I think I saw that guy between #2 & #3 not raking but moving some leaves near a mall orange survey flag. My guess is some sort of biological survey of some sort.
Not too far separated, since the course had such a sharp angle at #2, so presumably the same guy. That is a plausible guess, and my other guess isn't that different, though less scientific.
First I thought it was Pete Bundschuh, but that was not the case. I then asked him if he was raking a trail, and he said yes. I imagine a new Mt bike trail.
OK, that makes sense, and maybe the pin flags were where the trail route had been marked out. (My other guess was that he was looking for morels.)
I thought the pin flags were for new bike trails. I'd assume that's why he was raking, but you never know... Trump's forest fire prevention force might be at work in NH.