Halloween customs have meaning.
We may think of Halloween customs as being simply part of the fun and games of dressing up and celebrating the macabre. However, these ancient customs have sometimes very serious meanings. Yet, many of them have been adopted and incorporated into modern culture.
Costuming and walking around dressed in costumes is a tradition centuries old, but there are many possible reasons for it. Some origins come from open-air plays normally held on Halloween. Other traditions come from dressing up as scary things to scare away spirits or to scare other people. Still, some customs come from dressing up as the dead to trick them into thinking you’re one of them so they’ll leave you alone.
Gourds and other large, hard vegetables were carved with scary faces and illuminated with candles to scare off the wandering spirits. It may also come from an Irish legend of Stingy Jack, a man who tried to cheat the Devil and ended up roaming the earth with a hollowed out turnip for a head. However, the American pumpkin made using squash a favorite. In fact, the jack-o-lantern may have been the head the Headless Horseman wore in the Legend of Sleepy Hollow.
Children dressing up as scary spirits and going around demanding sweets or money house to house is an old tradition. It actually exists in quite a few cultures. However, it didn’t really pick up as a thing all children did until about 1920, and unfortunately, it’s on the decline. For many children, it was the one night a year where they ruled the community, where they could exercise power, roam the streets, and make demands of adults. However, it has its origins in children mimicking spirits who would demand payment in order to not torment, or “trick” the family living there. The adults, playing along, would pretend to be scared and give them candy.
However, going house to house and asking for alms in exchange for prayers or blessings, and threatening to curse those inside who did not give them money is a very, very old tradition.