Wy’East by bicycle with the bitty bro!

A million years ago, my brother and I talked in the abstract about biking to Mt. Hood (to be all settler-name about it) and climbing it. The conversation went something along the lines of why haven’t you climbed Mt. Hood yet when you live so close to it? (him) and I’m not sure I care that much to bike there with all my mountaineering shit and lack of actual mountain-climbing confidence and then climb it (me). But we sort of landed on — again, a million years ago, in the abstract — that if I could drag him out there on a bike, he could drag me up the mountain to the summit, and we could probably do it in under 24 hours.

So, this past weekend we did it!

My brother and sister-in-law and sweet little niece were in Portland for a few days, and we very last-minutely decided hey, why not?


(just two biking goobers trying not to freeze in the very early morning)


I will say, this is where having a little brother who is actually a skillful athlete is helpful, because I definitely did not feel like climbing Mt. Hood was something that I would ever do on my own off the couch. Mostly because even though I know it’s a (relatively) accessible mountain to climb (as far as glaciated peaks go), I also know that people slide off it to their deaths every year, and I also know that I am not (yet!) a very confident snow or glacier traveler, nor yet a good interpreter of snow conditions. But Alex was pretty confident it would be fine, and I definitely trust that fool to know a thing or two about mountains and also not lead me to my death.

The biking, on the other hand, I felt supremely capable of doing, even if my bike weighed 80 pounds (okay, slight exaggeration;) more than Alex’s;)

So! We woke up at 4am on Saturday all bleary-eyed after staying up too late hanging out on Friday, and were biking by 4:30. It was already light out and we had a glorious ride along the Springwater path out to Gresham, complete with a plethora of rabbits, two coyotes, a deer that I thought was a large beaver from a distance until it moved, and a symphony of singing morning birds. We got on Highway 26 at Stone Road, a little shy of Boring, and were kind of surprised by how many people were already driving east by 5:30am. But despite the loudness of cars it was actually a fairly pleasant ride.

Ha, actually, it was a really, really cold ride. I think we were both surprised by how frozen we were starting out (and by how much we went downhill before we actually finally climbed the 8,000 or whatever it was cumulative feet to get to Timberline Lodge). But looking back on it now, it was a fully pleasant ride:) Especially once we warmed up a bit.


(woohoo the last part before we got to Timberline Logde! We’re headed for the top of that thing!:)


When we got to Timberline, about 56 miles and 6 hours after we left my house, we met up with James, Sanni, and our sweet little niece who had all driven out to meet us and bring us snacks and our climbing stuff. This was an adventure right in the middle of a family visit, after all, and it was much nicer for this to feel like we had family touchpoints along the way rather than Alex and I just questing out and being gone the whole day by ourselves. So we had a sweet little 10:30am picnic, which to Alex and me felt very lunchlike at that point but then I realized it was only 10:30 and it was… breakfast 2? Breakfast 3? At any rate, it was more calories of real food in the middle of the adventure, with our family. Big thanks to our support team here:)


(the sweetest support team! Picture by Sanni:)


After a quick costume change, some baby snuggles, partner smooches, and a little bit of a hike up all together, Alex and I started up the mountain for realz around 11 while Sanni, James, and little June took a stroll and played in (/ate) the snow (awwwww).


(here we goooooo!!:) picture by James)


So, something I was nervous about was the fact that I know most people climb this mountain super early in the morning, I presume in part because it’s less slushy and your crampons bite into things better. So I was nervous that we weren’t starting until 11am, when the sun was rather brutal and the snow was turning to smoosh. I was also nervous that from Timberline, it looks very, very steep (did I mention that icy things that you can slide down make me nervous, even if theoretically I know how to use an ice axe and also have done such things at least a little bit before?). I was also nervous that this feels very late in the season to climb Mt. Hood, and who knows what matter of rocks and things were just waiting to melt out and fall on our heads, especially late in the day. But again, this is where it’s helpful to go with someone who is supremely confident about such things, because that rubs off and makes me feel like, hey, sure, no problem, I got this too.

And it was fine! Despite talking up how Alex was gonna have to carry me and how I’d be too scared, it never actually felt that scary, and we made it to the top in about 4 hours. We joked the whole time that we were the late-shift climbers, since on our way up we met every single climber already well on their way down already (those who hadn’t gotten down before we even started, that is), and by the time we got to the last steep push before the summit, we were the only ones that high on the mountain. Which was pretty neat, since we got the whole summit to ourselves on a totally beautiful day with all the other mountains out:)


(no one else there! picture by Alex)


(just two siblings on top of a mountain!:)


And then to get down it took us only an hour and 15 minutes to undo all the climbing that it took us 4 hours to do, ha. Despite the fact that I am the most hopeless and awkward of boot-skiers, which scandalized little Bitty Honnold to no end. So, we made it happily back to Timberline, a little under 12 hours after we’d left my house in the morning.


(Alex on the way down. It was so fricken delightful! Look at how lovely this all is!:)


(and this too!! Once we got high enough, DAMN it was so fricken cool!!)


We decided to drive home with the team rather than bike home (did I mention this was a family visit?;) so that we could hang out all together in the van and eat dinner together before little June went to bed — which I think was the right decision even though it would have been elegant to bike home too. And thus much food was cooked and jointly consumed on our back porch, and all was well.

So, moral of the story: I dragged Alex to a mountain on our bicycles, and he dragged me up the mountain in our boots. Excellent sibling synergy like we do, with some clutch support from the partners-and-niece team. I’m psyched to have climbed my backyard volcano now AND that it wasn’t even a whole big thing! And a self-supported ride/climb/ride home in 24 hours definitely feels like it would have been possible, even with carrying all our boots and stuff, given that we had 12 hours still to play with and the ride home would have been much faster than the ride up.

And thanks again to our family support team for being so gracious about hanging out at Timberline for like 6 hours while we got there and climbed a mountain <3 Truly the best:)


  1. Man, just thinking about doing 56 miles in six hours with 8,000 feet of climbing and starting before dawn is too much for my brain to handle! ;-) Congratulations.

    But I just want to address this:

    “A million years ago, my brother and I talked in the abstract about biking to Mt. Hood (to be all settler-name about it) and climbing it.”

    Well, I am all with you on dogging on settler names for landmarks, but there is now evidence that Wy’east is probably a made up name by a white person as well that sounds native enough to trick us:

    Unfortunately it seems like the native name for Hood has been lost to time, though other mountain’s traditional names, like Luuwit for St. Helens, are correct.

    The worst has to be Lake Itasca for the source of the Mississippi. It’s a fabricated name made by a schoolteacher out of two Latin words, veritas caput, or “true head” (of the Mississippi.) But it “sounds” native, which was his point. But we do know the Ojibwe name for it: Omashkoozo-zaaga’igan, meaning Elk Lake.

    • hey there! Yeah, I hear you on this, and I’ve read some articles about Wy’East potentially being made up BUT I still think it’s a good thing to remember that we don’t just have to call it Mt. Hood and that there ARE and have been other names for it. Which is why I persist in at least using an alternate, even if that alternate is also problematic.

      Not sure if that’s the right way to go about it, but that’s where I’ve landed currently.

  2. Oh how I LOVE this story and the engaging and fun way you told it! Forget about biking and climbing (haha) seems like there’s another writer in the house!!

  3. With you two standing next to each other the family resemblance is hard to miss. I’m hoping to bag either South Sister or Adams this year. Still haven’t done Hood either. Thanks for the inspiration.

    • oooooh, yay! Have you climbed Mount St. Helens? I feel like in order of difficultly, maybe it’s Helens < South Sister < Adams < Hood. I didn't know you were into mountains, other than biking over them;)

      • The “big” mountains are new to me. Back in NH we have 48 peaks all over 4,000′ but Mt Washington is the tallest at 6,288 (and “worlds worst weather”). So yeah I need to get some of these taller peaks. I have not done St. Helens either, that too is a goal, but I think the idea of Adams appeals to me more at this point. I’m just fascinated by South Sister too. That whole area is probably my favorite spot in all of Oregon between the city of Sisters and the cascade lakes.

        The order in which I prefer to do things is bike, hike, run (a distant 3rd).

  4. Sherry Trechter

    How fantastic! Thanks for sharing your ongoing adventures, especially for an old lady in assisted living propelling herself in a wheelchair ♿️

    • Oh my gosh!! SHERRY!!! Holy shmoly! Thanks for “stopping by” here and saying hello!:) I’m always into the vicarious adventure, either providing to others or partaking of myself — we’ve all got adventures to share, after all:)

  5. What a great story and what a great brother sister pair. Made my heart clinch as I miss my own beloved brother so so much. Never lose these memories.

  6. Wow what an adventure! This makes Ainsworth Hike/Bike Camping from Portland seem like a walk in the park. Nice meeting you. Jeff.

    • Whaaaaaa? Ha, how did you even find me? But, YAY! This makes it much easier for me to find your youtube channel;) Nice to meet you too! (And I hope your ride back was great:)

      • You have a unique first name that stuck in my head and are such a positive ambassador for Portland and Car Free life I googled. Have a great summer!!

Leave a Reply

Your email address will not be published.