Well, the roadtrip plan has been postponed. As soon as I started looking for places to go backcountry skiing I realized that this area is not the most suitable for that. The thing is that most of the area is in the woods, so you don't really see where you are. If you want to be above the timberline, then you have to go to Mt. Hood, Mt. Adams, St. Helens... Besides you really need a ski buddy for that, so going alone to most of the spots it's pretty suicidal.
So this morning I drove to Trillium Lake. I got there early so I could avoid the crowds (it worked), and I would be cruising in a safe place, with plenty of marked trails. It was a nice morning, but really weird to be on my skis and not going downhill almost for a moment. That's good, I did something new!
Let's see what happens tomorrow.