The strangest Halloween cards usually depict lost or regional traditions. They’re odd because of the anachronism, not because the makers were insane (or at least they were insane for different reasons).
Most of the early cards depict fortune-telling games. These made up the main event at parties before trick-or-treating was a “thing.” My guess is that these became so popular partially because Halloween was the one time of year where it was socially acceptable to participate in “witchcraft” (of a very innocent sort) and being able to play at casting “spells.” (Whether we think of it as All Souls’ Eve or Samhain or the end of the Celtic year, the day has always been a time when you had to protect against spirits but could also play with that spooky other world in fun ways.)
For the next few posts, I’ll describe the rituals that appear on the cards and explain the source and significance. That said, it’s still more fun just to think WTF!? when you see a lady throwing an apple peel over her shoulder with the caption “Merry Halloween!”
(Other posts in this series:
Of Cabbages and, uh, Kale!

That’s not a poorly drawn vegetable costume. Cabbage and kale were a huge part of Halloween fortune-telling traditions, especially in Scotland, Ireland, and Wales. Like most of these Halloween games, the point of “kaling” was for young people to learn about their fate in love.
Robert Burns’ poem “Halloween” sums it up nicely (and you should really read the whole hilarious thing):
Then, first and foremost, through the cabbage,
Their stalks are sought at once;
They touch their own, and grasp and choose,
For very strong and straight ones.
Poor fellow Will fell off the drift,
And wander’d through the cabbage,
And pulled, for want of better shift,
A cabbage like a pig’s tail,
So bent that night. [Modern English version]

In sum: you’d run out in the field (some insist at midnight) and yank up a stalk of cabbage (Ireland), kale (Scotland), or sometimes leeks (Wales). The shape, length, and even taste of the stalk would tell you a lot about your future mate. Short and thick? Plan on cooking a lot. Withered and old? You’d probably snag a widower. You could even guess the size of your dowry (or your spouse’s wealth) by how much dirt was on the stalk. It left a lot of room for interpretation: crooked could mean deceitful, but it could also have a bit more of a literal…translation. (Miller, 38; Bannatyne, 72)

Some sources say that couples were to pull them together to find out if they were compatible. Others say it was less about the type of person you’d get but whether or not you’d be married within the year (only if your stalk come up whole rather than broken off).

When the tradition came to America, it got a bit more mischievous. On what came to be called “Cabbage Night” (or sometimes “Cabbage Stalk Night”), it was common to go out to the cabbage fields (sometimes only after crossing a graveyard to make it work) and fling the cabbage at houses. (Miller, 66) Maybe they did it after the spell, or maybe the Yanks dropped that whole bit and went straight for the vandalism. USA!

Cabbage also made it into a food-based game more common with cake but still very much part of the traditional Halloween meal: colcannon. This mix of mashed potatoes, onions, and kale would also have various tokens like a ring or coins, and, according to the particular game, if you got one of these in your portion, it would tell you how long before you could expect to be married. Apparently finding a thimble would mean you’d die a spinster. Either way, I’d fear for my teeth. (Smith)
I’ve yet to find a card with this (admittedly tasty) mush. (Yeah, I made some.) But I promise to keep looking. In the meantime, sleep on this:

One last bit: I haven’t found anything about beets or root-vegetables in particular, and the beet one’s more about how long the picker will live. Still..head out to the garden on the 31st and fortune-tell…something!


References
Bannatyne, Lesley Pratt. Halloween: An American Holiday, an American History. Gretna, LA: Pelican Publishing Co., 1990.
Morton, Lisa. Trick or treat: A history of Halloween. London: Reaktion Books, 2012.
Smith, K. Annabel. “The Halloween Tradition Best Left Dead: Kale as Matchmaker.” Smithsonian.com, 2012.
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