Jordan, one thing I was thinking about at work today was if you had considered planting some balsam fir/scotch pine/white pine/etc and get a future christmas tree farm going? That way, when people come out to pick pumpkins/apples they will know that you've got their 'full season' needs covered with halloween/thanksgiving/christmas. Obviously wouldn't be until later down the road, but it's something to build on. Could always entertain some sort of christmas deal as well such as sleigh rides, or sell your chestnuts and trees during december. This breaks the season up a bit.
Sweet corn for late summer/early fall, apples for all fall, pumpkins for october(maybe a maize maze...that'd be amazing ;)), take november off, prepare trees and such for christmas in the years to come.
If you get into the projects mentioned ,, Apples, pumpkins, Christmas trees, corn maze , hay rides, There is absolutely no way you will have November off, in order to make these projects large enough to positive cash flow there will not be enough time to care for the details to make it a first class experience for your customers , Skimp on the little things and the public will take note . You may find it hard to deer hunt . time , commitment ect
Love to watch your progress