I’ve been going to Wachusett for 30+ years(!) For the last 12 it’s been especially great for my kids to learn on and develop some skills to build upon, and have some great family times together. My son and I now go twice and sometimes 3 times a week. I was truly heartbroken to report to him that we may need to change our plans this season as passes are sold out—- because I snoozed, and might be the worst parent on earth. I wouldn’t have ever imagined this happening. We are unable to align with the session times nor can we afford it going at least 25 sessions each. The only available pass option option left is to buy 2 Corporate passes at $1300 each. At this point I am another guy who would be looking for 2 Bronze passes and willing to pay a premium for them.
I spoke with a friend that works at Wachusett. He believes it would be a no-go to transfer passes between individuals. Company policy. The only pass that is transferable between individuals is the $1,300 dollar pass.
Forget the 3.5 hour session tickets. It would cost you a fortune unless you only ski 2-3 times per season. Plus, they just raised the weekend session tickets to $72 for 3.5 hours of skiing. The also raised the reschedule session fee to $24 from $18 last season. He told me people are madder than hell over this. He is also ticked off because he was told that they are planning to reduce his work hours this season from 8 hours per day to 3.5 hours (to match the session time he is scheduled to work).
Being in Medway, MA, you are not exactly close to ski country. I imagine it takes you close to one hour to get to Wachusett. It is going to be 2.5 hours to get to Berkshire East and Butternut from there. You might as well just travel north up to Crotched, Gunstock, or Sunapee.
I feel sorry for you and your son. Most people don't even start to think about skiing until Fall starts. The same thing happened to my friend. He ended up getting an Epic pass for his family. I think they are still available, but you missed the discount period. Good luck with what you decide.