This chapter examines the work of Pura Belpré, an educated mulatto woman of modest means who, like so many islanders, came from Puerto Rico to the U.S. mainland in the 1920s. This chapter primarily examines “Bilingual Storyteller” and her piece “I Wished to Be Like Johnny Appleseed” referencing the interwar period. The rich material in these texts allows for a reconstruction of the social tensions regarding how ‘womanhood’ and ‘race’ were interwoven within her writings during those pivotal decades, thereby providing a more accurate yet conflicting register of how [gendered and racialized] colonial selves, such as Belpré, were being read—textually and bodily. Such was the case regarding how she functioned within—and was seen by—the city’s ethno-racially polarized Hispanic and North Americans. Moreover, this chapter shows how her work centered on the importance of cultural identity in the lives of Puerto Rican migrant children. The chapter distinguishes her trajectory as an interlocutor of the Harlem Renaissance and the Schomburg Center of Black Culture, which set her apart from other educated Puerto Rican women who had migrated to New York City at this time.