Halloween has its roots in an ancient Celtic festival called Samhain, celebrating the end of summer. The night marking the change of season from summer to winter, the beginning of the Celtic New Year, was supposedly filled with magic. On this day, ghosts and demons were free to roam the earth, so villagers would wear ghastly costumes to fool the spirits and make food offerings to the dead.

These pagan celebrations were adapted by the Catholic church as All Souls Day and All Saints Day. The night before All Saints Day would be called “All Hallows Eve,” then “Hallowe’en.” In the 19th century, Irish immigrants brought renewed interested in Hallowe’en to the United States, with masquerades, house-to-house visits, and the jack o’ lantern, based on a myth about a soul trapped on earth who was given the burning embers of hell to light his way.

But it was the Victorians who homogenized diverse Halloween traditions in middle-class England and America. For them, it became a genteel holiday about romance, parlour games, and child’s play. Even ghost stories were softened into tales of passion, as members of high society competed to one-up each other with their Halloween parties.

The late 1800s also marked the beginning of the “golden era” of postcards, which were the text messaging or social media of the day—people sent these cheap greetings for any reason, particularly holidays. This trend lasted until around 1918.

Turn-of-the-century Halloween postcards featured cute, fat jack o’ lanterns topped with equally adorable chubby-cheeked children. Black cats, which used to be burned at Christian festivals for being “witches familiars,” were also cuddly icons of these cards, while the witches were often depicted as very pretty ladies bringing messages of love.

The most beautiful and most collected Halloween postcards were published by John O. Winsch of New York between the years of 1911 and 1915. Winsch used heavy, rich inks and embossing on his cards, and sent them to Germany to be printed. Some appeared in sets of six, but most came in sets of four. Some of these postcards had booklets attached, and still others had die-cuts. Thanks to the Payne-Aldrich Act, which increased the tariff on imported cards, Winsch cards were two for a nickel, while cards printed in America only cost a penny.

The most collected Winsch “Hallowe’en” postcards were the artist-signed postcards designed by American artist Samuel L. Schmucker, who painted beautiful women in lush, bright colors, signing some of his artwork with the monogram “SLS.”...

The Edwardian romanticism is obvious in the accompanying verses. Winsch cards might say things like, "On Halloween, take the seeds from a Pumpkin, place them in front of the sofa in the form of a cross – then the Witches won't bother you. That's a hard name to call ma and pa but they were young themselves once and won't mind it." Or, "On Halloween, Goblins have been known to fly away with Fair Maidens. Therefore 'tis best to have some one hold you and tightly, too, -- because Goblins are strong."

One particularly popular superstition for romantic Halloween cards shows a young woman looking into a mirror at the stroke of midnight to see the face of her true love, using the light of a jack o’ lantern. At times, she is pictured looking into a hand mirror at a larger mirror over her shoulder, and other times, she is looking directly into the larger mirror, as the specter of her future husband hovers over her shoulder.

Jason Frexias, meanwhile, produced holiday cards for Winsch with round-faced toddlers with starfish hands. Because Frexias did not copyright his work, his images would be copied. An illustration of a child originally perched on a jack o’lantern would be lifted and placed on an Easter egg or a heart for a Valentine’s Day card. These knockoff illustrations, which Frexias was not paid for, lack the detail of the original. It’s particularly obvious with European holiday cards that pirated Frexias designs, where you can see the child still holding the lid of a jack o’lantern, while sitting on a flaming Valentine heart.

Ellen H. Clapsaddle, one of the most prolific American postcard artists of the era, produced some of the most collectible Halloween cards today for Raphael Tuck and Sons, International Art Publishing Company, and Wolf Publishing Company, a subsidiary of Inter-Art that Clapsaddle launched herself. Her style is distinct, particularly her illustrations of children.

H.B. Griggs is another highly collectible holiday postcard artist, although so little is known about Griggs it is unclear whether the illustrator was a man or woman. Griggs, using the signature H.B.G., published almost exclusively for Leubrie and Elkus of New York.

Grace Gebbie Drayton, known for her iconic Campbell’s Kids, made Halloween cards for Raphael Tuck and Sons showing the similar big-eyed chubby-cheeked kids. Comic-strip artist Clare Victor Dwiggins made a gorgeous set of unsigned Halloween cards in fantasy style featuring a beautiful “witching queen” presumably based on his wife, who was often a model for the lovely ladies on his cards.

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