Catholic Fire furnished this tidbit of information:

"The vigil for the souls, as well as the saints, had to be kept on this night because of course the two days were consecutive feasts — and a vigil is never kept on a feast." So we are midnful of the Souls in Purgatory as well as the Saints in Heaven tonight. This would indeed be spooky: "Breton families prayed by their beloveds' graves during the day, attended church for 'black vespers' in the evening and in some parishes proceeded thence to the charnel house in the cemetery to pray by the bones of those not yet buried or for whom no room could be found in the cemetery. Here they sang hymns to call on all Christians to pray for the dead and, speaking for the dead, they asked prayers and more prayers."

Catholic Culture echoes this point well:

Halloween is the preparation and combination of the two upcoming feasts. Although the demonic and witchcraft have no place for a Catholic celebration, some macabre can be incorporated into Halloween. It is good to dwell on our impending death (yes, everyone dies at one point), the Poor Souls in Purgatory, and the Sacrament of the Sick. And tied in with this theme is the saints, canonized and non-canonized. What did they do in their lives that they were able to reach heaven? How can we imitate them? How can we, like these saints, prepare our souls for death at any moment?

Anchoress makes a good point [via Happy Catholic]:

So, you see…Halloween is a big happy day in this house, and that is precisely what this lady at church did not like. I was excitedly discussing our Halloween plans at a meeting one night, when this woman told me I was being used as a tool for the devil “to make evil ordinary.”
I told her that evil is made ordinary every single day on television and in movies and in how we treat each other, and that my gleeful Halloween antics had less to do with making “evil ordinary” than in proving that externals are mostly powerless over us, except as our own minds and souls perceive them. I said, “mock the devil he will flee from thee…”

Young Fogeys points the way to EWTN's special feature on Holy People.

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