I would recommend grabbing a plate of cookies and chatting them up. Most of the farmers I've spoken with are happy to talk about what their doing if someone is actually interested and they have even a moment of spare time. If you hit it off you might
be able to ride along when they till/plant in the spring(it can be a super high stress time if the weather isn't cooperating and your three weeks late planting).
I'd also try to avoid going into the relationship trying to change what their doing (this sounds like dating advice
) first learn what it is they are actually doing and why; if they are highly educated then they are probably managing that field in a specific way for some specific reasons, not all of which are immediately obvious. After some time you'll have gotten enough background to be able to look at the field from the farmer's point of view as well as the landowner's. If you get to know them before hand there is a good chance that you could pay them to plant/harvest the crops, perhaps they could even help you sell them.
Hmm, maybe avoid talking about putting trees in the middle of their corn field at first.... personally I did not get a happy response to that one ( it only takes 1 machine to kill 1/4 million trees/it only takes 1 tree to kill a $1/4 million machine)
Maybe instead talk about planting sugar maples on the field edges
is a middle ground between Conventional Ag and Permaculture, there is a chance that he or another neighbour already does some of these things. Cornell University
also has a very extensive agriculture out reach program, much of it applicable to your growing area.