Trick-Or-Treating Traditions

On a scale of 1 to 10, how much do you love Halloween? I told the other #hustlemoms I’d write something this month so I’ve been thinking about what to write about and how I felt about Halloween for a few weeks now. If you had to guess, whether or not I’d be into Halloween, what would you say? If you guessed “she’s not that into it”, you’re right. 

Don’t get me wrong, I don’t dislike Halloween, nor do I have a problem with anyone who LOOOOVES Halloween; it’s just not me. I don’t do scary and the whole costume thing just gives me anxiety. There are parts of Halloween I do like, especially the candy. After giving it some thought, I’d have to say that what I like about Halloween is a combination of nostalgic feelings of Halloween from my childhood, and the tradition of what Halloween has been for my kids. 

So this sounds really weird – part of what I like about Halloween is largely positive feelings about Halloween growing up; except I really don’t remember details. I guess that’s a good thing — big picture recall = Halloween = Good, but I don’t have vivid memories of why. I can’t remember any of my costumes other than two or three years I remember wearing my dance recital costumes to the Halloween parties at school, but there’s no way I’d be able to wear those out for trick-or treating. If anyone has any memories of any of my costumes, please fill me in. I remember being a blue M&M when I was 16, but that’s it. I think it’s odd that I don’t remember any of my costumes….but what DO I remember? 

Trick or treating started as soon as we got home from school and lasted all night. Probably like 3:30 to 8. I absolutely hate that trick or treating is so regulated now and limited to 2 hours. The best part of trick or treating as a kid was how much candy you could get and how much stamina you had running house to house, and how to balance returning home to empty your bag of candy at the right time so you weren’t slowed down by a big bag that got too heavy. I remember the Halloweens that were rainy and the ones where there was snow. I know there must have been one or two Halloweens where it was warm, but I definitely remember the years with rain and snow, and not letting that slow us down. 

Who’s us? Me and my brother Bobby most years. We’d race each other house to house with my Dad watching from the sidewalk until we were old enough to go on our own. My Dad hates to be cold, but he was the one to take us trick or treating while my mom passed out candy from our house. Once my Dad got too cold or me and Bobby got too tired, we’d go home, dump out all our candy from pillowcases, wait patiently while my Mom looked through the candy for razor blades or drugs or who knows what, and then it would be time to start the organizing and trading. Back then, we each had to donate some of our Butterfingers to my Dad. Over time that changed to Kit Kats. For my Mom, it was always Snickers. Once we paid our “tolls” that’s when we started with the trading. I hardly remember what Bobby liked that I was willing to part with, but I remember the negotiating. 

My fondest memory was Halloween 1993, when October 31 fell on a Sunday. In the south suburbs of Chicago, certain cities didn’t want to have trick or treating on a Sunday and some cities didn’t care. Halloween 1993, was the bestest ever because we got to go trick-or-treating two days in a row; one day by our house and the other day at my cousin Josh’s house, who lived in the town next to ours. 

There was no trick-or-treating in my life from 1996 when I got “too old” to go door to door, until 2001 when my Dad and I took Oscar trick or treating to a few select neighbors houses. His first Halloween, he was six months old and he wore a fuzzy bumblebee costume. Rinse and repeat for 2002, my Dad and I took Oscar trick or treating when he was dressed as a samurai warrior. 2003, my Dad and I took Oscar trick or treating when he was dressed as Thomas the Train. In subsequent years, Oscar was a Power Ranger, and then every year after that he was a Star Wars character or a football player. The costumes changed every year, but there were a few constants — we went trick-or-treating every year with my Dad, while my Mom stayed back at the house, passing out candy. My Grandma Lorraine joined us at my parents’ house every year to pass out candy and look at all the kids’ costumes. And every year my parents ordered Popeyes Chicken because it was my Grandma’s favorite. Once Mikey was born, he joined in on the trick-or treating traditions, and so did Scarlett, and so did Isabella. 

Since the little kids have been born, we’ve done a few other Halloween events, like costume parades, trunk or treats, track or treats, etc. but the number one constant is going trick-or-treating at Grandma and Grandpa’s house. That’s a tradition we won’t stop. When I think of Halloween, it all comes down to trick-or-treating with Grandpa and helping Grandma pass out candy to the kids and going through and admiring all the candy you got. My kiddos know that Mommy’s favorite is Milky Ways and they have to set aside some Snickers, Reese’s and Twix bars too. Fingers crossed for a warm and safe Halloween this year. My kids’ costumes are so cute and I’ll share pictures next week! 


Katie Helgesen

Katie Helgesen is the Senior Director of Business Intelligence at Dealer Inspire, a fast-growing and award winning technology company near Chicago. Katie and her husband, Todd, have 4 awesome kids and love living in a small community centered on a lake in northwest Indiana. Baseball, t-ball, and soccer schedules are just a few pieces of Katie’s Mom Hustle. Her daydreams revolve around finding more “me time” and traveling. In real life, Katie keeps herself sane with naps, Netflix and eating out as often as she can.