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"We are all segregated in the prison of class," mused turn-of-the-century literature professor Vida Dutton Scudder. "More than we recognize, our inner life is shaped by the traditions of the group to which we happen to belong; and until we escape from such prison, at least through imagination, or better far through personal contacts, our culture is bound to remain tragically cramped and incomplete" (On Journey 67-68). In innovative literature courses, Scudder offered college students escapes from their class prisons through "imagination." She facilitated "personal contacts" by encouraging students to work with people of other classes and races in inner-city settlement houses she had founded. In this essay, I argue that Scudder's pedagogy predicted a college-community connection increasingly popular one hundred years later: service-learning. I outline Scudder's teaching, settlement work, and the ideologies underlying both; critique her work with the benefit of twenty-first-century hindsight; and conclude by reaffirming that in the context of her times she was a remarkable figure. Although I focus primarily on the young women Scudder taught and supervised in the settlements, I consider as well settlements' complicated relationships with the inner-city communities in which they were located.