Hit this on my 2000 AT thruhike and chatted up some motorcycle climbers reading the AT plaque. They'll have some good stories of the dirty backpacker they met.
Impressive views from the summit east down to the valley and of the summit (and Hopper Valley) from Stony Ledge. Made the visit with my parents and 94 year old grandmother ;-)
The Thunderbolt Lodge (1 room), refurbished in 1998, is surprisingly plush and looks like a great place to spend some time during the winter. There's even a fully stocked wood shed for use with the 4 wood stoves. Although you are not supposed to spend the night in there except for emergencies, it seems like it would be a lot of fun!
I came here once before on Dec 24, 2001 and attempted to hike up the gated (closed) 9 mile road but got very bored of walking through 1-2 inches of slush with 100' visibility so turned around about 4 miles up. I saw 2 x-country skiers and think that x-country skiing or mountain biking would be more fun during the winter if you want to take the closed road. Snowmobiles also seemed to be a popular method up from the tracks I saw. They also got a surpise 10 inches of snow on May 18, 2002 that temporarily closed the road to the summit. My 6th state highpoint after: NH, TN, NC, OR, and CA. Highpointing really isn't a priority for me but it's still fun :-)
Interesting little mountain in the scenic Berkshires. I bagged this state highpoint as a day-hike in 1994 and again during my Appalachian Trail thru-hike in 1995.