My second attempt, and turned around again due to clouds.
10/8, Saturday. Thick clouds in Portland. Weather forecast for South Sister area is partly sunny for the weekend. However windy at higher elevations. I rented a car and drove south. Rental agency doesn't open until 9. So a late start. It's a 4 hour drive including a toilet break.
Parked at Devils Lake official trailhead. It's on the wrong side of the highway. Unless you camp here, it's easier just park by the road, where the trail picks up on the right (north) side of the highway. When I filled a wilderness permit, it was already 1:30pm. So I hastened my pace. Less than 30 minutes into the hike, I hit snow. The trail is easily visible by the bounding of passing boots. It was wet, slushy, and slower than I needed to summit, which is 6 miles and 4900' up. The sun sets at ~6:30pm this time of the year. 1 hour from TH, you break out of the trees. Soon a trail junction. The trail westwards is signed to Wickiup Plain. A few minutes later, another trail junction. The one NE signed to Moraine Lake. It's quite pretty here, but wet. You can see Bachelor, Broken Top, Moraine Lake below, and Sparks Lake far south. I met a group of 3, of which I know 2. Chatted for a bit. They turned back at around 8000'. We couldn't see the summit at the time. As clouds moved in and out, I continued. The trail isn't steep. More rocks and more exposed as you go higher, and the wind got stronger.
Around 5pm, I got to Lewis Glacier. Very windy. I had to cover my mouth or turn my back in order to breath. I continued along the right to the left of the pond for another 20 minutes, and turned back. I was at maybe 9200' according to the GPS location. As you could see the photo on the left, visibility was getting quite low. The summit is at 10358', and maybe 1/2 mile away.
Quite colorful western sky under thick clouds. Saw a camper with fire in the plateau above Moraine Lake (not sure if open fire is allowed, but with so much snow, it poses no risk). The night set quickly after. By the time I got back into the woods, it was quite dark. With the half moon sometimes out of the clouds, I could see a bit. However, at some point I lost the trail. My headlamp was getting quite dim. It took me quite some effort to stumble out of the woods and on to the road, aided by the GPS map on my phone. Even with gaiter and waterproof boots, my socks still got a bit wet.
I drove to Todd Lake parking area. No energy to check out the campground, even though I knew it was a short walk, because I wasn't familiar with this location. Slept in the car.