a valley, crossing a creek, and then climbing back up the other side of the same valley over and over and over again.
The very first such descent-then-ascent on the clockwise route is a pretty minor one that takes you over the Little Zigzag River. In September, there wasn't even a river anymore, just dust...a lot of which I kicked up as I passed through.
About a mile after this first "crossing," I reached the first of many huge views of the glacier- and water-carved flanks of Mount Hood. This one is from the eastern edge of Zigzag Canyon.
I'd only been hiking for a short time at this point, but I decided to take a nice long break here to properly absorb the view. The mountain was certainly less snowy than the last time I'd been on the Timberline, but it was no less awe-inspiring for that. The immensity of the landscape is one of those things that photographs just can't capture.
It's a little intimidating to look down from such a height at the tiny ribbon of water tumbling along the Canyon bottom below and know that at some point soon, in some way, you need to get all the way down there and then afterward get back up and out...but that's sort of the whole ballgame on the Timberline, so not for anywhere near the last time I sucked it up and started a knee-rattling descent.
Once you've passed the view from the rim of the Canyon, the dayhikers thin out and pretty quickly disappear completely. By the time I reached the bottom of Zigzag Canyon they were gone completely, and the only people I would see for the rest of the day were other backpackers.
The Zigzag River was still flowing, albeit weakly. It made for an easy crossing after I took a short water break.
I noted one small-but-cozy camp spot right up against the river, but I had my heart set on camping at Paradise Park, so I noted said spot for later and started climbing back up and out of the canyon.
The good news was that from here it was only two miles to Paradise Park. The bad news was that I had to climb thirteen hundred feet over those two miles.
I've done this climb twice now, and both times the first half-ish wasn't bad at all. Eventually, though, you reach an intersection and have to choose between going left and staying on the PCT or going right and continuing to climb up to Paradise Park. Both times I've gone right because both times I wanted to camp at Paradise Park. And though the trail you follow to get there is beautiful (hence the name), it really feels like a grind. Maybe it's the sun exposure, maybe it's the steepness, I don't know. But it was a miserable climb the first time, and the second time wasn't any better.
As I grumbled to myself about the heat and the elevation gain, Hood loomed up ahead, presumably sitting in silent judgment of my moodiness.
Eventually, once you've gained most of the necessary altitude, the trail resumes traversing across the slopes rather than climbing up them, and the "Paradise" part of Paradise Park really comes into view.
The Park, too, was a little drier and certainly less full of wildflowers in September than it had been in August six years before, but I was very happy to be back.
I'd arrived a little earlier than I'd planned, and so I took the luxury of dropping my pack and wandering around, trying, as usual, to find The Best Camp Spot Possible. This also gave me a chance to enjoy the non-Hood-centric views out across the western hills.
There are a lot of nice flat spots with mind-boggling views in Paradise Park, but during Lindsey and I's previous trip around Hood we'd learned the peril of these super-exposed sites when we'd casually taken one and then been woken up in the middle of the night by a windstorm smashing the wall of our tent in. This time around, I was going to eschew the views in favor of a more protected spot.
Eventually, I found one tucked nicely below (behind?) the ridge, and though I couldn't see Hood from my tent, exactly, a short walk revealed a nice area for cooking dinner with a view that I would call "pretty damn good."
The waterfall dropping off of this cliff was audible from my tent, as well, and any night I get to fall asleep to the sound of rushing water is a good night. I was pretty stoked.
Before fully settling in for the night, though, I made sure all of my gear was safely stowed away and then headed back up the trail (and uphill) to the main Paradise Park trail to watch the sunset from the ill-fated spot Lindsey and I had camped at back in 2019.
As Hood came back into sight, I was greeted with some great alpenglow.
Then, I made my way over to "our" old tent spot, sat on a log, and watched the sun set while I chewed on a CLIF bar.
I was happy to end the day knowing that I wasn't going to get woken up in the middle of the night by a windstorm folding my tent over.
Once the sun's show was over, I made my way back down the hill, cooked up some dinner in the near-dark, and was in bed just in time to be able to avoid having to use my headlamp at all.
It had been a great first day, and a great start to my second trip around Mount Hood, but of course the first day was also both the shortest and the easiest one of the five. Day two would turn out to be more...interesting.














