"And because he considered that they who had fallen asleep with Godliness had great grace laid upon them, It is a holy and wholesome thought to pray for the dead that they may be loosed of their sins. 2 Machabees 12:45-46 (D-R)
The proper name for Halloween in the western Christian tradition is "All Hallow's Eve", and in short, Yes, it is ok and even proper for Christians to celebrate this day. All Hallow's Eve is a vigil that is held on the eve of All Saints Day (November 1) which is primarily to remember the Holy Souls in Purgatory, and on All Saint's Day we remember the saints that have left this earth to be with the Lord, at least in spirit, in heaven. Those who observe All Hallow's Eve should be sure to remember that this is a day of remembrance for those Holy Souls in Purgatory. The Holy Souls in Purgatory are assured of the glory of God, they will not go to hell but the more we pray for them the sooner they shall see His Holy Face.
As far as trick-or-treating, Halloween parties, or dressing in costume is concerned I don't see a major problem. Of course we should avoid the demonic and all things satanic in nature, but all things remembering the dead are, in my opinion, proper for this day. A display of graves, visiting cemetaries, dressing as ghosts or dead souls, skeletons, skulls, bats, jack-o-laterns, and other traditional symbols of the holiday are merely pious observances of the holiday. On the other side, devils, demons, serial killers, and other forms and symbols of evil should be avoided because by this display of solidarity we glorify evil and open doors to the same.
In the end, no matter what you do this All Hallow's Eve the primary focus should be the Holy Souls and a remembrance of departed family members and those who have gone before us. I believe that nearly everyone has the potential to be a Holy Soul in Purgatory. Not that everyone IS a Holy Soul, but we all have that potential. The bottom line is that in reality we never knew their private souls, their confessions, nor their penance before God, so who are we to judge? It is just and holy to pray for all the souls who have departed this life no matter what our earthly perceptions of them may be. Our perceptions maybe right and the may be wrong, either way our prayers are holy and just.
Byzantine Chant for the Dead: https://www.youtube.com/watch?v=NgriVVhCM3c
Matthew Joseph Abraham
Amen
