In honor of 2021 Caldecott winner We Are Water Protectors, the first children's book by Indigenous creators to win the award, we rounded up more winning stories that will inspire kids from kindergarten to fifth grade.

By Margaret Kingsbury
January 29, 2021
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Caldecott-winning children's books have become synonymous with stories that last a life time. Named after 19th-century English illustrator Randolph J. Caldecott, the American Library Association awarded the first Caldecott Medal in 1938 to Animals of the Bible by Helen Dean Fish and illustrated by Dorothy P. Lathrop. Since then, it's awarded 84 medals to outstanding illustrated children's books, as well as honoring more than 100 other books.

This year, the 2021 Caldecott Medal was awarded for the first time to Indigenous creators Michaela Goade and Carole Lindstrom for their gorgeous picture book We Are Water Protectors. Inspired by Indigenous-led movements to protect our planet's water supply, this lyrical and accessible story can help begin conversations about environmentalism and water conservation. 

Credit: Art:Jillian Sellers.

With so many Caldecott winners, we thought we'd curate a list to make it a little easier for parents to find which Caldecott books are worth buying for their child's library. From hilarious books about fish and presidents to fascinating reads about planes and trains, these 20 stories are sure to delight young readers and their parents alike.

Caldecott Winners for Kindergarteners

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By Jon Klassen, 2013 Caldecott Medal

A little fish steals a hat from a much bigger fish and is confident the big fish will never notice. Except the big fish very much notices, and he wants his hat back. Children will have plenty of laughs at this hilarious book that overlaps the little fish's overconfidence with the bigger fish's determination. 

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Written by Ezra Jack Keats, 1963 Caldecott Medal

The Snowy Day was the first full-color picture book to feature a Black protagonist. This classic is a joyous story about a child discovering all the wonders in a snowy day. The vivid collage art pairs perfectly with the minimalist text.

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Written by Kevin Henkes, 2005 Caldecott Medal

This delightful and silly black and white picture book opens with Kitten mistaking the moon for a bowl of milk. What follows is a series of mishaps as Kitten attempts to lap up the moon. With bold, simple text, this engaging story is excellent for beginning readers.

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Written by Susan Marie Swanson, illustrated by Beth Krommes, 2009 Caldecott Medal

In exquisite black, white, and gold scratchboard illustrations, this bedtime story will delight young readers. Each illustration has fun things for children to notice, like a kitten tucked into a dresser drawer and a swing hanging from a tree. The poetic text is sure to help lull children to sleep.

Caldecott Winners for First Graders

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Written by Carole Lindstrom, illustrated by Michaela Goade, 2021 Caldecott Medal

In this stunningly illustrated picture book, a young Ojibwe girl recalls her grandmother's wisdom and stories about water and gives a rallying cry to protect Earth's water. 

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Written by Dan Santat, 2015 Caldecott Medal

This vibrantly illustrated and magical tale begins on an island where imaginary friends are born. But when Beekle is born, no child comes to claim him. He waits and waits but finely decides to venture out into the real world and find his child.

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Written by by Maurice Sendak, 1964 Caldecott Medal

This dark, fantastical classic remains as popular today as it was in the 60s. When Max gets into mischief, his mother sends him to bed without his supper. He escapes into his imagination, where he travels to the land of wild things, becomes their king, and joins their revels. 

Caldecott Winners for Second Graders

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Written by Kwame Alexander, illustrated by Kadir Nelson, 2020 Caldecott Medal

Kwame Alexander's stunning poem commemorates Black U.S. history and endurance, from the trauma of slavery to the Civil Rights Movement. The simple and beautiful prose allows for much discussion, as do the gorgeous realistic paintings by Kadir Nelson, who also won the Coretta Scott King Award for his illustrations. This contemporary classic makes for a fantastic starting point in talking about Black history.

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Written by Jane Yolen, illustrated by John Schoenherr, 1988 Caldecott Medal

A father and daughter share a special moment when they go on a nighttime adventure owling. The poetic prose and lovely watercolor paintings perfectly capture the relationship between both father and daughter and between humans and nature. Jane Yolen has written hundreds of children's books, though Owl Moon is the only one to win the Caldecott.

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Written by Alice and Martin Provensen, 1984 Caldecott Medal

The Glorious Flight tells the true story of Louis Bleriot, referred to as "Papa" in the text, and his determination to build a plane of his own. He persists through many failures, finally succeeding in making a plane in 1909. The stylized, sepia-toned illustrations perfectly evoke the early 1900s. This picture book biography is both a great read for aviation-minded children as well as an excellent book about learning from failure.

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Written by Allen Say, 1994 Caldecott Medal

In this picture book biography, author and illustrator Allen Say pays tribute to his grandfather in simple yet lyrical prose that explores his grandfather's homesickness as he moved between Japan and California. Say's realistic paintings are reminiscent of photographs and show the nostalgia his grandfather felt for both countries. It's a lovely picture book for exploring immigration.

Caldecott Winners for Third Graders

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Written by Javaka Steptoe, 2017 Caldecott Medal

Like with The Undefeated, author and illustrator Javaka Steptoe won both the Caldecott Medal and the Coretta Scott King Award for Radiant Child, a stunning picture book biography about artist Jean-Michel Basquiat. Jean-Michel Basquiat was an American artist in the 70s and 80s, whose collage-style art and merging of text and art transformed the art scene. In creating this picture book, Steptoe also used found materials and collage in homage to Basquiat's life and work.

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Written by Lindsay Mattick, illustrated by Sophie Blackall, 2016 Caldecott Medal

Finding Winnie tells the true story of the real bear from Winnie the Pooh. Captain Harry Colebourn rescued the bear cub and named him Winnie. He brought Winnie with him while on duty during WWI, and eventually, Winnie ended up in the London Zoo and met Christopher Robin. Author Lindsay Marrick is the granddaughter of Captain Harry Colebourn, and her historically accurate and engaging prose paired with Sophie Blackall's colorful and detailed illustrations create a moving story about both Winnie and WWI.

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Written by Chris Van Allsburg, 1982 Caldecott Medal

Two bored children discover an unforgettable board game in this classic picture book by multiple Caldecott Award winner Chris Van Allsburg (he won again in 1986 for The Polar Express). The intricately detailed and realistic black and white illustrations contrast to the surreal and sometimes frightening surprises the board game reveals. This adventurous read will captivate and thrill children.

Caldecott Winners for Fourth Graders

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Written by by Brian Floca, 2014 Caldecott Medal Winner

Children can learn about the transcontinental railroad in Brian Floca's historical picture book Locomotive. Full of sensory descriptions and historical details, the prose is as engaging and fast-paced as the train itself. With beautiful illustrations and front and back matter providing additional historical notes, this is a book readers can enjoy for a long time.

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Written by by Ed Young, 1990 Caldecott Medal

This Chinese version of "Little Red Riding Hood" depicts children saving themselves from the sinister Grandmother Wolf. The impressionistic watercolor illustrations contribute to the sense of danger and drama in the story. The cleverness of the children makes for a refreshing change from European versions of the tale. Children who enjoy fairytales or darker themes will find a lot to love with this one.

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Written Judith St. George, illustrated by David Small, 2001 Caldecott Medal

This funny and engaging nonfiction children's book presents quirky facts about the presidents alongside equally quirky illustrations. Children can have a good laugh while also learning about U.S. history. Parents may even learn a thing or two from it too.

Caldecott Winners for Fifth Graders

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Written by Margaret Musgrove, illustrated by Leo and Diane Dillon, 1977 Caldecott Medal

This gorgeously illustrated alphabet book of African traditions was the second consecutive Caldecott win for Leo and Diane Dillon, who first took home the medal for Why Mosquitoes Buzz in People's Ears. The text proceeds through each letter describing an aspect of African tradition. It's a fascinating read paired with stunning and intricate illustrations.

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Written by David Wisniewski, 1997 Caldecott Medal

A golem is a person made from clay and derives from Jewish folklore. David Wisniewski retells the golem's origin story in this intense and striking picture book paired with his compelling papercut illustrations. The story addresses anti-Semitism, and Wisniewski gives further background about the golem in Jewish folklore in the back.

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Written by Brian Selznick, 2008 Caldecott Medal

It's rare for a chapter book to win a Caldecott Medal, but Selznick's stunning illustrations earned him the award. The novel takes place in a 1930s train station in Paris, where orphan Hugo helps his uncle keep the clocks and tinkers with an automaton. A mystery unfolds after an encounter with a toymaker. Told both in illustrated panels and text, this beautiful novel will enchant readers of all ages.

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