First, check out this map:
http://www.pcpg.org/images/pennmapmid.jpg
The counties with the (blue) Devonian formation running through them are the most likely to have chert. If your county doesn't have this running through it I would still look anyway.
As far as digging goes- for me it is too much work. The best way would be to look for some type of outcropping or an area where the geological layers are visible, even if it is only a few ft. of it. I really think digging will be to hard and it may be an impossiblity. You will have much greater access to the geology if you locate an area with visible layers or outcroppings.
Don't forget a hammerstone for quality testing! (I only say this because I can never find one I like in the wilderness when I need one).
Let me know how it turns out and if you have any other questions that I can help you with. Also, if you need some help with knapping or getting quality knapping tools let me know. I am by no means an expert but I can help you get over the small issues that are a pain to figure out on your own and usually discourage people from knapping.
"Yet, he was able to do in two hours what nine cops, a bloodhound and a guy in a helicopter could not do in twice that time."