As a child, I was raised in a Christian community that did not observe Halloween at all. We might have given something to oddly arrayed children on our doorstep, but we never dressed up, never went out, and tried to do our best not to support the holiday. I didn't really care; my mom didn't give us kids candy anyway.
As a young adult, I learned a lot about the holiday from people who had done more than dabble in the occult. Whatever you might think of the legitimacy of their attempts to connect with the dark side, they were pretty serious about what they hoped to accomplish, and Halloween was their Christmas and Easter rolled into one. They told very dark stories about what happened during this holiday, the kind that keep you up at night.
As an older adult, I have moved out of that community and come in contact with a lot of other sincere Christians who view Halloween as just another holiday. I have revisited my long held opinions over the years, and while I have not changed much in my opinions, I have realized there are at least two ways Christians view Halloween that are strikingly different, but solidly supportable.
1) The Bible says that, because of Christ, death and the grave have lost their sting. Any victory they have over people is temporary and hollow. The Bible also says that while Satan is like a devouring lion, he is nothing in the face of the power of God. To some Christians, Halloween is a time to mock the hollow power of the grave, to laugh in the face of death. Elijah mocked the prophets of Baal; why can't modern day prophets mock the false idols and gods of our culture too? The only thing the Bible tells us to fear is God, and if we can't laugh in the face of death and the grave, then we don't understand the power of God. Sure, people dress up in the costumes of the denizens of evil...so why not dress up like Cinderella and trivialize the impact of the dark? Evil's power is felt most strongly when it control us; why not take the one holiday that celebrates evil and make fun of its attempt to be so macho and scary? We are the people of light; we ain't afraid of no ghosts!
2) The supernatural world is very real, and the the realm of darkness is dangerous and destructive. God is a God of creation, order, goodness, life and light; evil promotes chaos, destruction, death and darkness. Halloween trivializes the seriousness of the stakes. It's one think to mock evil's false pretense; it's quite another to join the celebrations in which we scare ourselves and mimic the things that we know to be wrong with the world. We get upset when the the Easter Bunny and marshmallow peeps distract people at Easter, because there is a real message that goes with Easter, an underlying truth of eternal significance. We get upset at the commercialization of Christmas, because it distorts or obscures a message the needs to be heard. And yet at Halloween, we contribute to the trivialization of a reality that ought not be made silly - and certainly not celebrated.
There are middle ground positions, but I think that captures the poles. I have friends who defend both sides with equal vigor and capability. My point is not to tell you which one is the right one (though I suspect you know where I stand). If you observe Halloween differently than I do, more power to ya'. Just don't gloss over the fact that our decision ought to be well informed and purposeful.
As a postscript, here's my short list of reality checks:
1) If you believe in the supernatural world, you cannot just say, "Oh, it's only fun and games and dress up. Lighten up." You have to grapple with the fact that it is the one holiday that highlights the entropy and chaos in the world. You may end up legitimately choosing either of the above approaches, but you can't do it lightly.
2) It is the holiday that gets the most overtly destructive responses from people (see here, and here, here, here, and here). When killing cats, committing arson, and just in general making law enforcement buckle up are things that logically follow from the holiday, something is not all right. Here's what you get in Canada:
56% — The proportion of all criminal incidents reported during Hallowe'en 2006 that were violations against property.
18% — The proportion of all criminal incidents reported during Hallowe'en 2006 that were violations against the person.
11% — The percentage increase in Other Criminal Code violations such as weapons-related offences, public morals and disturbing the peace reported during Hallowe'en 2006 compared to a week earlier (i.e. October 24, 2006).
38% — The percentage increase in violent offences such as robbery, aggravated assault, assaults causing bodily harm and assaults against police officers reported during Hallowe'en 2006 compared to a week earlier (i.e. October 24, 2006).
22% — The percentage increase in property violations, including general mischief and arson reported to police during Hallowe'en 2006 compared to a week earlier (i.e. October 24, 2006).