Caroline Pratt, the founder of the City and Country School, is one of the few educators who tried to work out a program that would engage and develop students’ imaginations. Along with other progressive educators, however, she has been criticized for her child-centeredness, that is, valuing children’s spontaneity at the expense of planning and structure. In this paper, I will argue that this criticism does not apply to Pratt and describe her ideas of curriculum. The examination is largely historical, but it also has a conceptual component in that I try to show how the ideas of imagination and curriculum are compatible. © 2018, Springer Science+Business Media B.V., part of Springer Nature.