Born October 25, 1875, in Hoosick Falls, New York, Carolyn Sherwin Bailey was interested in writing from a very early age. Even before she knew how to write, she dictated stories to her mother, who was a mathematics teacher and a writer. Until she was twelve, she was educated at home. During this time, her grandmother gave her the real Miss Hickory, a doll made from a pattern from pioneer days. By the time she was nineteen, Bailey's work was being published, and she wrote books for children for the rest of her life.

Bailey attended Teachers College at Columbia University. She later taught school and rose to become a principal in addition to editing a children's magazine and continuing her writing career. In 1947 she won the Newbery Prize for Miss Hickory.