Next season will mark 30 years in Montana. A big eastern trip would be fun , all the ones you mentioned plus Smugglers , Saddleback and a handfull of Quebec hills. I skied Mt Greylock once in 1977.
Sunset at Camden Ski Bowl and a seafood feast sounds like fun to me. I love the people and geography of coastal Maine , the sound of diesel engines starting just before dawn while smelling pine needles and low tide.