Hi thinkxingu, to beat the Lakes Region 'when snow conditions are good' 'KEY'.
Not easy to plan a ride so far in advance, however I would contact snowmobile Clubs in the areas you would like to ride in, and get their snowmobile Maps to study in the meantime. I've ridden in Ma, NH, VT, Maine and Canada, and haven't had a bad ride yet!
Best wishes to you and your's.
Terry