From Bucket List to Trailhead: Running the Timberline Loop

Back in 2017, I let myself dream big.

That year, I started drafting a list of 100 dreams—some audacious, others small and whimsical. I never made it to 100, but that was part of the magic: reaching that number forces you to go beyond the obvious. Somewhere in a backpacking guide, I spotted a loop around Mt. Hood—42 miles via the Timberline Trail and a section of the PCT. Something about circling a mountain felt mythic. I wrote it down.

When I made that goal, I wasn’t an ultra-distance trail runner. In 2017, I was coming off the high of bodybuilding and had leaned into cycling. I had just finished my first 100-mile bike ride, and what I was capable of felt more vast than ever.

Fast forward to now: a weekend-long run is easily 4–6 hours, depending on my next event. What used to be the longest distance I had run prepping for a marathon (20 miles) is now a minimum weekend run. I wanted to cross that trip around Mt. Hood off my list—and I wanted to do it as a single run.

The summer of 2024, it just never fit into my schedule. After encountering a mountain lion while running by myself, I felt less comfortable completing the Timberline Trail alone. I wanted my husband to do it with me. I was training for my first 100-miler, Rio del Lago, and the elevation profile was much more conservative, making the Timberline Trail not a very race-specific training route. So I filed it away for 2025.

This year, Sam spent the spring and early summer training alongside me to be ready to complete the loop and pace me at my next 100-miler in August. He was anxious, as this would be his furthest distance. I was slightly less anxious, but I found myself most anxious about his nerves. I am used to coaching myself through tough spots, but when you go with someone else who’s nervous, you sign up for their unknowns as well. What if he couldn’t do it? What if one of us broke an ankle out there? What if I couldn’t do it? There was only one way to find out.

Day Before the Run

We headed to Timberline Lodge on Friday afternoon. There was a lot of smoke in the air, and the high winds made for a nerve-racking trip through the Gorge in our camper. When we arrived at the lodge, the wind was relentless, turning up my anxiety for the following day. We took a short walk to stretch our legs and find the trail. There was a little shortcut trail up to the PCT right next to our parking spot. Then we went into the lodge just to check it out. We had considered staying there, but ultimately decided our camper was an easier (and less expensive) choice. We made our usual long run dinner and settled in for the night.

Saturday Morning

Our alarm was set for 4 AM, but I turned it off and snuggled into Sam where we continued to sleep until 4:38 AM. The wind had kept me awake for much of the night, and the idea of going outside was becoming increasingly challenging. We got up, made some coffee, and worked on getting up the nerve to go outside. It was cold and windy, just as we suspected. Our plan was to start at 5, but obviously that wasn’t going to happen. By 5:30 we decided it was too cold to wear our shorts and sunshirts. So we put on our extra clothing from our packs. This was our first mistake of the day.

About 2 miles into the run we approached our first glacial stream crossing. We managed to find a way across without getting our feet wet, but when we got to the other side, we stopped and took all our extra clothing off and re-packed our packs. The wind seemed to have been lingering at the parking lot but had vanished as soon as we hit the trail. The trail was a bit challenging to locate across the river. It had been washed out, and the downed trees were hiding it, but this was where GPS maps on my Garmin were incredibly handy.

We started our first of many climbs for the day (my Garmin counted 24 climbs, but some of them were really short. I had calculated about 4 significant climbs). This first section of the trail from Timberline Lodge past Mt. Hood Meadows was my favorite. Everything was so green, the wildflowers were abundant, and as we neared our second major water crossing, there were waterfalls everywhere. About 8 miles in, we stopped to fill bottles for the first time at a small creek.

Leaving that creek, the trail abruptly vanished. We did eventually find it, but it was clear that winter had taken it out and we had to climb down a small cliffside. Newton Creek was the most challenging glacial crossing we’d make that day, but not by much. I knew we weren’t supposed to fill bottles with glacial river water, but I was unsure how I would know which was glacial water and what was drinkable creek water—it was obvious. The glacial streams ran fast, and you can’t see the bottom of the creek, making them more difficult to cross, whereas creek water is crystal clear and has a peacefulness about it.

Once we got across, we began our second-longest climb of the day, about 3 miles and 2,000 feet to the highest point on the trail, sitting just above 7,000 feet. We settled in with our poles and power-hiked to the top. The view opened up and it looked as though we were headed to the top of Mt. Hood (we weren’t), then off in the distance, you could see Mt. Jefferson to the left, and Mt. Adams to the right. As we made our way counterclockwise around Mt. Hood, we lost sight of Mt. Jefferson but could now see Mt. Rainier and Mt. St. Helens as well. There was rarely a moment without a breathtaking view.

As we continued to near the high point, we crossed big snowfields. I did my best not to look down at where I’d land if I lost my footing. Having poles through this section was incredibly handy. We ran into several backpackers in this section—naturally, as it was the worst place to pass people since everyone wanted to use the footprints in the snow to avoid slipping.

Traversing down the mountain after hitting the high point was slow, as the trail was rocky and technical. Eventually, it did become more runnable. This section continued to be one of the most high-traffic areas of the day—and the driest.

Eventually, we made our way to the bottom of a canyon where we came to another glacial river crossing—the only one with a bridge (four logs tied together with climbing rope). Immediately after crossing, we had to climb right back out of the canyon on a gravel and rocky slope. The slope had three climbing ropes anchored between two boulders above. Nervous about whether I should trust them, Sam told me to give it a good tug. The most challenging part was holding my poles while trying to use the rope. It would have been easier to put my poles away and use the rope to get to the top, but I didn’t fully trust the ropes and wanted to use my poles as backup.

From there, we kept traversing along the mountain. We stopped at one point to shake more gravel from our shoes. I’m not sure at what point we forgot to throw gaiters into our pile of gear, but I think they would have been helpful. I was struggling with my shoes—on the heel, there was a spot where gravel would collect between the shoe and my heel rather than dropping into the shoe. This caused rubbing and I constantly felt like I was making a hot spot. Luckily, it never became something more.

I’d packed for this trip like I would any other long run or race, but if I were to do it again, I would pack a little more “backpacking” food—i.e., more real food and fewer gels. Because we were moving at a lower intensity than most of my runs, I could have digested real food and felt more satisfied. We stopped 5–6 times to refill bottles throughout the day using our Katadyn filters. I added Skratch or Tailwind to most of my bottles but did have plain water a couple of times.

Our least favorite part of the trail was miles 24–30. This section had a lot of downed trees (I renamed the trail the Timberdown Trail) and heavy overgrowth—particularly marionberry bushes, which were very scratchy. I reminded Sam of the beauty we were witnessing and kept reminding myself there was nothing I would rather be doing. We were also now out of water and in need of a fill-up.

At mile 30.7, we hit Ramona Falls. I knew this was a big deal because we were now headed in the direction of the lodge. I was hoping we were officially in the single digits (we weren’t) as far as miles remaining. We stopped at the falls to fill bottles, and I decided to change my socks. I knew they were unlikely to stay dry, but my toe socks had collected little rocks and sticks. Even when I shook out my shoes, things were embedded in my socks. Clean socks felt so nice. We ate a beef stick and some trail mix. We were headed into the section I had been most anticipating all day.

We crossed our last major glacial river crossing, which was out in the open, making it very hot. It was the first time all day I felt nauseous and a little bit dizzy. Now we were back on the PCT and starting our longest climb of the day—3.7 miles and 2,200 feet. This climb wouldn’t generally feel hard. It’s a distance and grade I’ve trained on a lot, but at that point in the day, I was struggling. I hit a mental low, unsure about all the other running goals I had on the calendar. I kept taking inventory of my body: knees, hips, hamstrings, feet—all the usual suspects felt fine. Nothing was hurting. What I wanted was to close my eyes and go to sleep. I even said to Sam, “Maybe I need to try out one of those dirt naps.” What kept me going was that I didn’t want to finish in the dark. I wanted us to hit our 14-hour predicted finish. But it was a slog.

We passed several backpackers: three young men sitting on the side of the trail looking spent, a lone female hiker struggling with the heat. “This is the most solemn section of trail we’ve seen today. Everyone looks defeated!”

When we did finally reach the top, the downhill hardly resembled running. I could tell Sam would prefer to walk, so I alternated running and hiking. Running was the fastest way to finish, so I didn’t give up on it. We still had a little more than 4 miles to go at the top of that climb, but we didn’t really know exactly how much was left. The trail on Strava lists it as 38.7 miles, but I think all the wandering around to find river crossings and lost trails adds up—most people report between 41–42 miles.

The best feeling was when you could see the face of Mt. Hood we had camped under. We could see ski lifts in the distance and day hikers wandering around without packs. We were almost there.

As soon as we had the lodge in sight, the wind picked up and it was cold all over again. The next morning when we stepped out into the wind, I was convinced the parking lot had the worst weather of the entire trip.

Throughout the day I kept thinking about how insane it was that I once feared completing this trail over 3 days—and here I was doing it in one. The person I was when I completed my first ultramarathon in 2021 wouldn’t recognize the runner I am today.

This trail humbled us, sure, but it was within our skillset. We needed a good humbling. Every runner does. Each run builds you up a bit more for the next. During that last long climb on the PCT, I began removing bucket list races from my list. No way am I ready to do UTMB or the HURT 100.

While texting my coach Anne the next day, I said, “Maybe I forgot during that moment that I’m not supposed to be ready to do those things right now. The point of training is to prepare for the bigger goals.”

Thank goodness for good training and an able body.

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