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The 8 Holiday Books That Deserve to Be Annual Traditions

Andrea Wright by Andrea Wright
November 12, 2025
Reading Time: 4 mins read
The 8 Holiday Books That Deserve to Be Annual Traditions

Image Credit: Freepik

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The perfect holiday duo? Cocoa and a good book. Some books aren’t just for reading once. In fact, they can become a part of the season itself. These eight holiday books capture the spirit of the season so well they’re worth revisiting year after year.

8. The Greatest Gift by Philip Van Doren Stern

The Greatest Gift by Philip Van Doren Stern
Image Credit: Reddit

What if you could see the world as if you’d never existed? That question was first asked in a short story born from a dream. Author Philip Van Doren Stern wrote “The Greatest Gift” in 1943 but couldn’t find a publisher. So he printed 200 copies and sent them to friends as a 21-page Christmas card. The story is a reminder that our lives matter in ways we may never fully appreciate.

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7. Rudolph the Red-Nosed Reindeer by Robert L. May

Rudolph the Red Nosed Reindeer by Robert L. May
Image Credit: Reddit

In 1939, Montgomery Ward tasked Robert L. May with creating a character for a free holiday booklet to attract shoppers. Drawing inspiration from his own childhood insecurities and the “ugly duckling” story, May created Rudolph, a misfit reindeer. The company gave away over two million copies that year. The story of embracing what makes us different resonated so deeply it became a cultural phenomenon.

6. The Velveteen Rabbit by Margery Williams

The Velveteen Rabbit by Margery Williams
Image Credit: Reddit

“What is REAL?” asks the Velveteen Rabbit in this 1922 classic. The answer he gets from the wise old Skin Horse, that you become Real through being loved, is a profound lesson on vulnerability and authenticity. Rereading this at different stages of life can offer new layers of meaning and remind us that being loved, and loving in return, can be transformative.

5. The Polar Express by Chris Van Allsburg

The Polar Express by Chris Van Allsburg
Image Credit: Amazon

This story is about a boy who boards a mysterious train to the North Pole. Van Allsburg’s beautiful illustrations create an atmosphere of magic, but the book’s true power lies in its message: that the most important things in life are often the ones we can’t see. An annual reading keeps your sense of wonder alive and will remind you that “seeing isn’t always believing.”

4. How the Grinch Stole Christmas! by Dr. Seuss

How the Grinch Stole Christmas! by Dr. Seuss
Image Credit: Amazon

This 1957 classic is a witty critique of holiday commercialism. The Grinch believes he can stop Christmas from coming by stealing all the presents and decorations from Whoville. However, he discovered people are still celebrating, their joy coming from community and spirit. An annual reread helps us to look past the material trappings of the holiday season.

3. The Gift of the Magi by O. Henry

The Gift of the Magi by O. Henry
Image Credit: Amazon

This short story is about an impoverished couple, Della and Jim, each selling their most prized possession to buy a Christmas gift for the other. Their gifts were useless, but their actions revealed a love that’s more valuable than any possession. This story can be a powerful antidote for a world obsessed with finding the “perfect” gift.

2. A Visit from St. Nicholas by Clement Clarke Moore

A Visit from St. Nicholas by Clement Clarke Moore
Image Credit: Amazon

“A Visit from St. Nicholas” (now known as “’Twas the Night Before Christmas”) was first published anonymously in a newspaper. It transformed the image of St. Nicholas from a stern figure into the jolly, reindeer-driving gift-giver we know today. Rereading it is like plugging into the source code of the American Christmas tradition.

1. A Christmas Carol by Charles Dickens

A Christmas Carol by Charles Dickens
Image Credit: Amazon

Charles Dickens wrote A Christmas Carol, driven by a desire to address the deep social inequalities of Victorian England. It’s a ghost story, a social protest, and a tale of redemption all in one. An annual reading offers a chance for us to confront our own potential for greed and isolation, but it can also affirm our capacity for empathy and second chances.

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