80+ Brilliant Caldecott Award-Winning Children’s Books

80+ Brilliant Caldecott Award-Winning Children's Books 

If you don’t know where to start building a beautiful library of books for the loved little ones in your life, start with Caldecott award-winning children’s books. When you see a Caldecott medal shining off the cover of a book, you know it’ll be a good read. Moreover, that book will have brilliant illustrations.

What are Caldecott award-winning Children’s books?

Each year, the Caldecott Medal is awarded to an artist of an outstanding children’s picture book. The Caldecott Medal, named for children’s illustrator Randolph Caldecott, was created in 1937 and honors “the most distinguished American Picture Book for Children published in the United States during the preceding year,” according to the American Library Association.

Who won the first Caldecott Award?

Jim Razzi and Fred Marvin’s Snow-White and the Seven Dwarfs won the first Caldecott Award.

Caldecott award is such a great indicator of quality children’s books. As you know, illustrations are such an important part of children’s books, and the power of illustration is strong. They help the story come alive by giving the reader a clear visual of what is happening in the story. Good illustrations can spark the imagination and encourage the reader to think deeper and more creatively.

Many of my favorite children’s books are Caldecott award-winning children’s books, and I want to curate the whole Caldecott winner children’s books with you. And if you’re looking for an award-winning title for your child’s home library, check out this list of classic and new Caldecott award-winning children’s books.

“This updated version of the Caldecott-winning classic by illustrator David Small and author Judith St. George includes our forty-second president, George W. Bush, as well as new illustrations. There are now three Georges in the presidential name catalog, a Bush beside the presidential family tree, and a new face on the endpaper portraiture.
This St. George celebration, illustrated by Small, depicts the foibles, quirks, and humanity of forty-two men who have risen to one of the world’s most powerful positions. This is ideal for this election year—and every year!”

Trouble could be close behind when a tiny fish appears wearing a round blue topper (which happens to fit him perfectly). So it’s a good thing those massive fish won’t wake up. And even if he does, it’s unlikely he’ll remember what happened… As the best-selling book, visual humor swims to the fore. Jon Klassen follows up his critically acclaimed debut with another deadpan-funny story.

This New York Times Bestseller and New York Times Best Illustrated Book tells a love and loss story as only Chris Rashcka can. Daisy’s anguish when a larger dog destroys her favorite ball will be understood by any child who has ever had a beloved toy break. Caldecott Medalist Chris Raschka explores the joy and sadness that having a special toy can bring in pictures, following in the footsteps of his nearly wordless picture book Yo! Yes? Raschka’s signature swirling, impressionistic illustrations, as well as his affectionate story, will appeal especially to young dog lovers, teachers, and parents who have children who are grieving the loss of something special.

This beautiful picture book debut includes The Best Sick Day Ever and the zoo’s animals. Friends come in a wide variety of forms and dimensions. In the case of Amos McGee, numerous species as well! He spends some time each day with each of his buddies at the zoo, running races with the tortoise, entertaining the timid penguin, and even giving the owl bedtime stories. However, when Amos becomes too ill to travel to the zoo, his animal companions realize it’s time they gave back.

“This Caldecott Medal-winning tale of a mouse that turns into a tiger is a retelling of an Indian fable from the Hitopadesa by Marcia Brown.

A loving hermit uses magic to transform a little mouse into a cat, a dog, and a majestic tiger when he is in danger from big jungle predators. But he must pay the price when the haughty tiger forgets his modest beginnings and acts ungratefully. This Indian legend is brought to life by Marcia Brown’s enchanted woodcuts with the same expertise that earned her a second Caldecott Medal.”

“Please find the key to the house.”

Inside, there are comforting and intriguing nighttime things—a bed, many books—and outside, there are sources of light and joy—the moon, the sky—that reveal a reassuring order in the universe. This timeless bedtime story transports readers through the nighttime house, up into the sky, and back home while reminding us of the presence of love and wonder in our world.

Susan Marie Swanson’s spare verse and Beth Kromme’s breathtaking illustrations intertwine to create a comforting, magical story that will be revisited time and again.”

“Paul O. Zelinsky, unquestionably one of the most original and gifted children’s book illustrators, has once again brought forth a unique vision for an age-old tale with unrivaled emotional authority, control of space, and narrative capability. Few contemporary artists can match the level at which his paintings tell a story and exert their influence.
Beyond the Grimms, Zelinsky’s Rapunzel retelling can be traced back to a late-seventeenth-century French tale by Mlle. La Force based hers on the Neapolitan tale Petrosinella in a popular collection at the time. According to the artist, the fundamentals of the story are about possessiveness, confinement, and separation rather than punishment and deprivation. Thus, the tower given to Rapunzel by the sorceress is not a desolate, barren structure of denial but one of esoteric beauty on the outside and physical luxury on the inside. And the world the artist creates in his paintings through the palette, control of light, landscape, characters, architecture, interiors, and costumes speak to us not of an ugly witch cruelly imprisoning a beautiful young girl but of a mother figure who powerfully resists her child’s inevitable growth, and of a young woman and man who must struggle in the wilderness for the self-reliance that is the true beginning of their adulthood.

Paul O. Zelinsky’s work, as always, and yet always in a new and arresting way, thrillingly shows us the events of the story while guiding us beyond them to the truths that have made it endure.”

The Man Who Walked Between The Towers should be at the top of your list when considering the best books for kids. Based on the incredible true story of Philippe Petit’s death-defying tightrope walk between The World Trade Centre’s Twin Towers, this book is a truly gripping reading experience.

The lyrical words and lovely paintings capture every detail. At the same time, two dramatic foldout spreads create a sense of vertiginous drama as readers imagine themselves watching Petit walking, dancing, and performing high-wire tricks a quarter mile in the sky. It’s an amazing sensory journey that children of all ages will surely enjoy!

A wise story about a little princess who desired and received the moon. “Grown-ups will find the book to be hilariously funny… The lovely, squiggly color illustrations are just right.” -From The New Yorker.

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Ali Kaya


Ali Kaya

This is Ali. Bespectacled and mustachioed father, math blogger, and soccer player. I also do consult for global math and science startups.