OyChicago blog

Ah, the fall season—leaves changing to colors of the rainbow, the air getting brisk and windy—and, of course, Halloween! There is no other national holiday where adults and children can dress up for one day and just have fun. Of course, we Jews have Purim in the spring, filled with delicious hamentaschen, noisy graggers and of course, killer royalty costumes. So, in the spirit of the ghoulish holiday, I thought I’d reminisce on some of my fondest memories trick or treating and share some special moments I had with my two younger siblings.

As early as I can remember, I have dressed up for Halloween. I know this because my own mother won’t let me forget it, having photo albums detailing all of the awesome and decorative costumes my brother, sister and I used to wear. Lucky for us, despite growing up in the city, we lived in a condo building as well as on a block that was very kid-friendly for trick or treating, but it was not until my brother and I were around 10 that we were allowed to venture off on our own—together, of course—and see what trouble we could cause. Because my brother Jesse and I were so close in age, a lot of our costumes would either match or complement each other. For example, one year my brother and I had Teenage Mutant Ninja Turtles body suits / pajamas with masks and turtle shell candy bags. I was blue-colored Leonardo, the leader with the katana, my brother was yellow-colored Michelangelo with the nun chucks.

Back then, my sister was too young to go out with us, so while we went out candy-hunting she would help my parents pass out candy to other trick or treaters. Another year I dressed as Dick Tracy, to the nines! I donned the yellow suit, threw on the fedora cap, and wielded the toughest looking plastic tommy gun anyone could imagine. Pretty soon, my brother and I were the talk of the condo, setting the Halloween trends and always garnering the most attention, and therefore the most candy. Rain or snow, windy or cold, my brother and I braved the elements and triumphed like pirates after a hearty pillage. In the later years, our little sister Hayley would join us, inevitably in some royal or fairy type costume, on our annual candy hunt. It really was a great way for all three of us to grow closer and share an activity that all of us enjoyed.

After we’d return from our expeditions, Jesse and I would come back to the dining room table and dump everything out, immediately scoping out our favorites. Since we knew each other so well and which particular candies and sweets we each liked, we began the process of dividing everything up. I scrambled to snatch up all the Dots, Reese’s and Krackel/Hershey I could get my hands on, while Jesse went straight for the Pixie sticks, Gummy worms and Smarties. On occasion, we would come across a candy we’d never seen or heard of before (most likely from one of the houses that might be a little too old to know what treats young children like, if you catch my drift). When that would happen, guess where it went? Our little sister Hayley’s pile. This way, we never seemed neglectful or dismissive of our youngest sibling, and the candy we didn’t want was technically not going to waste (right?). After what seemed like hours of sorting, we finally had our candies all organized and lined up on the tabletop, which of course was followed by ravenous devouring and then extreme aching of the stomach.

As we got older, we still found ways to stay involved in the trick or treating festivities and dress up in something cool. I happened to find my way to the University of Wisconsin where Halloween was a sacred and timeless celebration amongst the students. While those parties were fun and festive (and a little out of control), I will always remember the good times I had trick or treating back home, from sloshing around in the rain in my ninja costume to divvying up the candy with my siblings. I will always have fond memories and hope to make more each and every October.

Speaking of having fun for Halloween, this year, if you are looking to have some fun and celebrate Halloween with a multitude of young, energetic Jewish partygoers, my close friends Brad and Brandon of Juicebox Promotions are throwing their annual shindig at Enclave. Tickets are cheap now so grab them and secure your night of fun and costume mayhem now: http://enclavechicago.com/horror/ These guys also throw other fun and festive seasonal bashes that do attract a large and rather young Jewish crowd, so don’t be shy and mingle and schmooze the night away this coming Halloween.

So, what are you going to be for Halloween?? I hope to see many of you out there in your costumes, or better yet, send Oy!Chicago some pictures of your wacky adventures and we will see who has the best costume!

L’Chaim!