Halloween Nostalgia: How the Grace Community Remembers and Celebrates the Spooky Season!

Media provided by Colin Todd, Chair of Grace’s Visual Arts Department and Dean of Class of 2028

As October 31st approaches, the Grace community is feeling nostalgic for their childhood Halloween memories. From favorite costumes to funny mishaps, students and faculty alike are sharing how they’ll celebrate the spooky season this year—and remembering what Halloween once meant to them.

Halloween in New York is now in full swing. East Village brownstones are strung with cobwebs, and expressive skeletons sway from the trees. A massive Spirit Halloween store has just opened on 14th Street and 6th Avenue. Coffee shops’ menus have been updated with delicious pumpkin chais and mouth-watering lattes. (Check out Luckin’ coffee for cheap and tasty beverages, or Starbucks for their classic pumpkin spice latte!)

Amidst all this October excitement, Grace community members take a moment to reminisce on the place Halloween holds in their childhood memories. For a young Andrew K. ‘26, the holiday meant “getting stuffed to the brim with orange oreos by my grandma.” Halloween was “swindling young children into giving me more candy,” joked Sylvie P. ‘27. For Dana Foote, Halloween evokes memories of “going around the neighborhood with rolls of toilet paper and TPing trees and houses.”🧻 For some other members of the Grace community, Halloween was a highlight of the year.

Mr. Todd, Chair of Grace’s Visual Arts Department and Dean of the Class of 2028, vividly recalled his favorite Halloween memory: “I was maybe eight or nine. I remember getting a whole kit of fake skin and makeup and making my own monster face–it looked really gross and disgusting. It really freaked people out,” he said with a grin. This year, he is going as Vecna from Stranger Things and trick-or-treating with his daughters, who are dressing up as Wednesday Adams and Red from Descendants.

Sylvie P. ‘27 also has a distinctive Halloween tradition. “My family has a place out on the North Fork called Orient,” she said. “The interesting thing about Orient is that they do Halloween early, so I always had two Halloweens. Other than us being 8-10 year olds, going feral in rural cornfields, we’d do candy trading where we traded and pawned off candy. We’d get into fights. Things would be thrown.” This year, Sylvie is going as Princess Diana and looks forward to handing out candy to young trick-or-treaters.

Sophie L. ‘28 is also familiar with costuming as Halloween royalty: “I got so many compliments — in kindergarten I was the Queen of Hearts for Halloween,” she said. “This year, I’m going to be a Fairy because I always wanted to be a fairy once I turned 16.” 👑🧚 

However, Halloween isn’t everybody’s cauldron of tea. “To be brutally honest, I don’t love Halloween,” admitted Ms. Campbell, Director of Admissions at the High School. She remembered the year she dressed up as Tony the Tiger, the brand ambassador of Frosted Flakes cereal: “That year was the first time we were allowed to go [trick-or-treating] alone, and it was scary. I remember fear. But I also remember my great tiger costume.”

Dana Foote agreed: “I was always someone who didn’t like Halloween, though I love pumpkins. It would always scare me and creep me out. I would just want to run home but I tried to be brave.” Now, despite her childhood distaste, Dana now finds her October’s consumed by Halloween planning. “Cut to having kids— Halloween is a huge deal, and I got really into dressing them up. And here at Grace, I coordinate the faculty Halloween costume.” 

With a suspenseful drumroll, she revealed:

This year’s faculty Halloween costume is WICKED!!!!!!

Her two god-children, both Grace lower schoolers, are also going as Wicked characters, and Dana herself is going as the Wicked Witch/Elphaba. It seems like the spooky spirit has found Dana after all!

With Halloween falling on a Friday this year, Grace students are making exciting plans for “Halloweekend.” Phoenix B. ‘29 is planning to go to a party as a vampire and Souja Boy. Andrew K. ‘26 might attend NYC’s annual Halloween parade, and has three costumes in the works: a sailor, Donald Duck, and 2015-era Justin Bieber. Bo N. ‘26, like most seniors submitting Early Decision to colleges, will be spending Halloween night finishing his apps— then celebrating afterward.

While not everyone loves Halloween, it remains a festive, fun, and unforgettable holiday. Whether you have five different costumes planned or you dig out the same witch-hat every year, Halloween — especially in New York City — is always an experience to remember. 

So, what will you be this year? A superhero or a sitcom character? Will you go trick-or-treating on the brownstones of 11th street or in Upper West Side apartment buildings? No matter how you spend your Halloween, this holiday will ensure you find fun on every cobwebbed corner and down every spooky street.

Happy Halloween!!!

Caitlin L. ’27, the author, is a staff writer for The Grace Gazette.