Set in turn-of-the-century New England, this musical tells the story of orphan Jerusha Abbott of the John Grier Residence and her mysterious benefactor who agrees to ship her to school, who she dubs "Daddy Lengthy Legs" after seeing his elongated shadow. Beneath the situations of her benefactor, Jerusha sends him a letter as soon as a month, describing her new-found experiences with life exterior the orphanage.