This essay describes a literacy project involving college students who are preservice teachers and students in an urban alternative public school. Robert Frost’s “The Road Not Taken” served as a touchstone or linchpin for the development of literacy skills and identity construction for both the college and secondary school students. Utilizing the idea of “a new neighborhood” as a metaphor and a goal, all students were given opportunities to engage with language, opening them up to a variety of new experiences and a new sense of belonging within a safe classroom environment.