No matter what, it happens every October. This is when I am guaranteed a few restless nights. Evenings when I toss and turn, when my mind twirls and whirls, when I glance at the clock every hour until the first morning’s light. No matter how much thought I’ve already put into it, or how much I’ve prepared, I experience this phenomenon. The reason? It’s all because of Stingy Jack.
As the 18th century legend goes, this tippling trickster from Dublin spent a lifetime cheating the devil with his cunning schemes just to make a few farthings. However, upon his death, the joke was on him. It’s then his deceitful gig was up and because of his evil deeds St. Peter denied Stingy Jack entrance to Heaven and Satan would not let him into Hell. So Stingy Jack was sentenced to roam the Earth for all of eternity with only a carved turnip and coal to light his way.
And…when Stingy Jack died, Jack of the Lantern was born. Over time, Jack of the Lantern became Jack-o-Lantern, what we commonly know as a carved-out pumpkin lit like a lantern. Credit for creating this custom goes to the Irish and Scottish. Around this time every year, they whittled scary faces into root vegetables such as turnips, beets, or potatoes and illuminated them with candles. Placed in windows and on doorsteps their purpose was to ward off Stingy Jack and evil spirits on All Hallow’s Eve. Here in the U.S., we commonly carve pumpkins for our Halloween displays.
So, what does any of this have to do with my sleepless October nights? For as long as I can remember, I’ve taken the time to carefully consider how to customize my pumpkins for Halloween. Decades of carving squashes with whimsical and friendly faces, has left me, how shall I say it, a little…bored. But, once I put down my knife, and I picked up my art supplies, a whole new world of delightful decorating designs opened up to me!
While more challenging than simply cutting shapes into a fleshy gourd, now I get to be a little more creative. I’ve painted, zentangled, bejeweled, collaged, stickered, pom-pommed, and glued materials to my little pretties! Some of my past favorites include a spooky Poe-esque raven, a 60s hippie dippie creation in neon colors, and perhaps my favorite to date, two small pumpkins painted like donuts with glued sprinkles on top! I even bought a pink bakery box to display them in.
From my journal: October 3, 2025, Newbury Park, California
“…maybe a pumpkin with painted positive words? Black stitching, white words, a floral, my usual zentangle?”
Each year I am inspired by something I’ve seen, heard, or am feeling and this October has been no exception. With the news as of late, I decided one of my creations would be a positivity pumpkin. Painted in cheerful greens, with tiny red, orange, blue, and yellow flowers, and the words CHOOSE HAPPY on it, just looking at it makes me smile. A unique floral pattern and a new zentangle design embellish my other two. Now completed, I can rest easy, at least for another eleven months before visions of pumpkins will begin to dance in my head, and my thoughts will once again return to…Stingy Jack.
But for now, have a Boo-tiful Halloween and Best Witches for a Spooktacular celebration!
A Journal Journey 