I respect that some Christians view Halloween as a holiday honoring darkness and evil and therefore anything Halloween related as automatically out-of-bounds. I am not a fan of Halloween and am troubled by how much our culture loves it. Having said that, it exists and we have to navigate it with our kids.
Redemption is about taking something sinful and transforming it into something that honors God. Christians have done this with other holidays (Christmas trees and Easter eggs have pagan roots but have been transformed by Christians into hopeful symbols of life).
While some elements of Halloween are clearly not of God, there is nothing explicitly sinful about kids playing dress-up or carving pumpkins. I think it is possible for children to enjoy those things in a way that doesn't cross the line into celebrating evil and death. Every Halloween I have sat at the table with my kids ans carved pumpkins with them, explaining the Gospel as we go. It has become a special family memory and has helped transform a dark holiday into something which points them to Jesus.
But if that's not something you are comfortable doing, I get it. Listen to your conscience and do whatever you think would best honor Jesus.
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