I went trick-or-treating as a kid. I really enjoyed it, especially before I was ten or so. Sometimes when I think about having kids (God willing, but not within the next nine months, if you catch my drift), I think about taking them trick-or-treating, and so does TH.
But I really think it might be seriously assur (prohibited) to do so. I mean, first of all, this is a holiday that began as a Christian holiday (eve of All Saints' Day, November 1) and is now seriously observed by some as a pagan holiday, although obviously most people don't celebrate it in any kind of religious way. If there were no pagans anymore, that would be a different issue, but there are people who claim that they worship the devil or the sun or what have you. How is dressing up on Halloween different from observing XMas or Easter in some way? I am not including going to church in that, because going to church is so obviously not okay that it is not analogous.
Last year, I read what R. Student had to say on Hirhurim about just passing out candy to non-Jews. I realize that R. Student tends to be way to the right of me hashkafically, plus I live in an apartment in NYC and don't have to deal with it. I also don't get the point of adults dressing up for Halloween (I try to get into it on Purim, but it's hard), so I'm not worried right now. But I am curious.
So what do you guys think, beloved readers? How comfortable are you with Halloween? What does halakhah as you understand it have to say about it?