"Black Fly season lasts, on average, from Memorial Day to the Fourth of July. The season will start earlier in some parts of the state, especially southern Maine, and end later in northern Maine. Black flies are mostly found in wooded, wet areas with with large amounts of standing water. Summer breezes are your best insect repellent as the flies like hot calm days."
Sounds like I'll probably be up there late in the season, depending on the weather. We have a cabin at a similar latitude over in Ontario, and the flies are usually not an issue past about the 20th of June. But I don't know in Maine. I'll bring long sleeves just in case.
Also, I definately do not want to overplan. I am not really going to bother with a schedule or anything, but everything you guys are mentioning I am circling on the map. I'll do some planning the night before and see what happens. AZ had it right when he said there is a happy place between not planning and overplanning.
I have a question, what do you guys know about tent camping? And NOT on a campground, I mean back in the woods, maybe a half mile off the road near a creek at a NF or NP? The questions I have mainly are where do I park my car and how do I not get in trouble? Everyone seems to like camping at these organized campgrounds, I just don't understand it at all. I want to hike down a trail and find a spot, pitch my tent and not have to deal with other people. This trip is just me, my dog, and nature. I want to see as few people in between as possible! Is that weird? I guess the issue is they're trying to keep the masses out of the forest to protect the environment, but I'll leave wherever I go looking better than it was when I got there.