I start looking for a place to stay the night at 2:00 pm - mostly due to "blue collar Miller time" hits the back roads soon after that. I like to get an early start and an early stop. This is my style. I almost never get caught out looking for a hideout. And I can afford motels and private campgrounds.

Others wake up late, leave camp late, and bike until it gets dark. With the last few moments of light they find a spot to hide - most often on private property. Another issue is that many parts of the USA close up their state parks and campgrounds after Labor Day. For those who can't afford hotels there is often little choice but to hide out at night.

So if by "poor planning" you mean that every bike tourist should be rich and only tour at times of the year when there are ample services open and available, then you are correct. For those on a budget or trying to stay on the road for months or years, the allure of a FREE spot to hide out is very tempting. Yes, they are breaking the law. So long as they don't burn the woods down in the process and leave no trace of their stay it's difficult for me to get all ruffled about it. I know a guy from Australia who paddled a kayak down the Mississippi River from Minnesota to the mouth of the river and camped on the river bank without permission every single night until I put him up at my house in New Orleans for a couple nights. He never got caught, and no one cared to catch him either. It can be done, and some travelers really don't have a problem with doing it. It's not for me, but I find it hard to care.