In this adventure I’m up at Timberline Lodge with my hiking partner Don, and we knock out the Timberline Loop (Timberline Trail) all the way around Mt. Hood in Oregon. We start by filling out the wilderness permit, tighten up the shoes, and get after it. The loop is packed with classic Hood scenery—creeks to filter from, big open views, wildflowers, and plenty of exposed sections where the sun just bakes you. We break it up over multiple days, with a solid first push of about 17 miles and roughly 5,000 feet of gain, and I was definitely feeling it rolling into camp late. The big takeaways on this one are the river and creek crossings—some of them are straight-up sketchy. We cross stuff like the Sandy River, Eliot Creek, and the White Salmon basin crossings, and there were moments where I was thinking, “I don’t want to have to do that again,” but we got through it. Cloud Cap was a highlight for me too—those old rustic lodges with the boulder foundation look like a castle from across the ridge, and the Mt. Hood views up there are pretty darn sweet. We finish with an early morning push back to Timberline Lodge, a little rain to send us off, and then it’s back to the car to wrap the loop.