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Taken from HowStuffWorks.com:

"Today, many caroling groups sing for charity in churches and neighborhoods; some historical accounts claim this is rooted in feudal societies, when poor citizens would "sing for their supper" in exchange for food or drink.

Another theory is that carolers traveled door-to-door because they were not originally allowed to perform in churches.

Others say this idea didn't develop until the 16th century, when Anglo-Saxon peasants adapted these pagan customs when they went wassailing, requesting nourishment from their superiors in exchange for singing good tidings.

Wassail was a thick, hot spiced beverage that helped keep the traveling well-wishers warm; in its heyday, the drink was just as much of a holiday tradition as eggnog is in modern times. As wassailing evolved, with children often going door-to-door, it became more associated with Christmas and caroling."

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