How Holiday Treats Can Trick Us

Halloween has always been my favorite holiday. But, like any holiday, the very anticipation that makes it a treat can also trick us.

One memorable Halloween night I was lucky enough to have a ticket for Richard Crowe’s sold-out Supernatural Tour, which combined visits to some of Chicago’s most notoriously historic spots with tales of the spirits who remained.

As our bus entered the Englewood neighborhood, Crowe recounted a  macabre tale so wickedly good that I was surprised I’d never heard it before. In the late 1800s, H. H. Holmes designed the building that stood on the corner of 63rd and Wallace, the one that neighbors referred to as “The Castle.”


The Castle, a.k.a. the World’s Fair Hotel, was situated to attract out-of-town visitors to the Columbian Exposition of 1893.

Today, that hotel is remembered by another name, Murder Castle, because, thanks to Holmes, America’s first serial killer, several of its lodgers were never heard from again.

Crowe’s tale of this killer’s exploits led us to the eerie, lagoon side of one of my childhood haunts, The Museum of Science and Industry. It’s the last landmark standing from that famous, and, for tonight, infamous World’s Fair. I’d never seen the mysterious figure dressed in clothing from a bygone era who walked the Yesterday’s Main Street exhibit after closing hours, but based on the accounts of several night watchmen over the years, Crowe suggested that old H. H. may have taken up residence in these familiar surroundings after his death by execution in 1896.

The chill I felt was both literal and figurative as we got out of the bus and stood watching the rats swimming in the lagoon. When a light rain entered the mix, many of us opted for the shelter of the tour bus to whisk us to our next point of interest, Resurrection Cemetery. But, shouts of excitement soon arose from those who had lingered. Someone returned to the bus to alert us that there was a ghost in back of the museum.

As I rejoined my fellow ghost busters, sure enough, there it was. Across the rat-filled lagoon, standing among the concrete Greek maiden columns who raised the roof, stood a figure in an ancient frock coat. The apparition wasn’t transparent, it was likely flesh and blood. Several folks called out “Happy Halloween, H.H.,” but it just stood there, unmoving.

Crowe seemed just as surprised as the rest of us. He assured us that the figure wasn’t “a plant” he had paid a few bucks to give us a cheap thrill. A likely explanation was that it was some homeless person settling in for the night, every bit as surprised to see us.

If forced to choose a favorite Halloween, that one will do, but there have been several strong contenders both before and since.

For several Halloweens, I’ve attended live performances by the Willamette Radio Workshop at the Kennedy School, a local grammar school converted into a brewpub/hotel. This year, E. was taking a few days off to enjoy some fall color walks and hikes, so I suggested it might be something we could do together.

Past performances by the Workshop have included memorable renditions of Frankenstein, Dracula, War of the Worlds, and other spooky tales. It’s always fun, and since the school is a popular Trick or Treat destination, it’s an easy, low-key way to see what costumes are popular. Oh, and since it’s a brewpub, there’s beer available.

On Halloween morning, I checked for the performance times on the  newly-redesigned Kennedy School website, but there was no listing for the event. I hadn’t actually confirmed that they would be performing, I had just assumed. Oh, well.

On the one hand, I was disappointed that I would be missing out on this minor Halloween tradition. On the other, it gave me the chance to think about what factors led to that disappointment, and lead to more serious feelings of holiday depression.

The New Oxford Dictionary that comes with my computer defines happy as feeling or showing pleasure or contentment.

Margaret Paul, Ph.D. uses the word happiness instead of contentment in her essay “The Difference Between Happiness and Pleasure,” but she gets at the conflict between the two ideas.

“There is a huge difference between happiness and pleasure. Pleasure is a momentary feeling that comes from something external — a good meal, our stocks going up, making love and so on. Pleasure has to do with the positive experiences of our senses, and with good things happening. Pleasurable experiences can give us momentary feelings of happiness, but this happiness does not last long because it is dependent upon external events and experiences. We have to keep on having the good experiences — more food, more drugs or alcohol, more money, more sex, more things — in order to feel pleasure. As a result, many people become addicted to these external experiences, needing more and more to feel a short-lived feeling of happiness.”

Halloween gives us many short-lived feelings of happiness. The conditioning starts young with the amazing concept that on this one day of the year, you can put on a costume, and basically extort candy from friends and neighbors with the magic words “Trick or treat.”

After graduating from trick or treating, there are frequently Halloween parties to attend, or haunted houses. Then you can graduate to less-exciting but still fun exercises like taking ghost tours or live stories presented at your local brewpub.

Each year, all the sensory cues to trigger those pleasant holiday memories are in the air. The turning leaves mingle with Halloween decorations. All the stores put out big Halloween displays. And our memories can be highly selective. And, if you still watch The Simpsons, there’s the Halloween episode.

But, how pleasant was it? How happy was I? Come to think of it, a lot of the Halloween candy wasn’t really that good. Depending on the costume I war, I was often too hot or too cold. If there was a mask involved, it was hard to see.

The Halloween parties I attended were like any other parties. They weren’t especially fun.

The haunted houses were usually kind of lame.

The ghost tours I took were fun, but some were kind of pricey.

And in that moment of truth that comes around each year when I have to decide what to do for Halloween, I face that moment where I’m prompted to set aside my contentment in order to seek pleasure.

Stephen Tobolowsky’s monologue “Sex, Death and Halloween” sums up a certain paradox about holiday depression better than I ever could. “No matter where you go, no matter what you do on Halloween, you will always imagine somebody else is having more fun than you are.

Author: Bruce Cantwell

Writer, journalist and long-time mindfulness practitioner.