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Hmm that is pushing the boundaries of being legal, and if he is charging for the passes he is opening himself up to liability/lawsuits.
Maine has a great law that in most all cases, exempts a landowner from liability if someone is injured on their property, as long as they don't charge to use that property. As soon as you charge a fee, you lose the protection of that law, so then you are at the mercy of the courts. A liability waiver may or may not work if you are charging for the use, I am not a lawyer and won't pretend to be one, but I would want a pretty good lawyer to check it out before I started charging people to use my land.