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Go Caroling Day is celebrated annually on December 20.
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What is the definition of wassailing?
Wassailing as a practice falls into two distinct categories; the House-Visiting wassail; very much similar to caroling, is the practice of people going door-to-door singing Christmas carols. In modern times it is most commonly known through reference in various traditional Christmas carols (e.g., "Here we come a-wassailing / among the leaves so green"). And the Orchard-Visiting wassail. The term refers to the practice of singing to trees in apple orchards in cider-producing regions of England to promote a good harvest for the coming year.

Origins of wassailing
Some scholars prefer a pre-Christian explanation of the old traditional ceremony of wassailing. How far the tradition dates back is unknown but it has undeniable connections with Anglo-Saxon pagan ritual. Of recent times the word Wassail (from the Anglo-Saxon toast wæs þu hæl, "be thou hale" — i.e., "be in good health") has come to be synonymous with Christmas. The word wassail is old English (OE) and so dates from before 1066. According to the Oxford English Dictionary "waes hael" is the Middle English spelling parallel to OE "wes hal". The American Heritage Dictionary, fourth edition, gives Old Norse "ves heill" as the source of Middle English "waeshaeil".

Christmas was not celebrated anywhere before the third century, and only gradually moved northwards through Europe. Charlemagne was crowned on Christmas day 800. It was probably the Normans who brought the celebration to England. Many sources claim that William was crowned king of England on Christmas day 1066. However if you check the words of the Anglo-Saxon Chronicles (see reference below), it was described as "childer-mass day", Holy Innocents Day, or December 28. Therefore the tradition of wassailing predates the celebration of Christmas. Trolley the Wassail is celebrated on Twelfth Night January 6. However most people insist on wassailing on 'Old Twelvey Night' (January 17) as that would have been the correct date before the introduction of the Gregorian Calendar in 1752.

The practice has its roots in the middle ages as a reciprocal exchange between the feudal lords and their peasants as a form of recipient initiated charitable giving, to be distinguished from begging. This point is made in the song "Here We Come A-Wassailing", when the wassailers inform the lord of the house that

   "we are not daily beggars that beg from door to door but we are friendly neighbors whom you have seen before."

The lord of the manor would give food and drink to the peasants in exchange for their blessing and goodwill, i.e...

   "Love and joy come to you,
   And to you your wassail too;
   And God bless you and send you
   a Happy New Year"

... which would be given in the form of the song being sung. Wassailing is the background practice against which a carol such as "We Wish You a Merry Christmas" can be made sense of.

Although wassailing is often described in innocuous and sometimes nostalgic terms, the practice has not always been considered so innocent. In fact in early New England wassailing was associated with rowdy bands of young men who would enter the homes of wealthy neighbors and demand free food and drink in a trick-or-treat fashion. If the householder refused, he was usually cursed, and occasionally his house was vandalized.

The example of the exchange is seen in their demand for "figgy pudding" and "good cheer", i.e., the wassail beverage, without which the wassailers in the song will not leave, "we won't go until we've got some."

The Orchard-Visiting Wassail
In cider-producing areas of England, such as the West Country, wassailing also refers to drinking (and singing) the health of trees in the hopes that they might better thrive.

An old rhyme goes: “Wassaile the trees, that they may beare / You many a Plum and many a Peare: / For more or lesse fruits they will bring, / As you do give them Wassailing.”

The purpose of wassailing is to awake the cider apple trees and to scare away evil spirits to ensure a good harvest of fruit in the Autumn.{"England In Particular", Common Ground 2007} The ceremonies of each wassail varies from village to village but they generally all have the same core elements. A wassail King and Queen to lead the proceedings, and song and/or a processional tune to be played/sung from one orchard to the next, the wassail Queen will be lifted up into the boughs of the tree where she will place toast that has been soaked in Wassail from the Clayen Cup as a gift the tree spirits and to show them the fruits of what they created the previous year. Then an incantation is usually recited such as

Here's to thee, old apple tree, That blooms well, bears well. Hats full, caps full, Three bushel bags full, An' all under one tree. Hurrah! Hurrah!

Then the assembled crowd will sing and shout and bang drums and pots & pans and generally make a terrible racket until the gunsmen give a great final volley through the branches to make sure the work is done and then off to the next orchard. Perhaps unbeknown to the general public, this ancient English tradition is still very much thriving today. The West Country is the most famous and largest cider producing region of the country and some of the most important wassails are held annually in Carhampton (Somerset) and Whimple (Devon), both on 17 January (old Twelfth Night).

Private readings about people in Somerset in the 1800s revealed that inhabitants of Somerset practiced the old Wassailing Ceremony, singing the following lyrics after drinking the cider until they were "merry and gay:"

"Apple tree, apple tree, we all come to wassail thee, Bear this year and next year to bloom and to blow, Hat fulls, cap fulls, three cornered sack fills, Hip, Hip, Hip, hurrah, Holler biys, holler hurrah."

Wassail bowls
Wassail bowls, generally in the shape of goblets, have been preserved. The Worshipful Company of Grocers made very elaborate one in the seventeenth century, decorated with silver. It is so large that is must have passed around as a "loving cup" so that many members of the guild could drink from it. There are surviving examples of "puzzle wassail bowls", with many spouts. As you attempt to drink from one of the spouts, you are drenched from another spout. The drink was either punch, mulled wine or spicy ale.

See also resource links:
Apple Wassail: The Apple Wassail is a traditional form of wassailing practiced in the cider orchards of South West England during the winter. There are many well recorded instances of the Apple Wassail in the early modern period.
resource /documentation_license
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Wassailing!