Timberline Trail – one night one push, failed attempt at double!

Ever since the Wonderland Trail I have been obsessed with the idea of double circumnavigations. Ras Vaughn has done a double Wonderland (maybe the only person to do so?) and as we got back to our car, I felt a deep sadness. I would have traded a lot to have been able to turn around and go again! In Ras’s blog he ends a one loop trip around Rainier with this:

“Can you imagine turning around now and starting all over?” I know he meant it as hyperbole. I know he intended the question to be so ridiculous as to be rhetorical. But in my mind I answered, “Yes, I can. I can indeed.”

I felt the same way after Wonderland. I don’t have enough time this summer to hit the double Rainier circumnavigation (I estimate it would take me 5 days) so I started plotting on my home mountain, Hood. Hood has been the scene of much happiness, much madness. The loop trail, the Timberline Trail, is 40 miles. Last time I tried to hike it in one go I only took nutella, and ended my day after a really challenging creek crossing crying and puking. I camped next to new friends Taylor and Pierce and it turned my day around amazingly, but I have wanted to do this trail in one push for a long time. What better way to do this than try to do the trail TWICE in one push? My new running friend Paul said he wanted to do it twice in one weekend, separated by SLEEP. I did not want to do this and made plans to hit the mountain this weekend!

I estimated the full 80 miles would take me 30 hours, hopefully faster. After discussing the idea with Jeff (who has set endless FKTs this year and is one of my total running inspirations – I hope to run with him soon!) I decided it would make sense to hit the night loop first. I love to run in the dark, but I mentally really struggle with a full night. I have never done a full night solo. I often get up at 2am and run, but whenever it gets dark in the evening I mentally feel like my energy drains with the sun. I get scared (sometimes rightly so), I bail. Only once on the PCT did we have the idea to literally hike through the night, on Hat Creek Rim. I got all jazzed up for it but Scrappy and Short Shorts bailed. I thought for about 2 minutes about continuing into the night by myself, but felt self-induced pack mentality so stayed with them. I think back to this moment often. I hiked in the dark all the time on the PCT and was never afraid of anything, so what was this intangible difference? This goal would involve a full night by myself, where I would NOT be able to bail. Eek. I know this fear is silly – I am totally happy camping by myself, so what should the difference be? If anything moving and being aware is safer than turning yourself into a slumbering burrito? I accept there are some routes that aren’t sensible to run solo at night – Issy Alps may be one of them – but Timberline Trail is remote enough that you’ll only see hikers. Much less likely to bump into dangerous people.

Strava tracks
As I have bitched about incessantly, time off in America is hard to come by. I have very forgiving bosses and coworkers but I was only able to leave work at 1pm. With traffic and multiple work calls, I didn’t arrive at Timberline Lodge until 7.15pm. Ah! It was rainy and cloudy but dang I love Mount Hood. It feels like home and although I love Seattle dearly (and am learning to love Rainier) I wish I were that bit closer to Hood. I was so happy to be there! I changed into my dress even though it was cold and windy. I bumped into two guys in the parking lot who were clearly heading out on trail. I asked about their plans but they just looked at me oddly. I guess a pretty dress and running vest makes for a confusing picture!
I was running by 7.30pm which was a very fast turnaround, but way later than I had hoped. 5pm starting would mean I would have quite a few miles under my belt by the time it got dark, and when I began it was already dusky. I ran through the PCT camp section and they were all already in bed! My legs felt BRILLIANT despite having raced only 6 days before. As I began the mountain came out! I was thrilled and so happy!
The sandy downhill was a lot of fun and I quickly bumped into Eloise. We worked together at Powells (big bookstore in Portland) in 2016 when I was temping there. It was SO GREAT to see her. She’s a major mountain crusher and I’ve been following her from afar since, always inspired by her real talk and commitment to trails. We snapped a quick selfie and although it was tempting to stop to talk for hours I had to keep moving while there was still some light.
Already looking haggard, zero miles!




First several miles very easy. Occasionally got lost in the sand but nothing major. Clark Creek (I may get all of the names wrong…I wasn’t looking at a map for most of this trip so it’s just guesswork trying to patch it together) was my first vaguely serious crossing of the day. River crossings are always ominous to me after a tough year in the Sierra in 2016, and I had a tough time on the Timberline in 2017 too. This was mostly allowing myself to feel the fear, rather than them actually being scary. However Clark Creek was totally easy – I believe there was even a log! I already had wet feet and generally don’t trust logs but I walked through the river and used the log as a handrail. Lovely.

Perfect pink mountain

I passed many tents and saw a lot of people just getting ready to go to bed. People were generally very friendly, although I will say that only one group asked the right questions. In my not so humble opinion, you can always check the person’s destination, check they have the right equipment, ask if they need anything and if they’re feeling good – then done. One group was super great and cheered me on, but almost everyone else was pretty negative, and didn’t ask any safety questions. I’m always down for people to check on safety, but just looking at my disbelievingly and calling me stupid or saying I won’t be able to do it isn’t helping anyone. I don’t criticize how you choose to experience the mountain, don’t criticize me. I moved quickly and tried to stop talking to people so much. Oh I would wish for people to talk to in a few hours! The sky was growing properly dark as I pulled out of Mt Hood Meadows proper, and I began to wonder how many hours of true darkness I would have. I knew the sun technically set at 8.30, and technically rose at 5.30am, giving me 9 hours of darkness, but how dark would it actually be? My question was answered at 9pm when it did became dark enough for a headlamp. Hmmm. Eight hours of true darkness felt like more than I really could handle, but my countdown began. Eight hours, and 1.5 hours had already passed in a flyby. Eight would fly by too?

I pulled through another campsite that I remembered by Newton Creek. There were lots of tents and people milling around. I stopped and walked through so as not to disturb anyone. Lots of people were in fact disturbed and stopped talking and stared at me. ‘Hi guys!’ I said, as I couldn’t really see them through the glare of their lamps, and the river was too loud for me to hear. I gave them a thumbs up and moved on. However as I made my way down to the river they started to really freak out. I couldn’t hear anything over the roar but they all came down to the banks/side of the river to watch, and were signaling lots of unintelligible things with their headlamps (presumably the flashing lights meant NO! Don’t do this!). I wasn’t going to go back up to tell them that I was perfectly OK. It did feel like a lot of pressure particularly as this crossing was a full and fast body of water, and it was too dark for me to really see where I was going. I wasn’t going to let the pressure of many headlamps staring freak me out, so I took my time assessing, and quickly found a log. Admittedly I had to crawl over it, but a log crossing nonetheless. It was then a challenge to find the trail on the other side, but I made it! I was extremely glad to pull over the ridge away from their scrutiny. I’m sure they were completely well meaning and it was kind of them to watch me cross but without being able to hear or see them it stressed me out.

Gnarl Ridge. 8 hours left until light. This was a wide open section of really volcanic trail and it was just amazing. The clouds had blown away and the stars brimmed over. There was only the occasional light breeze, and it was extremely peaceful. I’ve never seen so many shooting stars, and even the non-shooting stars were shining particularly brightly. The sky was this starstuded darkness, this glittery world wrapping around me until the ground underneath my feet. I felt completely at one with 360 degrees of my surroundings. I couldn’t see them properly but I could feel it. My world felt huge, I felt grounded within it. The sky was only interrupted by the ominous darkness of the mountain. My world was both reduced to the two feet illuminated by my headlamp and also the entire world of the sky, the stars, the mountain! This night was not going to defeat me.

What most of my night looked like


Cloud Cap. 6 hours left until light. I didn’t even need to really repeat this mantra too much. Life was fantastic. I kept feeling the beginning of fear in my stomach – any rustle behind me, any slight trip on the trail. ‘Fear tastes like a rusty knife, and do not let her into your house’. Some things about the night ARE scary, but I was in control and not letting panic control me. I could see many tents and heard the comforting sound of car engines. I can bail here, I said, but I don’t need to. I don’t need to stop. This evening is yours and you are enjoying every minute of it.


Imagine thousands of bright stars above, then you have the scene


I think it was Eliot crossing (and I think this was after Cloud Cap? hard to remember now!) that was extremely challenging. The river was harder, thigh high, but OK, but finding the trail afterwards was impossible. I went left and right, each time concluding that this was definitely wong because it just became a cliff, and then trying the other direction and concluding the same. Eventually I stopped for a minute, tried to force down a bar, spat it out, continued on. I had seen a tent on the top so I knew they had made it and there was a trail! There are heaps of cairns marking river crossings but in the dark I couldn’t use them effectively. I eventually found it and was thrilled.

My only problem was that I felt extremely sick. Maybe downing multiple cold brew coffees just before setting off was a bad idea. I had managed 1 bar, and I had a backpack stuffed with 3000 calories of tried and tested favorites, but absolutely nothing was sticking. I forced myself to nibble on a cereal bar but even 5 hours in (by which time I should have eaten 1000 cals) I couldn’t choke down more than a single mouthful of bar. Pretzels, gummies, ginger, polos, plain bread – nothing! I eventually stopped really trying to make myself eat reasoning that the cool darkness meant I would be able to get by on less? My running logic is…dubious. I also invented the concept of ‘silly math’ with how I was counting down time until the sun came up. Realistically it was 6 hours at this point, but that seemed far too far away, so I was practicing silly math – which is essentially saying it’s only 3 hours, then laughing maniacally. This joke doesn’t translate so well to paper, but I was laughing OUT LOUD at the concept of silly math for many hours. This sweet trail mania is one of the reasons running is so dear to my heart. The world gets weird in a certain state of exhaustion, and although I can hit it hiking, running gets me there much faster. Everything takes on a more vivid hue, and even my bad jokes become funny!

I was in and out of the trees. It didn’t take long for my hearing to fill in much of my missing senses. I could hear river crossings coming from miles away, but it is amazing how the water can be SO loud, but cross one ridgeline and the sound disappears entirely. I enjoyed switchbacking down to the water and hearing how different it sounded from different points. On one I could hear the waterfall, then how it got more gentle afterwards. Luckily there was a log, so easy to cross. On I went. The crossings were challenging in the dark, just trying to scout them out to find the best place.

This was pitch black but I used my headlamp to illuminate the shot.


I now cannot remember exactly where I was, somewhere just before Elk Cove I believe, around 2am in the morning. I had put on a podcast before but turned it off as I was enjoying the peace and quiet – I literally hadn’t heard a thing as it was such a still night and there were zero animals out and no other people. I was pulling up a slight incline. All night I had been seeing twinkling stars, the occasional red lights of satellites. Suddenly in the darkness I could see two bright green lights, unmistakable eyes, then a rustle. My heart actually stopped, and I moved so I was facing the eyes. It moved over…four eyes. Two cougars. I was unable to move for who knows how many seconds, then fumbled for my phone, trying to get a loud podcast to play. I couldn’t muster any words (I have a recurring nightmare where I’m being chased and am unable to scream and it seems like this might have merit!) but managed to get Car Talk playing loudly. It was quite surreal standing off against these two terrifying animals and having Click and Clack’s ridiculous laughs reverberating through the trail. It did not scare them away. I lifted my hands above my head and mustered words. ‘HELLO CATS. YOU AREN’T GOING TO GET ME TODAY. I AM JUST PASSING THROUGH!’. They were standing in what looked like a pretty established campsite, although there were no tents nearby, and I was definitely getting a territorial vibe, like I had rudely interrupted them, which I suppose I had. I remember thinking that I definitely wasn’t going to be able to strangle two lions, and in fact I probably couldn’t even strangle one with my willful negligence of upper body strength. I know you’re meant to throw stones at them and be aggressive, but why would I pick a fight with two cougars? They hadn’t moved a muscle since the first one had moved to be with its friend. (I have subsequently been told cougars are solitary animals so it was likely a mama and baby). I also did not want to bend down to pick up a stone as this would make me vulnerable. Nothing happened. I talked again, nothing. I turned Car Talk off, all the time keeping my headlight bright on those four green lights. Nothing. I started to move down the trail, and they moved with me. Slowly, for sure, but moved with me. They kept that 10 meter distance very consistently. I wish I could say I got used to having them follow me, but I did not. I was side stepping slowly down the trail so that I didn’t turn my back to them, but also I knew I must not fall. They followed me very diligently through Dollar lake until I started descending towards the river. They didn’t follow me to the water, but stayed watching me. I almost felt comfortable running. I forded the river illuminated by four eyes, and as I started heading up the hill on the other side I saw them still staring. It was an extremely territorial encounter, and in hindsight I am beyond thrilled. I have never seen any wildlife on trail before (still have yet to see a bear!) and although this was an extreme induction to animal encounters it was a real shot of all sorts of adrenaline. I pushed on until another river crossing (? honestly a bit blurry where I am – somewhere before Cairn basin), which I forded, then collapsed in a heap for a minute or two. I was exhausted and needed to eat. I managed half of an english muffin (my boss has been eating them for breakfast and inspired me…I thought longingly of the safety of my office…still would rather be right here on this trail than there – although I love my job the lows and the highs just aren’t as strong!). I then tried a 5 hour energy which I instantly spat up like a baby. Oh well. On I went. I began a pretty steep descent and thought ‘hmmmm I don’t remember this being here’. I only went for about five minutes when I checked my GPS and realized I was totally off course. My GPS tracks show this to be at Cairn Basin. Oops! Not too big of a deal though as I found the trail junction without difficulty. Then, not sure exactly what happened, but I think I should have turned left, and turned right…but one way or another I went the wrong way. I was traveling counter clockwise, and suddenly reversed and started going clockwise, back in the direction I had just come from. I think I was on heightened state of panic due to cougar situation si wasn’t thinking sensible. 

At this point I was completely unaware of my mistake. I climbed back up the hill I had just descended, then descended back to the river and crossed it again. I think it speaks volumes about how little I could really see of my surroundings that I went back almost an extra three miles and truly had no idea. This wasn’t to say that it wasn’t beautiful, because it truly was. Seeing the charred and scorched Dollar burn area in the glimmer of starlight was breathtaking. I was seeing the world in miniature detail so sort of lost that large scale understanding of…direction. Or at least this is what I’m telling myself. It becomes more inexcusable when I checked my GPS after the river crossing (on which I fell on the exact same rock as the first time), it told me I was going the wrong direction and I thought ‘weird it’s not working properly’, put it away, and continued on. I think exhaustion was making the decisions at this point!
After a few miles I realized that the mountain should always be on my left, and it had in fact been on my right for quite a long time. Oops. It was a bit painful to turn around particularly as I now felt TOTALLY confused about what direction I was going and where I was, and turning around would be admitting I had just done some of the slowest bonus miles known to man, but in some ways I felt quite cheerful. There was no stopping to have a sleep or a temper tantrum as I didn’t want to bother anymore territorial cougars, so back I turned again! Crossing this same river three times was totally ridiculous but I honestly wasn’t so bothered. I now knew I was back on track, and it was time to work harder on eating something. I choked down half a coconut bar. I then saw literally the brightest and longest shooting star of my life, bright orange with a tail of fire. Was this legit a comet? If I hadn’t gotten confused, I wouldn’t have seen this. I’m with Blair Waldorf, destiny is for losers, but at this point I truly felt like everything happens for a reason, and that this strange night on the mountain had been custom made for me.
I started to really blast podcasts loudly through this whole area. There were very few people in tents. I wasn’t even listening to them but My Dad Wrote a Porno was loud enough that I thought the cougars would be well warned of my presence. Car Talk clearly wasn’t scary enough for them, but Rocky Flintstone apparently was! It was still so dark but this section of trail was a lot easier. Super flat, but just enough trees to keep me on my toes.
Eventually my phone rolled onto an interview of David Roche by Candice Burt. David Roche is part of the duo who advocate for happy running – honestly, I found his and Megan’s book completely unrelatable. He’s one of the best coaches at the moment and always seems extremely accepting and nice. In this section he was talking about how yes, running crazy distances can be good, but we need to do it for the right reasons. If we think a finish line is going to solve our problems, we are wrong. He talks about how runners need to identify the compulsion driving them to run, and isolate that away – be that compulsion self judgment, loathing, impatience. It doesn’t matter. We run because it enriches our lives. They were talking about extreme running, and in my final hour of darkness David Roche said something like: ‘You have nothing to prove. You’re awesome and perfect the way you are!’
At that point I let out a major sigh of relief. My relationship with running has been changing (a post for another day) and these words confirmed the direction I have been going in. Yes, this was going to technically be a failure of a mission, but that was OK. Even in the 8 hours I had been out I had crammed in a lot of adventure. I can’t wait to be in a place in my life where I have more time for unequivocal sufferfests, I wanted to do the double…but I also wanted to WANT to do it, if that made sense. Pushing is fine, type 2 is fine, discomfort is fine…but with all my major accomplishments, I’ve ultimately been happy and found meaning in them. The double Timberline is going to be an awesome route for a wonderful day, but I hadn’t done the necessary prep or given the challenge adequate room. I was OK with that. I know this has been a summer of failures, but…doing a David Roche and relooking at this…it means I have tried some really awesome and cool things with limited time, and had many successes along the way!
My cougar experience had blown through quite a few hours of my night, even thought the minutes had been years long, my miles had also slowed down considerably. I only hit the wooded descent to Bald Mountain at 5am, well behind schedule. Oops! Again, in the new theme of my running, I accepted the unchangeable facts…I’m reading a lot about how time is a purely human construct, but I too am just human so am subject to its reality!
I had been desperately waiting through the hours for a glimmer of morning, that had been long delayed in coming. I was delusional in thinking the world begins to get lighter at 2am. I felt like I was closer to seeing an orange sliver of the Friday sun than any reality of Saturday morning. Finally as I pulled through Bald Mountain Hood illuminated pink, and my headlamp was away. I could have wept. I had made it through the night! I have never done this before and I’m not sure when I’ll do it again, but I’ve done what earlier this year I concluded I could not!


I was still starving, still nauseous, and just didn’t want to stop as I was SO FAR AWAY from Timberline Lodge. Probably a good 12 miles to go which doesn’t sound like much, but I had accumulated a major calorie deficit at this point and had no intention of eating anything, so the problem was pretty much sticking around. I was also tired, BEYOND tired. I ran White River 50 miler the weekend before, didn’t recover properly from that, had a standard crazy week at work, went out and SOCIALIZED during the week (shocking!) so was pretty tired even before starting this challengine. A full night without sleep had tipped me over the edge into full mania. I began to hallucinate other hikers. I have never done this before and it was a weird experience. I would see very vivid outlines of people – a man with a green backpack kept reappearing. I sort of understood he wasn’t real, but nonetheless I sped up to try to catch him. I stopped and tried to sleep for a minute right on the trail as I couldn’t seep my eyes open. This Courtney Dauwalter 1 minute style nap was interrupted by some honestly pretty rude ladies. I had heard them coming and rolled out of their way but they looked at me like I was pure filth. Yes I was lying in the dirt in a pretty dress, yes my eyes were bloodshot, yes I didn’t have a proper backpack like they did, but goddamit you can still be polite!

Trail nap scene

I just got up and kept moving. It was a pretty busy section of trail back to Timberline and I got some very weird looks and comments. You see trail runners doing the whole Timberline Trail in one day (nobody thought this was me!), backpackers doing it in 4 days, PCT thru hikers sharing a few miles of trail before they head to Canada, then tourists out from the lodge for a few miles. I stopped and talked to every thru hiker I saw. They were all wonderful and I was very envious of them!

Some of the trail runners were pretty rude, some were awesome. One man really gave me a stern talking to when he asked what I had been doing. I said ‘I just ran the whole Timberline Trail’ and he said ‘no, don’t say that, the Timberline Trail is the loop that goes round the whole mountain, you shouldn’t say you did that if you only did a few miles, people will get cross’. I said ‘no, I understand what it is, I’m saying I did it!’. His confusion at first was fair enough as I was wearing a nice dress and wearing a tiny backpack and it was 7am, but I explained patiently many times what I had done and he insisted I was just not understanding what the Timberline Trail was…thanks mate. On I went! Plenty of very nice people, and I bumped into the people from the parking lot the night before. They were friendly but also seemed confused. Another person asked me if I was a wedding guest who had gone for a short hike in the morning and gotten lost! If I showed up looking like that to a wedding I don’t think I would be let in!

A hot mess
The miles were long and hard, and it was hot. I had thought I would be back at the car before the sun so I had no hat, sunscreen or sunglasses, and I was frying. I was in a salt deficit so it was just a slog but I eventually made it, still able to run a fair amount (but also taking 40 minute talk breaks to chat to PCTers…oops!)

I collapsed back in the lodge. I slept for a fitful hour and managed to slurp a diet coke. Wow! I knew I wasn’t going to head back out for loop 2 but I still didn’t want to leave the mountain. The double loop is a worthy adventure for a worthy weekend and I can’t wait to come back. This is the first time I’ve bailed on an adventure and been unequivocally pleased, able to focus on the highlights and accomplishment along the way…maybe going easy on myself is working?!


Nutrition! Something has gone wrong with me these few months and now I feel sick after running 10 miles, pretty consistently. What is this? I had packed a really good variety of foods as well as some true staples and nothing worked.

Sleep: I am super proud of myself for doing a true zero sleep adventure. It is nonetheless painful to admit I probably would have gone a lot faster, found it more fun, and potentially even achieved my 80 mile goal, if I had slept. I have a really sweet bivy setup, and I would be happy with even 1-2 hours. It was warm enough that if I hadn’t bumped into the lions I probably would have slept.

Weekend warrior-ing: I LOVE being a weekend warrior. I try to make the best use of my 5pm Friday-late Sunday as I possibly can. I thought this 80 miles was a weekend sized adventure. I was close, but no cigar. It was a 3 day adventure. It only needed 30 hours of trail time, but the drive down from Seattle/drive back + preparation pushed me over the 40 hours I actually had. Everything just felt rushed – I got to Timberline at 7.20pm and was on trail at 7.30. Not enough wiggle room. Oregonians would be able to hit this easily in just a weekend – for me, not feasible!

Timing wise: I think my plan to do the night loop first was wise, although navigation sure would have been easier if I was more familiar with the trail from the day! I got a 7.30pm start. I think if I could have started any time between 2-4pm on Friday it would have been perfect. I was so slow on the first loop with cougar gate and getting lost that I for sure would have finished up Loop 2 at about 1am which I wasn’t keen for.

Animals: Considering a slingshot.


1 thought on “Timberline Trail – one night one push, failed attempt at double!

  1. Love that trail but never experienced it like that before. Great story. Thank you.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this:
search previous next tag category expand menu location phone mail time cart zoom edit close