To be honest, we haven't actually talked much about Halloween, because neither of us have celebrated it since we were very young. I can remember one Halloween dressing up as a fairy princess, and the next year Mom and Dad were all set to dress my brother and I as Thing One and Thing Two, when they decided that Halloween wasn't something they felt comfortable celebrating any longer. For Caleb, he was six when he moved to Romania as a missionary kid, and when you're living in a place where contact with demon-possessed people happens, you really don't want to join into the yearly celebration of them.
But is there a place in a Christian's life for scary stuff, or do we need to shy away from anything considered "dark?" We've been tossing that one around for the last couple of weeks, and I was very excited to find a post on one of my favorite blogs which laid out the exact conclusion we'd come to. Here it is: http://www.rabbitroom.com/2011/10/righteous-horro/
And if you like reading books set in your current season of the year, try out one of my very favorites: The Perilous Gard, by Elizabeth Marie Pope.(You can get it used for a penny on Amazon, plus shipping...) In my opinion, she brings a beautifully Christ-centered perspective to All-Hallows Eve in a very skillful way.