Caldecott Medal 1960s: A decade of winners

The 1960s were a transformative decade for children’s literature, and nowhere is that evolution more apparent than in the winners of the Caldecott Medal, the prestigious award honoring the year’s most distinguished American picture book. This was the era when picture books shed their purely instructional purpose and became genuine works of art—where illustration techniques grew more daring, storytelling more imaginative, and the relationship between words and images more sophisticated. The award itself seemed to recognize this shift, celebrating creators who weren’t content to simply decorate a page but instead understood that a picture book was its own complete artistic medium.

Consider the arc of innovation across just a handful of standout winners: Marie Hall Ets’s Nine Days to Christmas opened the decade with its charming exploration of Mexican holiday traditions, while Maurice Sendak’s Where the Wild Things Are in 1964 fundamentally changed what picture books could be—a psychological journey wrapped in wild adventure that spoke to children’s inner lives in ways the format had rarely attempted before. By mid-decade, illustrators like Marcia Brown and Ezra Jack Keats were pushing artistic boundaries with every award they won; Keats’s The Snowy Day became an instant classic with its innovative collage technique and groundbreaking representation of a Black protagonist in mainstream children’s literature. The decade concluded with Uri Shulevitz’s The Fool of the World and the Flying Ship, a Caldecott Medal winner that drew from Russian folklore and proved the award’s appetite for international stories and fantastical visual storytelling.

These ten years established the Caldecott Medal’s role as a tastemaker that could elevate not just individual books but entire approaches to the art form. Below, explore the complete list of 1960s winners and rediscover the picture books that shaped a generation.