About 10 years ago, I tried to get it down to $5 per trip to Wachusett for myself. I think the pass was $200 and I got on the hill for about 43 days or so... I don't recall. I am Mr. Cheap regarding skiing... I try to get deals and go to the smaller mountains more than the larger ones.
We did get $69 Loon tickets last year at the Ski Expo including the bus ride... but prob won't do that again