The purpose of this study was to examine teacher retention and attrition in rural New Hampshire schools and to that end better understand why teachers choose to stay employed in rural New Hampshire schools. The literature suggests that rural schools are most at risk for retaining highly qualified teachers (Guha, Heally & Adams, 2016; Hyler & Darling-Hamond, 2017; Kaden, Patterson, Malloy, & Allen, 2007). This study focused on New Hampshire rural schools because of the uniqueness of the state’s rural contexts. Based on the review of literature, teacher working conditions, overall job satisfaction, and community engagement informed the conceptual framework that guided this study (Ashiedu & Scott-Ladd, 2012; Darling-Hammond, 2003; Glover et. al., 2016; Hanushek, & Rivkin, 2007; Howley & Howley, 2005; Johnson, Kraft & Papay, 2012; Ladd, 2011; Monk, 2007; Schafft, 2006). This qualitative multi case study was conducted to better understand why teachers choose to stay employed in rural New Hampshire schools, and how the state’s different rural contexts influence teacher retention. The study included three schools, located in the three most rural regions of New Hampshire. Each was considered through sampling procedures to best represent their specific rural context. A cross case analysis was conducted to account for generalizations across all contexts. Data was collected for this qualitative study using pertinent document reviews, administrative interviews, and teacher focus groups. Results from this study revealed insights into why teachers choose to stay employed in rural New Hampshire Schools. This study illuminated the unique sense of place of each school and how each rural context is affected by and addresses teacher retention. The findings of this study suggest teachers will forgo working conditions for strong levels of job satisfaction and community engagement, retaining supportive school leaders supports overall teacher job satisfaction necessary for teacher retention, engagement does not occur in isolation, and personal considerations both draw and remove teachers to and from rural communities. The conclusions of this study identify areas in which rural schools can effectively maintain a highly competent and consistent teaching staff. This could prove advantageous for the continued sustainability of rural schools, rural communities, as well as the state of New Hampshire in general.