First, I suppose we have to move through the negative before we get to the positive.
I have yet to find any good arguments for not celebrating Halloween. They might seem like good arguments until you try to be consistent. For instance, many from my past argued that it “comes out of paganism.” But if you are consistent in the belief that “we should never celebrate something that had its origins in paganism” then we must do away with Christmas and Easter as well, something these same folks are not willing to do. There are others who would argue that we should not celebrate Halloween because “it celebrates evil.” The problem with this is that Halloween is not a person. “It” doesn’t celebrate anything. We have learned from Christmas, that holidays have different meanings for different people. If you are a Christian, Christmas means something to your Christianity. But if you are not a Christian, Christmas means something completely different. I do not own the calendar. If people want to celebrate family on the day that I celebrate the birth of Jesus (both in history and in my own heart) they are allowed. There is no “objective” meaning to Christmas (as evidenced by the fact that December 25 was not chosen because it was the date that Jesus was actually born as well as the fact that it wasn’t celebrated for the first several centuries of the Church), it is a cultural phenomenon. I celebrate it because it means something to me. This also means, on the “opposite” end, as holidays go, there is no “objective” meaning to Halloween. I am free to celebrate it however I wish. If I am a Christian, I will celebrate it Christianly. If I am a pagan, I will celebrate it paganly.
But this is not enough. We should not just “tolerate” Halloween, giving our kids the uneasy “okay” as long as they dress up like Bible characters. No, we should be one of its biggest supporters. Halloween is a friend and ally to Christianity. Why do I say this?
I only say this because I assume one thing: the primary enemy of Christianity in our culture is no longer other religions but a lack of imagination (which ironically, many Christians also suffer from in our culture). It is the inability to see “the possibility of another world.” Along with the beauty of science often comes a mindset of cold determinism, that “what you see is all there is.” A worldview where there is nothing more to love than firing neurons and chemical imbalances. That all there is to poetry is the evolution of language. That if we cannot see the afterlife it cannot possibly exist. It is not paganism that will topple Christianity but a lack of imagination, a depreciation of art, an inability to think of mystery as a positive rather than something to be attacked and eradicated.
And if this is true, then Halloween is on our side. As Christians, we meet weekly to remind ourselves that the world of “what we see” is not the world “of all there is.” But Halloween is a tradition that the entire world celebrates to excite the imagination, an affirmation that what we see is perhaps not all there is. It is the celebration of the possible. The entire world gets to, for just one day, live in a world where orcs and hobbits exist, where The Force is real and evil will one day be vanquished. The entire world gets reminded that maybe not everything can be explained away. We get to affirm what a growing number of us only reluctantly admit from time to time: that maybe, just maybe, our story really is bigger and better than meets the eye.
If you want a more traditional “refutation” of Halloween, see this great article from Christianity Today 2000: http://www.christianitytoday.com/ct/2000/october2/29.79.html