The Halloween holiday actually started back in ancient Celtic times as a pagan festival. A celebration known as Samhain celebrated the beginning of the dark side of the year. It was believed that the border between this world and the spirit world was very thin at this time of year which allowed the spirits to cross over from the other side. People began wearing costumes and masks to ward off the some of the evil spirits that crossed over. It became a celebration where food and drink were consumed and games were played. A form of the game of bobbing for apples survives to this day. Ancient peoples also used to put out all of the lights in their homes on this night hoping that the spirits would pass over them.
The name Halloween was adapted from the Old English term “All Hallows Even” meaning the eve of “All Saints Day” which is the day after Halloween. Starting around 1800, folks used to honor the dead or fallen by placing a candle in the window. They also carved faces of fallen warriors out of a turnip believing that the dead would still speak. As the Scottish and Irish immigrants moved to America, they discovered that the pumpkin was much easier to carve faces into than turnips and they were big enough to put candles inside, the jack-o-lantern was born.
Halloween was more of an adult holiday until activities involving children came along to make it entertaining for them like dressing up in costume. The celebrations began moving into then neighborhoods in the form of trick-or-treating. As “mischief” night became more an more popular with violence and trickery, some folks began attempting to temper down the celebration. In1920 Anoka, Minnesota had the very first Halloween parade and is known today as the “Halloween Capital of the World”.
Modern association of monsters, vampires, werewolves, etc. all came from modern movies, books, and stories to build the image of Halloween as it is known today.
Wikipedia – Halloween
“Haunted History of Halloween” – The History Channel
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