RE: eastern shore descent

Would you say late September, early October would be a good time frame for the trip. I hope to start at Harve De Grace and cross over to the east side at Elk Neck and on south to Cape Charles. You are saying that it would be tricky camping past Kent narrows? I was thinking I would need three to five camp sites in that stretch. Are wildlife perserves off limits or would I be able to leave no trace in those areas. What are the specifics of property ownership at the waterline in the bay, Md vs. Va. This would be a dream trip for my 50th bday and would be coming from Colorado so I would like to know if this is possible or would I be getting hassled along the trip. Are there any campgrounds at all along the eastern upper bay that are legal?