At a Scratch-and-Dent sale, I found some Asolo Double Boots (don't know what kind, they were dark green) that fit my friend perfectly. She wants to use them, but most of the stuff I do is in the summer, and not higher than 11k ft.

Looking for a good trip, I suggested South Sister at the end of this month. I live in Sisters, and have been up the Central Oregon peaks plenty of times in the summer. However, this would be my first winter ascent of any peak above 7,000.

I know weather is key. If it looks bad, it's a no-go. But any advise on winter mountaineering, and this mountain especially?

Whats your plan of approach? skiing in, snowmobile, or hoofing it from dutchman? How much snow do they have there this year, man I miss seeing the 3 sisters on a daily basis. BTW I dont have any advice to offer but good luck!

You answered your own question with the variables mentioned, along with the above post that mentions your approach. It's a bit of an approach, I guess from any direction.
All depends on weather and conditions, and your time allotment and approach. Definitely doable if you know what you're doing and you've got the weather window. Sounds like you know what you're doing. . . Go for it the conditions are good and you feel you have the experience. Great places to camp.
Good luck.

roads closed at mt bachelor, so it will be one hell of an approach! ski in, or get someone to run you in on snowmobiles!!
or just take 2 days, maybe 3.

I was just up near Mt. Bachelor x-country skiing today. There is a lot of snow and it's really wet right now. It's supposed to get colder this coming week and snow is in the forecast all week. I've found that every feb. there seems to be almost a week of unusually good weather. If it was me I would hold off till then.

Depending on where you want to start.
-It's a 6.5 mile ski or walk from Mt. Bachelor, where road is closed, to Devils Lake campground and Trailhead. Then 5.3 miles to top.
-The Green Lakes Trailhead is an option to. It's 4.4 miles from Bachelor then roughly 7 miles
-Starting from Ductchman snow-park and heading towards Broken Top Trailhead is also a option but might be the longest option.

If you have the time and weather skiing is a great way to do it. A snowmoblile ride is much quicker and on a weekend it's not to hard to find one.

Oh and those boots sound like the same pair my buddy has, the AFS Guides? He's worn them on Mt. Jefferson and Mt. Hood in Dec. and loves them!

Good Luck anywho!

Yeah, I think the plan is to ski in to Green Lakes. Thanks for the snow conditions. I'm still deciding on the route as well, so if someone has a better suggestion...

Man, that approach is pretty long. It can be done though with good company and on AT/Tele's. As soon as you pass the X-country course, you can simply follow the scenic byway all the way to Devil's Lake or, you can cut that last mountain (Devil's Hill) and take a more direct approach via Goose Creek to the SSE flank of the Sister [warning: bring good flotation]. Remember, the days are SHORT and it's a long day if you wanna do this. I did it alone, last winter and it was an all out epic with frigid temperatures. However, it was so worth it. Total solitude, save for some snowmobilers on the byway and unprecidented beauty at the top:

Did you end up skiing the initial approach and how did it go?

I'm thinking of going March 20-21 but I haven't picked a route yet. I would hope to get a snowmobile ride in from Bachelor either to Devil's Lake or Green Lakes.

I wonder if snowshoes will be required or if crampons and ice axe will suffice. I guess it depends on the weather throughout the next three weeks.

I'm going to look into Broken Top. Maybe that is a bit easier in the winter with the road being closed and can fit into a weekend a lot better.