I first hiked the Timberline Trail with my friend Bobby way back in 2005. We read about it in one of our many hiking guides and thought “Gee, this sounds amibitious. Let’s give it a go!” We packed way too much stuff, started too early in the season and set off on the trail.
Though we didn’t finish the route, found a parking lot 2 days in and basically did a 39 mile out-and-back, it forever set in my mind as a yearly goal to revisit. Years later in the summer of 2014 my friend Chad and I decided to try it out. He would be driving from eastern Oregon and we’d meet in the middle.
We started late - around 2pm - but hit the trail at a fast clip. This year I went ultra-svelte carrying just 25 lbs of gear. I had either lost or gave away all of my old gear so I had to start anew, opting for higher-priced and lower-weighted gear so my haul was feathelight compared to Chad’s hefty 45 lbs. It made a big difference: in just 3 days we completed the trail, with the last leg covering a staggering 19.5 miles - a feat I’m still proud of.
We tried again in 2016 but due to unforseen family complications we had to cut it short. This year, 2019, we are going to try again. To that end, I thought I would compile a list of helpful links, images and lessons learned from the past years. Here goes!