Few holiday traditions have endured as long or seen so many variations as that of wassailing. Its origins are unknown but it is mentioned in texts dating as far back as the 14th century. In one such text, the leader of a group took a bowl and, raising it to the crowd, shouted "Wassail!" an Old English term meaning "to your health".

There are three variations of the wassailing. One is the filling of a common bowl or cup often referred to by ancient clergy as the Loving Cup and passing it around a room to be shared. Another variation calls for taking the bowl around to each individual house so neighbors can partake as friends. And the third is a celebration of the apple harvest and the blessing of the fruit.

In the earliest known days of the practice, the wassail was poured on to the dormant crops and orchards after harvest to bless them for the coming spring and to ward off evil. Like many such practices devoted to the defense against evil, wassailing has always been a more festive activity associated with partying and making merry. In the last couple of hundred years the practice has been more about good cheer and well wishing than the blessing of the crops.

Wassailing is almost always accompanied by song. "Here we come a-wassailing…" is a Christmas classic beloved by many but understood by few. (It is so misunderstood that some sing "here we come a-caroling…" instead).

The actual ingredients in traditional wassail are widely disputed. This could be attributed to the fact that festive bands of people who traveled from home to home often replenished the bowl with whatever liquid was refreshment available. While one home might have apple cider another might have spirits of a stronger sort. Alcohol has no doubt played a storied part of wassail's history, but tradition does not dictate it to be necessary. In fact, the custom has little to do with the drink at all than it does the good will and society that wassailing generates.

Wassailing, while classically observed during the Christmas holiday season, is also practiced at weddings and other such events where community and family are celebrated.