Spooky Season’s Greetings from Chicago’s Past

Although Halloween is annually observed on October 31st, the celebration of all things scary and supernatural now bleeds into the entire month of October. This extended practice of Halloween festivities has led the month to now affectionately be known as Spooky Season.

I particularly love when people embrace the true Halloween essence of darkness and gloominess by dressing up in spooky costumes, telling scary stories around the campfire, reading and watching haunting stories on the big screen, and setting up decorations that are to die for. These frighteningly good spirits greet us from Chicago’s past with photos from the Chicago Park District Records: Photographs Collection found in our digital collections.

When it comes to the toddlers and babies, it is best to keep their first time being introduced to Halloween’s spookiness as lighthearted as possible. In this photo at Humboldt Park, a child poses with a smiling pumpkin carving and a black kitten. By the look on the kid’s face, that still might have been too scary! But you can never completely strip away the Halloween holiday’s unnerving essence.

As kids get older, they learn that with Halloween there is a sense of delight that goes hand in hand with the macabre. In this photo at Riis Park, the little girl is smiling at what would be a horrifying sight outside of the festive season.

Halloween has come to be embraced and celebrated as a way of finding comfort in facing the spookiness and horrors that are too much to bear alone. It is a time to transform something grim into something pleasantly haunting. Surrounded by loved ones, you learn to face and walk with your inner demons instead of running away from them.

By the time kids reach their pre-teen and teen years they are able to more maturely balance and distinguish the dark topics. In this photo at Hiawatha Park, there are no smiling faces among the makeshift graveyard, but that is no indication the kids aren’t having a killer time – it's actually quite the opposite!

Having a childhood filled with endearingly scary Halloween memories turns kids into adults who can find the humor in life, even when it’s a frightening time. In this photo at Mount Greenwood Park, adults show you that you are never too old for a fun scare.

Spooky Season is a space and time to find comfort and humor in topics that are too dark and horrifying almost any other time of the year. This doesn’t take away from the heaviness and seriousness of these topics. It just gives space to come together in community to find the lightheartedness in the dark.

Such a screamin’ good time with family, friends, and neighbors is too much for one day to contain, so now a lot of people find excitement in celebrating Halloween festivities for the entire month of October.

If you want to see more past Halloween fun throughout the city of Chicago’s Parks, check out the Chicago Park District Records: Photographs Collection or explore our other digital collections.