The K–12 American education system is inundated with school reform policies and legislation that aim to transform schools from low-performing to high-performing academic institutions. Through the conceptual framework of school improvement, this case study examined the educational reform journeys of two rural Maine high schools that were officially identified by the State as failing schools in 2010 because they did not achieve Adequate Yearly Progress. A major difference between the two schools was one school applied for and accepted a federal School Improvement Grant (SIG) and the other school did not. By 2013, both of these schools attained turnaround status and are no longer designated as “persistently low-achieving.” This case study sought to understand the role of leadership, instruction, school culture, and financial resources in improving persistently low academic achievement at the high school level in rural areas. Maine state assessment data in the content areas of reading and mathematics were analyzed for statistical significance over a six-year span that included pre- and post-turnaround years. Qualitative data were used to describe the action steps of each school and the reasons for the reform paths they chose. This mixed methods research provided a fuller description of the journeys of these two schools. The findings, reflections, conclusions and recommendations offer insight and new learning for school reform efforts in rural locations.