Mike P, thanks for the anecdote about N. Twin and snow depth... hadn't thought to consider that this might be a factor in shelter! Never heard of those non-Whites ones you mentioned but I appreciate them; I'll be traveling a bit in the next few weeks and may be in the Northampton MA area with some free time, so might well be looking for something to do in that area.
Hi Harp:
If you go to Northampton, I highly recommend Mt. Tom, nearby, approached from the north side on the New England/Metacomet-Monadnock Trail. I'd say only go in good weather - it's no joke, and you're walking along a cliff-line - a beautiful one, at that, with magnificent views to Monadnock in one direction, the Greens in another, Greylock in another and Greater Hartford and Springfield to the south. Unless everything melts, which I doubt, you'd want to bring along all equipment. The southern approach via side trails to the M-M and then the M-M itself is quite steep - the grade is over 30-50% for much of it, though the nice thing is that you get to the summit fast. Maybe go up it, but I'd say not down in winter, certainly not in ice, without crampons. A loop hike over Mt. Holyoke from the west side would also be nice, as would Mt. Norwottuck - Holyoke, though a couple hundred feet shorter, has much better views. Mt. Toby's very good hiking, too, and it has nice views from the fire tower at its summit. Though it's higher than Tom and Holyoke, I think they are much prettier and have more dramatic views, especially Tom.
To Mike's non-White recommendations, I'd add Greylock via the Hopper Trail and the A.T. (or the roads). I found the Hopper Trail pretty easy last spring. It has some stretches in the 20-25% grade range, but it would likely be well beaten most days and is a very pretty trail, prettier than Cheshire Harbor, of which I've done the upper half. C.H. would be easier, and the road walk option up high would kick in at about the same place as for the Hopper Route. If you go up Hopper, I'd recommend there-and-back, with Overlook Trail as a possible variation - it reputedly has awesome views on its more level stretch, which I haven't done yet. I have done the part that descends off the cone, and it's not too bad. The problem with looping via the A.T. and back down via Money Brook Trail is that the latter trail is rough and steep. Not saying not doable, but I found it a knee cruncher. It is a very beautiful trail, though, and in the winter would be a treat. You could look at going up it and down Hopper, as well. The State of Mass's Greylock Reservation site is excellent, with good maps and route recommendations:
http://www.mass.gov/dcr/parks/mtGreylock/brochures.htm
Also, re: Everett, the Race Brook Falls Trail is quite steep in places but extraordinarily pretty, any time of year, and especially in winter. I played around there twice in the winter of 2010-11 and had a ball in all that snow. Took a ton of pics, if you're interested, which appear very early in my Panoramio stream - lots of neat ice sculptures amid the waterfalls, of which there are 6. It's a very popular trail and likely to be well packed - it's a route to the A.T. between Everett and neighboring Mt. Race, both of which are beauts. Everett's southern ascent might be quite difficult in winter, expecially if icy - there is one stretch at 40-50% grade, a few hundred yards long. I'd expect the trails to be easy to follow, but I've only gone as high as 1800', to the top of the falls, in winter. Everett's at 2602', Race at 2365'.
Take an ice axe--among other uses, you will need it for hooking trees and pull-ups. Hi Cannon is a bit tamer--however, we have used a rope to help beginners up the ladders. (Come to think of it, a rope might be handy for belaying on the KRT... 
