I realize that a lot of kids dress up as princess and Jedis. By and large, though, it is a holiday celebrating fear and death. The media likes to program stories about "spooky" music, and interview paranormal investigators (who are given no credence as anything but laughable other than during this time of year). People decorate their front lawns with skeletons and graves. Halloween movies are about monsters.
For this reason, my wife and I chose not to make Halloween part of our family. While a lot of it is silly spookiness, we both feel like any celebration of fear, darkness, and death is a step on a road we do not want to walk down or launch our kids on.
I'm disturbed by the fact that movie theatres are filled with horror movies around the year now. I'm also troubled by how far the line has been pushed on what kind of gore, death, and monstrosity is acceptable to be displayed on billboards, shop windows, and restaurant decor. This is the kind of thing that people find themselves moving toward more and more shocking things because their hearts grow hardened from exposure.
Having said all that, I'd never condemn a fellow believer for celebrating Halloween, but I'd have no problem sharing my concerns and the journey my wife and I went on from big Halloween fans to now.
Our kids get at least one big, treat-filled, joyous costume party a year when we celebrate Purim together with friends. They also like to choose costume parties for their birthdays. So far they haven't expressed any disappointment at not being able to be a part of Halloween.