It’s been a few months since I last posted, lots has happened. I moved to Texas (temporarily!), watched in dismay as a controversial president was elected, did some more traveling and spent time with friends and family.
I think the start of a new year is a good time to reflect on the previous year, which for me was jam-packed with milestones and moments. So–here we go!
The most important milestone of 2016 for me was the decision to leave eHana. After working with my partner Jacob for 15 years, struggling to bootstrap the tiny company of just the two of us in a donated closet-sized office in Kakaako to the shiny eHana HQ with a score of awesome employees in downtown Boston, I was ready for a break. I thought I’d take a few months off to travel and reboot for the next adventure, but it’s ended up being more than a few months!
Some of the many travel adventures from “Sabbatical 2016”:
I feel very blessed to have had the opportunity to travel to so many places and meet with friends and family. For me, getting recharged also involves getting back into nature. In 2016 I had the opportunity to trek into the wilderness:
Looking back at snapshots of the adventures from the year, it’s hard to believe all of the wonderful places I’ve been and the beauty in the world that I’ve seen. I am thankful for the ability and means to travel, and for my wife Lyla putting up with a year of wanderlust and many nights in a sleeping bag.
As I close the book on 2016, this new year’s alarming story has already started being written. I’m motivated to jump back in, later this year. Back to work, being super productive and back to making a dent in the universe. I’ll see you then!
The Timberline Trail is a roughly 40-mile loop around Oregon’s Mount Hood. It’s eye-poppingly scenic, one of few trails I’ve been on that seemed to constantly have fantastic 360-degree views. If you start from the Timberline Lodge and travel clockwise (as most people do), you’ll have Mt. Hood on your right and on the left come a procession of other mountains in the distance–St. Helens, Rainier, Adams, Bachelor and Jefferson. It takes many hikers 3-4 days to traverse, and I highly recommend it–so let’s talk about how to do it!
There are a bunch of sites out there with useful information, and I’ll reference some good ones here. Read these first since they’re informative, but they did leave out some super important information, which I’ll try to fill in.
Oregon Hikers Field Guide – useful for pointing out the campsites with mileage markers. If you buy a map beforehand (or have an offline one on your phone w/ GPS), plot out the campsites you think you might stay at.
The Big Outside – honestly I didn’t read all the words but the pictures were great
As far as mountain hikes go, this has relatively few steep descents and climbs. Any 10 mile section of this trail will be easier than 10 miles of trails like Kalalau, Mauna Loa or Waimanu (Muliwai) in Hawaii, South Kaibab in the Grand Canyon, The Presidential Traverse in New Hampshire, and most Yosemite Valley trails. If you’ve done one of those (for reference), or if you can hike 10 miles a day in the mountains with your pack relatively easily, you can do this loop in 4 days.
Plan your water – there seem to be a ton of streams on the map, but many of the bigger ones are super silty and will clog a filter pretty easily. Don’t feel bad about stopping to fill up and filter water and carrying it when you find a cool & clear stream, since there’s bound to be a campsite you stumble upon that is super nice except there’s no nearby water. If you can, plan campsites & water ahead of time but if you’re lazy like me then you’ll probably just end up begrudgingly hiking after dark until getting to the next water source.
Wake up early – You’ll make it further and have more fun hiking in sunlight. If you dilly-dally around in the morning like we did and don’t get going on the trail until after noon, you’ll end up hiking in the dark which is not as much fun.
Make a fire – most established campsites will have a fire ring for you to safely build a fire. There’s tons of dead, dry wood around most of the campsites and it’s a nice way to stay warm, so bring some firestarting tinder (or your best bushcraft) and some campfire stories to tell.
There will be berries – If you’re hiking in mid- to late-summer the berries will be ripe! Huckleberries look like blueberries but are not. We called them not-blueberries and they were plentiful on the trail and tasty although a bit tart. You’ll also probably see yummy raspberries, and another red berry (mountain ash berries?) are abundant however unfortunately don’t taste very good.
Map – we all had smartphones with maps, but Google Maps is not detailed enough and you’ll probably lose signal before you have the presence of mind to download an offline map. You can buy a map for $12 from the gift shop of the ski lodge (the dull concrete building across from the more ornate Timberline Lodge)
Gaiters – probably the number one thing I wish I’d packed but didn’t, I only saw a few other hikers on the trail with these and was super jealous. There is a ton of dust on parts of the trail (perhaps because of the recent fires), and in a few sections you’ll be scrambling through loose gravel and rock, which will keep getting into your shoes. So do yourself a favor and bring these.
Hiking Poles – if not two, bring at least one. They are super useful for stream crossings (which you’ll be doing a lot of). The water level was low when we went in August, so we were able to avoid getting our feet wet in all but one of the stream crossings by gingerly making our way from rock to rock (and leaning on our hiking poles liberally to ensure we didn’t slip).
Sunscreen, sunglasses & hat – there’s an exposed section of trail after the Eliot crossing that’ll cook you if it’s sunny out. You’ll probably have a long-sleeved shirt since it’s pretty cold at night (even in August), so bring one that’s light enough to wear during the day to protect your skin.
First Aid Kit – sounds obvious, but you probably don’t have cat-like reflexes like me and you’ll slip at some point on either the loose rock or the slippery ones when crossing a stream and you’ll cut yourself, I guarantee it. Luckily due to my cat-like reflexes I didn’t.1
Don’t buy “Around & About Mount Hood” – You’ll see it online if you’re researching the trail, I bought it in REI in Portland, it’s probably in the gift shop at the lodge. Mostly contains info about accessing different parts of the Timberline Trail from various parking lots which you don’t really need if you’re doing it as a loop. We bought two copies which regrettably didn’t get much use.
Paradise Loop – Don’t skip it! You’ll get some nice pictures and it’s also a great place to camp (although pretty close to the start at only a little over 5 miles from the start).
Eden Park – Don’t skip it! It does add a little bit of elevation gain but you’ll also get a scenic meadow and a walk through some crazy silver-white and heat-curled dead trees, a reminder of the recent fire. It’s probably super creepy at night.
Eliot Creek Crossing – The trail for this section is not on the map, but don’t worry too much about this, as of August 2016 the trail is pretty clear right up until the ridge before the creek, and after that the markers aren’t great but the false trails are obvious because they simply vanish into thin air and drop a few hundred feet. Then just go back up the trail and try the next one. Probably the most annoying thing about this section is the loose crumbly rock and gravel, but you remembered your gaiters, right? If it’s been rainy and the stream looks swelled and crazy don’t do it, but otherwise just take it slow, be cautious and you’ll be fine.2
The Last 2 Miles – this isn’t really a recommendation since there’s no way around it but the White River Crossing and then the steepest climb of the loop are your reward for doing the Timberline Trail clockwise. The last mile of uphill through quicksand-like dirt left me thinking “I can’t think of a worse way to end a hike than this”, but then a quarter mile before you get back to the parking lot the sand stops and you forget all about it as the Lodge comes back into view. Just know that this part is going to be bad for 2 miles, and then hopefully you get back to the parking lot in time to have a nice meal at the Lodge.
If you’re thinking about doing it, do it!
We did it as a last minute, poorly planned adventure, so mainly got on the trail way after noon every day and ended up hiking into the night, searching for water. And then on the last day I had to hike 15 miles to get out due to poor time/mileage planning. But you won’t do that because of all the tips I gave you! Even though we didn’t plan very well we all still had a great time and the weather was stupendous, sunny yet mostly cool, visibility for miles and not much wind. I highly recommend the time of year we went (late August). The pictures don’t do it justice, and it was one of the best backpacking trips I’ve gone on so far. I hope this helps you plan your trip if you decide to go, and if you do, let me know how it went!