Motherhood
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How Do You Celebrate Halloween?

By: Jen Shoop

I’m guessing some Magpies will agree that the best parts of Halloween have little to do with watching our kids dress up and trick-or-treat (and nothing to do with all the mediocre-to-bad candy they hoard). Don’t get me wrong — I love their excitement. I have the fondest memories of Hill toddling behind his sister, not fully comprehending the holiday, and placing his own candy in the outstretched baskets at various homes we’d visited. I adore their mounting energy as they put on their costumes, chomping at the bit to get outside, and their shrieking, unbridled joy as they sprint around in the dark with bags full of candy well past bedtime. Landon and I often lock eyes over their heads in shared appreciation of their wound-up delight.

But what I really love is my neighborhood on Halloween. We gather in our cul de sac, order a couple of pizzas, open some wine, and hang out while the kids run amok. In years past, we’ve held informal “parades” where the kids march around in their costumes at a designated time before we turn them all free to trick or treat, but we might have aged out of that tradition as of 2026, with most of the kids well into elementary school and several in middle school. This imminent shift leaves me a tiny bit blue, but mainly grateful that we’ve been around long enough to observe a change-of-guard. Welcome inconvenience, as we say. After all, what a privilege, to watch your children outgrow something.

Every year, while I am standing in my cul de sac on Halloween, I find myself zooming out and thinking: how charming, how village-like, that we celebrate this way. Just a bunch of good-natured neighbors standing around in the October air, indulging in the season, stewarding the joy of the neighborhood’s children. It feels somehow primordial. As if we are participating in some age-old impulse to gather and toast the turn of the year and raise our kids together. And while the candy gathering is ostensibly the diadem of the day for my kids right now, I have a hunch that they will look back on Halloween as adults and consider the “neighborhood party” as they call it the happiest and coziest high point of the holiday. I can almost feel the nostalgia laying its roots.

A couple of un-aesthetic photos from this special tradition over the years below. I look at these and feel warm all over.

halloween parade

What specific Halloween traditions do you look forward to every year? Could be anything! Could be the chili you make for post-trick-or-treat dinner, or kitting out your front porch! (Growing up, my favorite part of Halloween was sorting candy on the rug of our family room in front of the crackling fire while my Dad read “The Tell-Tale Heart”!)

Please share!

A Couple of Gilt Halloween Memories…

While I was looking for pictures of our cul de sac magic, I came across so many photos of Halloween pasts, and all of them reminded me of how narrow and specific the special memories are.

In the first photo, I took Emory to a playground on Halloween when she was 1.5, all dressed up, just the two of us. I was newly pregnant with Hill. We weren’t meeting anyone; she was cute as a button dressed up as a bee and I can still remember the exact playground, the chill in the air, the way she reached for me. (Also, sigh, the days she let me put a bow in her hair!)

In the second photo, Landon and I inflated spider balloons and left a scavenger hunt of mini pumpkins all over our New York City living room. This was COVID and we had to create the magic in minute ways. I will never forget their joy when they ran out of their rooms in the morning! (You can get similar balloons here and here — or these cute ghosts!!).

The third is an iconic moment of forcing your kids to pose by pumpkins. Why do we do this? My candids and spontaneous action shots invariably turn out better. Hill’s look of exasperation (note the Hot Wheels in his tiny fist a propos of this post) and Emory’s air of distraction are perfect.

In the fourth image, we took Emory trick-or-treating on the UWS as Cinderella in her hilarious hoop skirt costume. She went trick or treating at the dry cleaners, the grocery store, the front desks of a couple apartment buildings! Everyone got in on the fun. Life as a New York baby!

Post-Scripts.

+Magpies share their favorite offbeat seasonal rituals.

+Great picks for family movie night.

+The magic of childhood meals.

Shopping Break.

+Transfixed by these idea of this sweater with a classic jean like this.

+These new $60 Quince pants are so fab! I love the idea of them with a cashmere turtleneck in navy or brown.

+This Farm Rio dress stopped me in my tracks.

+I ordered some of this bone broth hot cocoa to try! Candidly, heard mixed reviews from Magpies — will report back with thoughts. Some of you said it tasted too sweet; others say you love it as a nighttime no-guilt indulgence. I also ordered some of this Mexican hot cocoa from Spice House!

+We have an enamel milk warmer like this that I’ll use to heat milk for the cocoas, and then froth with this.

+Everyone should have one brightly-colored beanie to zhush her fall-to-winter wardrobe! I just got the peony pink.

+Thinking ahead: what to wear all Thanksgiving week, especially while shopping Black Friday.

+Still my favorite undereye concealer ever. Does not settle into fine lines, blends beautifully. JUST THE BEST.

+50% off at Lands End with code PUMPKIN. I really love their flannel sheets. I thought I’d hate them (too hot) but they are the ultimate cozy soft landing in winter, when I am forever freezing. The cypress green plaid or this gingham would be charming right now — fall cabin vibes! — but of course the tartan would be lovely for holiday. So, so soft. They also have cute holiday sheets for little kids’ beds. Finally, these canvas bins are endlessly useful — a home for loose shoes, a tote for travel, a station for stuffies and blankets, etc!

+Venus Williams just launched a tennis-oriented collab with Crate +Barrel kids and the collection is super cute!!! Love this tennis ball storage bin, these sheets, this swivel chair, and especially these clever sports ball holders! The latter would be amazing room decor but also practical for storage in a mud room or garage!

+While you’re there, snag some of these personalized kids Christmas sacks. A good way to keep bigger gifts or gifts in odd shapes covered, and then kids can use them to gather their gifts and bring upstairs. And, of course, love that they are reusable.

+My new cozy bedroom / getting ready slippers.

+You loved these little lunchbox notes I shared last week! I tuck one into my kids’ lunch every day! Other Etsy finds I love: these personalized notepads (I live for a notepad), this brass door knocker, and these personalized knit hats!

This post may contain affiliate links. If you make a purchase through the links above, I may receive compensation.

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