In reply to RusseyB:
I've climbed during every month over the years, and in almost all conditions. But now I'm old and fussy and demand premium rock-climbing conditions, which happen quite a bit in the winter but can't be predicted.
The deal is that the main cliffs face SE and so get direct sun from the early morning until about 2 pm. By 9 am or so, the rock has warmed up and then a layer of air next to it, so the cliff face can be considerably warmer than the rest of the area---this means you can't judge the day from anywhere but the cliffs themselves. All the nice heat goes away fast once the sun passes over the ridge and the cliffs go into the shade.
So, the climbing is good on any bright sunny day from, say, 9-2. Such days can be as good as you can get, with the air crisp and the crowds away. But as I said, I've become picky in my dotage and so can't be pried away from the hearth unless, in addition to the bright sun, the temps are also above 40 (F). Some years there are lots of days like this; other years there are hardly any. In any case there is very lovely hiking.
Ragged and some of the other Connecticut crags are nice but are no match for the extent, variety, and height of the Gunks. I'd say the Gunks would be the best bet in the winter by far.
I'm a professor and won't be teaching during the Dec/Jan time period you mentioned, so I'd meet you for a bit of climbing if you'd like---if the conditions are right for me...
