I've been looking around for possible trips to do around Christmas time. I got a pair of snowshoes as a gift so I'd really like to try those out. I live near New Haven, Connecticut and the closer the better.

Potentials:
Mt. Greylock area
somewhere on the AT near the CT portion
somewhere in the Gunks
Killington Area, but a bit too far away

Any ideas are welcome, probably in the 20-50 or 60 mile range, but open to anything!

I don't know about you, but in the winter my top two criteria for snowshoe hikes are proximity and access. During the winter, I rarely even see tracks after 1/4 mile down the trail. So, almost anywhere close by with a good parking lot will do for me.

All the options you mention should be fine. If you do want to go to VT, I wouldn't bother going to Killington. I'd think that Route 9 to the Glastonbury area would be better. You could go up the firetower and get a good view of the Somerset Reservoir. Another nice route might be south from Manchester to Stratton Pond.

Of course, during the winter I'm never too concerned with mileage or getting to the top of anything. I just like taking a nice walk in the woods with a few friends and my dog.

Good point about less busy trails. Still forming my criteria, so I'll steal yours and add legal camping and enough snow that I don't feel silly snowshoeing. Or ditch the snow shoes and find somewhere warmer. I'll check out the Glastonbury area and Stratton Pond. I went through Stratton pond a few months ago during my attempted LT thru-hike and its a very nice area.

Thanks for your help Thomas