The way I remember my mother had explained it, traditionally Halloween for us fell at a time when the nights were growing longer, cruelty of a long winter approaching like wolves, and the veil between the worlds would grow thinnest and the ghosts of the hungry dead, monsters, and dark elves could step through to do harm the family. So we would leave offerings gratitude at graves and in ancient hillsides for the bountiful year and that night we wore masks to disguise ourselves as something monstrous to frighten them, carved jack-o-lanterns to find our way home but as well as to bribe the mischief and the danger at the door from crossing the sanctity of the threshold with offerings sweets and fire.
It seems terribly funny now that I'm older, but soon I'll be carving jack-o-lanterns for my first home. Perhaps there is something to be said for honoring these traditions.