Back To School & Office30 Beloved Caldecott Winners Students Should Know

30 Beloved Caldecott Winners Students Should Know


In 1938, the first Caldecott medal winner was awarded to the most distinguished American picture book. Since then, several hundred books have become Caldecott winners or honor books. Many of these are now classic favorites, read by generation after generation. Here are 30 of the best, including familiar titles and new ones just waiting to be discovered.

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Combining black-and-white photos with bright illustrations, this Mo Willems book is ultra-relatable for any kid with a favorite stuffed animal. They’ll breathe a sigh of relief at the happy ending. (Pre-K)

2. Olivia by Ian Falconer

Olivia (Caldecott Winners)

Olivia is good at lots of things. In her bright red dress and distinctive black-and-white striped stockings, she shows off her many talents for readers to enjoy. (Pre-K)

Blueberries for Sal by Robert McCloskey

Sal is picking blueberries when she runs into a mama bear preparing for winter with her cub. Her sweet tale has been beloved since it was published in 1948. (Pre-K–Kindergarten)

Where the Wild Things Are

Perhaps the most beloved Caldecott medalist of all time, Sendak’s classic belongs on every kids’ bookshelf. When Max (dressed in his wolf suit) causes trouble, his mother sends him to bed. Little does she know—he’s off to the land where the wild things are! (Pre-K–Kindergarten)

No, David! (Caldecott Winners)

Mischievous toddlers will see themselves in loveable, troublemaker David! The pictures in this one are so much fun, it’s easy to see why it’s a Caldecott favorite. (Pre-K–Kindergarten)

Don't Let the Pigeon Drive the Bus!

Mo Willems has been a classroom favorite for almost two decades now. This is his first picture book, and it’s a hilarious back-and-forth between a wheedling pigeon and the readers. If ever a book was made for a read-along, this is it! (Pre-K–Kindergarten)

The Snowy Day (Caldecott Winners)

This classic perfectly captures the feeling of the first snow of winter! The Snowy Day was the first Caldecott winner to feature a main character of color, giving it a special place in many readers’ hearts. (Pre-K–Kindergarten)

Strega Nona (Caldecott Winners)

Strega Nona’s magical pasta pot is a boon to the whole town. But one day, when she’s gone, Big Anthony recites the magic words over the pot, and chaos ensues! (Pre-K—Gr. 1)

Click, Clack, Moo Cows That Type

You might have to show kids what a typewriter actually is first. But they’ll love the hilarious antics of Farmer Brown’s typewriting cows! This one has become a modern classic, spawning a whole Click, Clack series. (Pre-K—Gr. 1)

10. Last Stop on Market Street written by Matt de la Peña and illustrated by Christian Robinson

Last Stop on Market Street

As CJ and his nana ride the bus, he wonders why they don’t have a car or live in a nicer part of town. His nana’s encouraging answers help him see the beauty and joy in his own daily life. (Pre-K–Gr. 1)

11. Madeline by Ludwig Bemelmans

Madeline (Caldecott Winners)

Madeline is one of “twelve little girls/in two straight lines” who live in Paris. Brave Madeline isn’t afraid of anything, and generations of children have grown to love her. (Pre-K–Gr. 1)

Make Way for Ducklings

This is one of the oldest Caldecott winners on our list, but it remains as fresh and sweet as it did in 1941. Follow a flock of ducklings and their mama as they make their way to a new home in the Boston Public Gardens. (Pre-K–Gr. 1)

This Is Not My Hat

A sneaky little fish has stolen a bowler hat. Will he get away with his crime, or will his fellow sea creatures give him away? An ambiguous ending leaves it up to the reader to decide! (Pre-K–Gr. 1)

14. Tuesday by David Wiesner

Tuesday (Caldecott Winners)

Find the magic in an average day with this nearly-wordless story, told through imaginative pictures of floating frogs and other improbable events. There’s something new to discover in the illustrations every time you read it. (Pre-K–Gr. 1)

15. We Are Water Protectors written by Carole Lindstrom and illustrated by Michaela Goade

We Are Water Protectors

One of the newest Caldecott winners, this 2021 selection is a rallying cry from indigenous people to help protect our most valuable resource—water. Lush illustrations complement the lyrical prose, calling us all to be water protectors. (Pre-K—Gr. 2)

Anansi the Spider by Gerald McDermott (Caldecott Winners)

Anansi is one of the most important characters in West African, African-American, and Caribbean folklore. Bright colors and geometric patterns make this version of his tale a memorable classic. (Pre-K–Gr. 2)

17. The Cat Man of Aleppo written by Irene Latham/Karim Shamsi-Basha and illustrated by Yuko Shimizu

The Cat Man of Aleppo

The true story of Mohammad Alaa Aljaleel will resonate with animal-loving kids. Alaa braved the horrors of the Syrian civil war to offer safe haven to the city’s abandoned animals. The realistic illustrations plunge readers into the heart of the action. (Pre-K–Gr. 2)

Sylvester and the Magic Pebble

Sylvester the donkey loves to collect unusual pebbles. One day, he finds a pebble that grants him his wish to turn into a rock to avoid a nearby lion. Unfortunately, the pebble rolls off the rock, and Sylvester is unable to reverse the wish. Watercolor originals illustrate this charming tale, which has a happy ending at last! (Pre-K–Gr. 2)

19. Owl Moon written by Jane Yolen and illustrated by John Schoenherr

Owl Moon

When you go owling, you have to be quiet. Take a journey through the snowy woods on the hunt for the majestic nighttime fliers with a little girl and her father. (Pre-K–Gr. 2)

The Polar Express (Caldecott Winners)

Before it was a popular holiday movie, it was an award-winning book. Travel on the Polar Express in the original holiday tale, with rich illustrations that take you along for the ride. (Pre-K–Gr. 2)

Thank You, Omu! (Caldecott Winners)

Omu’s stew is so delicious that soon the community has eaten the whole pot, leaving nothing left for her. Fortunately, her neighbors have generous hearts of their own. (Pre-K–Gr. 3)

22. A Different Pond written by Bao Phi and illustrated by Thi Bui

A Different Pond (Caldecott Winners)

A boy and his father wake early to fish for much-needed food in a Minneapolis pond. While they do, the father tells his son of another pond on the other side of the world, in Vietnam. This book won multiple awards, and it’s definitely one of the newer Caldecott winners students should know. (Pre-K–Gr. 3)

23. Coming On Home Soon written by Jacqueline Woodson and illustrated by E. B. Lewis

Coming on Home Soon

It’s World War II, and Ada Ruth’s mama has to go to Chicago to work. Ada Ruth and her grandma stay behind, living their lives but waiting for the letter saying Mama will be coming on home soon. (Kindergarten–Gr. 3)

Frog and Toad are Friends (Caldecott Winners)

Frog and Toad turned 50 in 2020, and they’re just as popular as ever. Their gentle stories of friendship are written at the perfect level for beginning readers. The illustrations truly bring the characters to life. (Kindergarten–Gr. 3)

The Glorious Flight (Caldecott Winners)

The true story of a man determined to fly across the English Channel will capture kids’ imaginations and send them soaring. Despite the adventurous tale, the book itself is illustrated in quiet, muted colors that evoke a dreamy mood. (Kindergarten–Gr. 3)

Radiant Child: The Story of Young Artist Jean-Michel Basquiat

Kids who hate coloring inside the lines will love the story of Basquiat. His collage-style artwork exploded onto the scene in the 1980s, inspired by the energy of the world around him. The bold illustrations of this book match the engaging text. (Kindergarten–Gr. 4)

27. Jumanji by Chris Van Allsburg

Jumanji book cover

Published in 1981, this fantasy story became a certified classic when it hit the big screen in 1996. True fans know the book is just as engaging as it tells the exciting story of a board game come to life. (Gr. 1–4)

Grand Canyon by Jason Chin

Here’s another picture book that young kids will enjoy, but older kids will really get into. The details about the Grand Canyon’s natural history are beautifully illustrated. (Gr. 2–6)

The Invention of Hugo Cabret (Caldecott Winners

Hugo lives in the walls of a busy Paris train station, staying hidden until a mystery involving a message from his dead father draws him out. This chapter book depends as much on its 284 illustrations as it does on the words to tell its intriguing story. (Gr. 2–6)

30. Castle by David Macaulay

Castle by David Macaulay (Caldecott Winners)

Most Caldecott winners are for the younger crowd, but Macauley’s intricately-drawn works are ideal for older kids. Explore the planning and construction of a medieval castle and town in step-by-step detail. (Gr. 5-7)

What incredible Caldecott winners did we leave off our list? Come share your own favorites on the WeAreTeachers HELPLINE group on Facebook!

Plus, 28 classic picture books that will make you nostalgic for preschool .





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