Thanks in advance!!
In some ways its a bit like Timberline -- scale, terrain variety, pitch, etc. -- but with more reliable lifts .
Nightlife, restaurants, etc. are scattered throughout the small Berkshire towns in the vicinity. Not much at the base, at least a couple years ago.
It does ski a lot like Timberline. You are almost better off heading to Mount Snow, Stratton, or Bromley. These mountains are just up the road from Jiminy and offer a little more bang for the buck. I like the North Face of Mt. Snow. There's a short, but interesting run called, "Jaws of Death." How's that for a trail name?