The Timberline, a 66 km trail that circumnavigates Mt Hood in Oregon. Situated about an hour SE from Portland the trail starts at the Timberline Lodge at the base of the ski hill and slowly ribbons its way around the mountain exposing all its nooks and crannies in spectacular fashion. Parts of the PCT intersect and piggy back the trail here before branching off again. The trail attracts many hikers each year as a destination multiday hiking route due to its stunning exposure to some classic Pacific Northwest landscape.

About five years ago my friend Tristan and I were down at Mount Hood on a climbing trip and it’s lasting memory sparked an ambitious new idea. A “one day” all in assault around the mountain. As novice trail runners we were familiar with running 20, or even 30km in a single go. But could we do this?

The plan got rattled around amongst a few friends that would actually entertain taking this on. “Hey guys we have this simple idea, drive down to Oregon, run from the middle of the night until when the sun goes down again, 65km around a mountain trail.” What could go wrong?

In the end five of us were convinced that a) we could definitely all start this run, and b) we could definitely maybe finish this thing… maybe?

Myself, Tristan, my brother Isaac, cousin Ryan, and good friend Jason took the plunge.

We chose the middle of July 2023 to maximize our daylight (as we would need every minute of it). The weather was likely to be consistently dry. It would be hot (which would be another challenge to contend with) but dry.

We spent the coming months researching the terrain, watching YouTube videos, testing our endurance on the local trails all in an effort to not completely suck at what we were about to take on.

July came quickly and before long we were packing our bags for Oregon. We now also had some reinforcement as Ryan’s wife Julia and daughter Annika were coming along to crew for us at the 40km mark. We all made our way down the coast from Vancouver BC except Tristan, who was coming direct from Kelowna and would be intercepted at the airport along the way. We arrived at Government Camp, the mountainside town sitting at the bottom of Mt Hood around 4pm. We unpacked our gear and decided a light trail run might be good after a day of travel, and maybe a chance to calm the nerves a bit. We ran a fun 5km route through some single track routes on the outside of town before grabbing some much needed dinner.

Back at the cabin post dinner the reality was sinking in that we were merely a few hours away from embarking on our challenge. The energy was a mix of excitement, nervousness, and some definite “what are we getting ourselves into here” type vibes. We had a final discussion about how much calories to carry, ensured the satellite beacon was connected to Julia’s phone properly so in the event of any trail side emergencies we could get word to her, and organized all our gear into the running vests. We all crashed out pretty early that night as 2am would come quickly.

The alarm goes off. We are all already awake, waiting for it. The house is quiet. We go about making a quick meal, taking in what calories we can and pile downstairs to get ready to go. As we were getting our shoes on and grabbing our vests and poles there was little conversation, the feeling I imagine is similar to a group of skydivers in a plane awaiting their turn to jump. Mentally going through the motions of what is to come. We head the door and climb into the car. It is a short 10 minute drive to the Timberline Lodge where shit will start to get very real, very fast.

As we arrive at the lodge it is dark, it’s windy, it may be raining a bit. Not sure. We are all tired and anxious to get going. A few of us go over to the lodge to register our car and our intent to be on the mountain for a day. As we start making our way to the trail we get turned around and are already separated from the rest of the crew. A few minutes fumbling back and forth in total darkness we finally get a glimpse of headlamps from the rest of the group and chuckle about how we’re off to such a good start that we can’t stick together in a parking lot. We begin the journey away from the lodge and are quickly absorbed into the forest floor and the night sky.

The first 10km went quickly. The cool morning air was fantastic for running in. The outline of Mt Hood and the surrounding landscape slowly took shape in the early daylight. Our group pace was good. We arrived at our first river crossing. We all took our time plodding the best route to avoid wet feet (something we would care far less about as the day went on.) We continued on and started gaining more elevation as we winded the mountain. We could make out a section of race markers for an ultra that was happening on this part of the trail, though we will be long past it before any racers make their way through.

We remained diligent about our fueling, something that would end up plaguing me for the remainder of the day. I started having trouble getting food down. We continued on. The trail made its way up and skirted along a windy exposed series of snow fields before making its way back into some tree cover. A few more river crossings and switchbacks. We had now tackled 15, 20, 25km and we’re doing good except for not being able to take in much food. I continued to drink water as frequently as I could, assuming dehydration was a factor in my challenges as well. The heat of the day was kicking up as well.

We were now somewhere around 35km into this day and I was not doing well. I struggled to keep pushing as burnout was creeping in. Every uphill just zapped me, but once things leveled off I could run again. Slowly but still running. We soon approached the turn off to the trailhead where we would meet Julia and Annika for our one and only aid station. It was a 2km detour off our main trail, but one that would be crucial to us getting replenished. By this point I was in a bad place. I didn’t want to talk with anyone I wanted to be alone with my misery and work through it. I chugged down a coke, a Gatorade and forced some chips and a sandwich down my throat. I thanked Julia for coming to help and told the boys I was going to keep moving on. I feared staying too long would not fair me well.

I kind of didn’t wait for anyone to respond I just started my way back to the trail and pressed forward. Shortly after, the sugar high of the soda and Gatorade kicked in and I was flying. I hammered out a good 5-6km before any of the guys caught up and could check to see how I was doing. I was feeling golden, but I knew it wouldn’t last. There was a fork coming up in the trail and I agreed to wait there until we were all back together. Spirits were starting to wane by the later afternoon and all we could do is count how many more creek crossings there were, how much more elevation was left. Mathematics was becoming the enemy.

Our choice to run counter clockwise meant we had a big uphill push for the last 10km of the route. Dinner time had come and gone. We had been running for 15 hours now. And by running, I don’t mean running anymore, I mean dejected walking with a hint of soul crush. We saw the sun rise so long ago and it was now setting behind the trees and the late day sky was beginning to pack up shop and call it. We were at 68,69,70km now. This day was taking a bite out of us, and it had sharp teeth. One big ridge lay in front of us and behind it the lodge. THE LODGE! we could now see that we were coming to the end. 1km lay between us and the parking lot we had left so long ago. We were all in pain. Fully spent from the day. But soon shit eating grins took everyone’s face and the adrenaline kicked in one last time. We did it! We arrived at the lodge at about 915pm. In all 18 hours and 73km. This was one for the books.

This has got to be hands down the biggest challenge any of us have ever taken on, and through highs and lows we did it together. We have officially run an ultra marathon. My take away from it is that you have to accept the suck. Embrace the suck. It will hurt, you will feel extreme highs and lows. But it is achievable. I’m extremely proud of these boys and what we were able to do together. The only question that remains is what’s next?

Cheers