I'm regurgitating this old thread I started as I have the same trip planned this year. Last year, we ran into rain and (as we all know) very little snow so I never followed through with my plan. This year seems more promising.
My question is has anyone skied up the Black Cap Connector? I have found a few trip reports where it's been biked, and some of it is a snowmobile trail, so that is promising. My end goal is to be dropped of at or near the base of Cranmore Ski Area, with the hope of spending a day in the woods and finishing back at the base lodge. It appears that the Black Cap Connector (and the few minor trails at the start) to the Mt. Cranmore Trail is about 6 miles, most of which would be gaining elevation. I would then hop onto an easy trail on Cranmore to come down.
Thnx