I have discussed Halloween with a number of good Christian pastors and they uniformly believe that it has its origins as a pagan, anti-Christian holiday.
I would encourage anyone to do a search on the origins of Halloween. If you are a Christian, you should not participate in Halloween in any way.
If you have Anglo-Celtic-Nordic ancestry like a good bit of us here, that pretty much sums our people up 1500+ years ago. I guess those people were damned in hell fire?
In Parochial school...we prayed for those souls in purgatory ...and Mass was mandatory on All Saints [Nov 1st] and strongly encouraged on All Souls Day.
Most Christian holidays have their roots in pagan festivals. Early evangelists simply co-opted the festivals and repurposed them with Christian themes in order to gain converts.
I do not care what the origins of Halloween are; the Christian holiday that was imposed on it is the eve of All Hallows' Day (aka All Saint's Day). Early Christians believed that the devil and his minions ran rampant on the eve of the sainted day, and so dressed up in scary costumes to scare away the demons. We have shortened "All Hallows' Day Eve" to "Halloween" but we have partially retained the rituals. However, I am not certain that the sight of a 6 year old dressed like a storm trooper is going to frighten demons.
What about Christmas? It was originally a pagan holiday as well.
I don’t care about the origins. If a kid wants to dress up in a costume and get some candy, then so what. We did it when i was a kid 100 years ago, and no one had a problem with it.