Hey, I grew up in Butte. I haven't lived there in a while but here is what I know. Hope it helps.
This is Red Mtn it is very close to Table Top http://www.summitpost.org/mountain/rock/153185/red-mountain.html this is in the highlands. Yes this can be done in winter, I know a couple guys who have done it. Don't think avalanche danger is too bad. Access can be the tough part. Also on I-90 east near Homestake pass and CDT there is a nice network of trails. Not many significant mountians near the divide and pass though. Some great rockclimbing though. There's a nice guidebook to all of the climbing around Butte. Oh and of course you can't miss hiking to Our Lady of the Rockies on the East Ridge. Kind of Bizarre, think Christ the Redeemer in the Rockies and instead of overlooking the ocean it overlooks the largest superfund site in the country.
The Anaconda/ Pintlars are in Deerlodge N.F. A good guide is, Hiking Anaconda/Pintler Wilderness by Mort Arkava. And yes there are plenty of trails.
Mt. Haggin is near Anaconda and a great peak to hike year round. I've done it once in winter. Here is my simple page of it http://www.summitpost.org/mountain/rock/549168/Mt-Haggin.html
Then of course the Tobacco Roots I absolutely love this range. Although limited it can be accessed during the winter. Near the town of Pony you can access Hollowtop Mtn for great views of the range. Also near there is Norris Hot Springs. This place is fantastic but only if you like good people, music, and beer. http://www.norrishotsprings.com/
Between Butte and Dillion West of I-15 is the Pioneers. There are plenty of big peaks in this area to keep you occupied. If your a fisherman it's paradise. It has some of the best trout fishing in the county.
A couple of general guidebooks are the Falcon Guides- Hiking MT, and Wild MT. While some people might not like Falcon Guides it was started in Helena, MT and Hiking MT was their first book and was written by Pres. Bill Schneider. I think it's great.
Again hope this helps. If you want anymore info don't hesitate to ask.
Oh and if you there in a couple weeks for St. Paddy's day be forewarned it's absolutely nuts but in a good way.
