There is an immense gap between the success that Maine's elementary school children achieve on national tests and the rate at which they go on to postsecondary education. This gap is not explained by Maine's low per capita income. Maine's homogeneous population created a culture valuing hard work, independence, pragmatism, family, community, tolerance of eccentricity, and love of the land, yet displaying characteristics of "peasant" society such as fatalism, pettiness, and insularity. Children are taught to respect adults, work hard, and graduate from high school, but the culture does not value postsecondary education. The state's history also impacts its educational system. Into the economic void resulting from the Civil War came paying guests searching for a romantic vision of Maine. Some visitors had different values and made local people serving them feel inferior, a pattern that continues. This dissertation examines the influence of culture and individual and collective histories on academic aspirations through an ethnographic case study of the small town of Tremont on Mount Desert Island, a resort area of rural Maine. Chapters discuss (1) research methods; (2) the development of self and aspirations; (3) the culture and history of Tremont, Maine, and the conflict between native and dominant cultures; (4) the history of Maine; (5) a portrait of Tremont; (6) schooling on Mount Desert Island; (7) the Tremont community and elementary school; (8) students' transition to the consolidated high school; (9) interviews about factors that influence student decisions about postsecondary education; and (10) conclusions and parallels to other rural experiences. An epilogue offers suggestions that build on the strengths of Tremont's people. Appendices describe the Student Aspirations Survey and present survey results. Contains tables, figures, charts, photographs, and 189 references. (Author/TD)