Freckleface Strawberry is a direct musical adaptation of the children's book of the same name written by actress, Julianne Moore. Moore based the book on experiences that she had as a child with red hair and freckles. She wanted to write a book that emphasized a message of self-acceptance and self-confidence. Rose Caiola picked up a copy of the book and was inspired to turn it into a musical. The initial workshop of the musical involved 23 child actors, although the producers eventually decided to use adult actors in only seven roles.
Freckleface Strawberry, with music and lyrics by Gary Kupper and book by Gary Kupper and Rose Caiola, opened at New York's New World Stages on October 1, 2010. It closed six months later and eventually moved to the MMAC Theater at the Manhattan Movement and Arts Center, where it played until July 1, 2012. After closing, a national tour launched. The tour is notable for casting child actors in the child roles, whereas the roles were previously being performed by adults.