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Go Caroling Day!
When is this holiday celebrated?
Go Caroling Day is celebrated annually on December 20 every year.
Christmas Carol Day is December 19.
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What is this holiday about?
It's all about singing door to door in celebration of the Christmas Season!
This holiday celebrates carols of the past by dressing up in period costume and celebrating this holiday by going door to door singing christmas carols as a caroling group.

Definition of a Christmas Carol: A Christmas carol (also called a noël) is a carol (song or hymn) whose lyrics are on the theme of Christmas, or the winter season in general and which are traditionally sung in the period before Christmas.

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. read more about wassailing
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Origin of this Holiday
I bet the month of  December was picked because December has become a traditional time for caroling.  Why was the 20th of December picked?? Well that is the question but we think it's because the week of the 20th is the week when most organizations, clubs and church groups go caroling in communities. But unfortunately...

our research did not find the creator, or the origin of this day.
This holiday is referred to as a "National" day.  However, we did not find any congressional records or presidential proclamations for this day. Even though we didn't, this is still a holiday that is publicized to celebrate.
So have fun with it and celebrate it!

We found reference to this holiday on ECard Greeting sites
Fa la la la la la ! It's Go Caroling Day ! Time to hum all those lovely carols and welcome Christmas. Add to the joyous spirit of the season by sending our wonderful  caroling ecards to your dear ones.
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What type of holiday is this?
Weird Holiday  • United States Holiday
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Caroling Facts
The tradition of Christmas carols hails back as far as the thirteenth century, although carols were originally communal songs sung during celebrations like harvest tide as well as Christmas. It was only later that carols began to be sung in church, and to be specifically associated with Christmas.

Carols suffered a decline in popularity after the Reformation in the countries where Protestant churches gained prominence (although well-known Reformers like Martin Luther authored carols and encouraged their use in worship), but survived in rural communities until the revival of interest in carols in the 19th century. The first appearance in print of "God Rest Ye Merry, Gentlemen", "The First Noel", "I Saw Three Ships" and "Hark the Herald Angels Sing" was in Christmas Carols Ancient and Modern (1833) by William B. Sandys. Composers like Arthur Sullivan helped to repopularize the carol, and it is this period that gave rise to such favorites as "Good King Wenceslas" and "It Came Upon the Midnight Clear", a New England carol written by Edmund H. Sears and Richard S. Willis.

Today carols are regularly sung at Christian religious services . Some compositions have words which are clearly not of a religious theme, but are often still referred to as "carols". For example, the sixteenth century song "A Bone, God Wot!" appears to be a wassailing song (which is sung during drinking or while requesting ale), but is described in the British Museum's Cottonian Collection as a Christmas carol.

It is often difficult to draw a distinction between a Christmas carol and a Christmas song. To be sung by a church choir or sung in the street by amateurs, a song would have to have a fairly rapid, regular beat, which would therefore exclude a meandering crooning song such as "White Christmas". A country music song such as "Blue Christmas" might qualify, but in this case it would have to be adopted by many choirs, over many years to be truly "vernacular", and so far it has failed to gain wide acceptance. The Concise Oxford Dictionary is more generous, as it defines a carol as a "religious song...associated with Christmas".
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Other December Holidays around the world
Christmas  / National Hand Washing Awareness Week  / Relaxation Day
National Cookie Day  / National Maple Syrup Day  / Pumpkin Pie Day
National Hamburger Day  / National Candy Cane Day  / Fritters Day
Santas List Day  /  Saint Nicholas Day  / Roof over your head day
Cotton candy day  /Poinsettia Day  /Egg Nog Month  / Gone-ta-pott Day
Yule  / Make up your mind day  /
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How can I Celebrate this holiday?
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You may also be interested in these outside links:
Carols by candlelight / wikipedia Christmas Carol