With a clear weather forecast and some free time in the last week of September, I took three days and beginning from Timberline Lodge, walked the approximately 40 miles of the Timberline Trail around Mount Hood.
Deciding to leave From Timberline Lodge, gave me an opportunity to have a nice dinner and then about a mile and sleep at a small campsite at the edge of the ski slopes. Packing light, I used my MSR Elixir tent, Mont Bell 30 degree 800 fill down bag and 4 days of food. I used an MSR stove, carried 2 16 oz fuel canisters, a small stainless steel pot, a cup, bowl and a 1 litre water bottle. I used an Exped 40L alpine guiding climbing pack and carried Arctyrex rain-gear, OR soft-shell and hiking trousers, lightweight hoody, 2 Synthetic T-Shirts, 2 pairs of running socks, Salomon XT running shoes, running hat, brooks running shorts, sunglasses, headlamp, 2 notebooks, a map, Suunto MC1 compass, a knife, a small aid kit with wire, small pliers, screwdriver, dental-floss (for sewing) needle, some duct-tape, ibuprofen, tweezers, eye drops, lip-cream, 2 lighters, fire-starting kit, 50 metres of parachute-cord and a Samsung S7 smartphone. The pack and phone are waterproof, so I used only one stuff-sack for sleeping bag. The pack weighed 32 lbs. Items I did not take but wish I had taken: A hiking pole and additional water bottle.
Not any small section of this trail was unspectacular. On day one, going clockwise, I walked through dense forests, filled with douglas fir, mountain hemlock, hawberry, huckleberry and blueberry bushes. The trail climbed to alpine desert ridges, crossed stunning alpine meadows with flowers, grasses and heathers. It descended beside and into deep canyons and crossed numerous small creeks as well as three challenging rivers: Zig Zag, Sandy and Muddy Creek. The last was difficult.
A quick side note on rivers. They are the more hazardous element of this circumnavigation hike. My decision to make a solo trip was not one I took lightly. Solo river crossing lacks the stability of crossing with a partner or team, as well as necessitates self-rescue in the event of being overwhelmed or injured. I wished I'd had a hiking pole and eventually made one, by whittling down a small tree branch. The decision to travel in autumn did significantly mitigated risk because the rivers were low. A lack of recent rain also helped. That said, warm temperatures increased water flow - the rivers are all glacier-fed. Most rivers were clear, so I could see lose rocks and boulders. More challenging than the river crossing at Muddy Flats (mile 12) was negotiating the steep slopes, much of which was laden with fridge-sized boulders barely held in place by loose sand. My greatest fear was that I'd get pinned or crushed climbing out of the river. I took me over an hour to find a suitable place to get up a small ridge without overly exposing myself to rock fall. That was the only very challenging crossing, all of the rest were straightforward.
Two hours after that, I found a lovely campsite at mile 16 and just below McNeil Point. I made a fire, put up my tent, strolled through the woods near camp, got some water and surveyed the route I'd followed all day. As the last rays of sun shot through the forest, they painted the west side of the mountain in pink and orange alpen-glow and made a perfect end to a wonderful day.