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New Yorker Magazine Halloween covers

The Best New Yorker Magazine Halloween Covers

Halloween has always been one of my favorite holidays. There’s something so magical about the spooky atmosphere, the fun decorations, and, of course, seeing kids get dressed up in their costumes—it’s absolutely adorable. Every year, I look forward to the creativity that Halloween brings out, from intricate pumpkin carvings to the playful costumes that fill the streets. There’s a kind of charm to this holiday that makes it feel like a celebration of both the mysterious and the joyful.

In this article, I’m diving into some of the most iconic New Yorker magazine covers that capture the spirit of Halloween. Each one brings to life the playful, eerie, and nostalgic elements of the season, much like the holiday itself. Whether it’s a cover featuring tiny trick-or-treaters or a pin up witch, these covers reflect the magic that makes Halloween such a beloved time of year. Enjoy!

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October 31, 1988 – Artist: Charles Addams
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October 31, 2022 – Artist: Sergio Garcia Sanchez
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October 27, 1945 – Artist: Edna Eicke
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November 3, 2003 – Artist: Ian Falconer
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July 8, 1961 – Artist: Charles Addams
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November 6, 2000 – Artist: Owen Smith
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October 31, 2005 – Artist: Ian Falconer
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October 31, 1970 – Artist: William Steig
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November 2, 1987 – Artist: Charles Addams
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October 31, 2011 – Artist: George Booth
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October 31, 1951 – Artist: Edna Eicke
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November 2, 1963 - Artist: Charles Addams
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October 31, 1942 – Artist: Rea Irvin
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October 28, 1967 – Artist: Abe Birnbaum
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October 29, 1984 – Artist: Arnie Levin
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October 21, 2013 – Artist: Mark Ulriksen
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November 1, 1993 – Artist: Charles Burns
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November 2, 2009 – Artist: Chris Ware
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October 28, 1961 - Artist: Anatole Kovarsky
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November 4, 1974 - Artist: James Stevenson
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October 28, 2018 - Artist: Liniers
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November 22, 1941 - Artist: Rea Irvin
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October 29, 1955 - Artist: Abe Birnbaum
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October 26, 1998 - Artist: Art Spiegelman
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October 31, 1983 - Artist: Charles Addams
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Ok - truth be told - this was never an OFFICIAL cover. It was a submitted candidate, but was rejected, I think its brilliant, though!

Did You Know?

Halloween’s Origins Go Way Back

Halloween actually started over 2,000 years ago with the ancient Celtic festival of Samhain. People believed that on October 31st (or around that time), the boundary between the living and the dead blurred, so naturally, it was the perfect night for ghosts to roam. It’s pretty cool to think that our modern Halloween comes from such a spooky, ancient tradition, right?

Celctic Samhain celebration

Trick-or-Treating Used to Be All About Poetry

Before kids were copping bags full of candy, they were going door-to-door in costume, performing poems, songs, or jokes in exchange for treats. Can you imagine? It wasn’t about the candy haul—it was more like a talent show at each door!

Vintage Halloween _1
Trick or treat! Ya dig??

Black Cats Weren’t Always Considered Spooky

Black cats might have a reputation for being unlucky these days, but in ancient Egypt, they were actually seen as symbols of good luck and were even considered sacred. It wasn’t until much later that people began associating black cats with witches and spooky vibes. I am personally sticking with the good luck reputation. I love black cats! 

Vintage Halloween _2
Another rejected New Yorker cover, but I love it!

A Very New Yorker Halloween

Halloween has always been one of my favorite times of the year. There’s something magical about the combination of spooky and playful, where ghosts and goblins walk the streets, and creativity flows through every costume and carved pumpkin. The New Yorker’s Halloween covers capture that same magic, blending humor, fear, and nostalgia into every illustration. Each one reminds us that Halloween isn’t just about scares—it’s about imagination, fun, and the community that comes together on this one spooky night.

These covers, spanning decades, show how Halloween has evolved, yet stayed true to its roots as a celebration of all things mysterious and fun. Whether it’s a hauntingly beautiful scene or a cheeky take on the season, these artists have captured the spirit of Halloween in ways that resonate year after year. As I look through these covers, it feels like revisiting the magic of Halloween all over again.

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