The role of philanthropy in K-12 public education has historically ebbed and flowed in relation to public expenditures. Early K-12 education philanthropy peaked during and after the Civil War when philanthropists supported education for emancipated slaves through initiatives like Freeman’s Bureau, Slater Fund and Rosenwald Schools until state and federal governments assumed responsibility (Bremner, 1988; Finkenbine, 2003; Fleishman, 2009; Mays, 2006; Stephenson, 2012). With sufficient public support, K-12 education philanthropy did not see its next major wave of investments until the 1990s, with significant increases occurring after 2000. From 2000-2010 the number of education related grants from major national philanthropists increased from 1,200 to 2,600, and the amount of total funding, $486 million to $843 million (Reckhow & Snyder, 2014, p.3). The latest wave of education philanthropy occurs at the intersection of two key events: Funding challenges for public education and increasing philanthropic resources particularly among a new generation of philanthropists. While significant philanthropic resources have poured into K-12 public education, they are more likely to support changes in education policy than to provide direct support to the schools (Ferris, Hentschke, & Harmssen, 2008; Greene, 2015). In addition, rural communities receive very little support from national education philanthropy. Vermont is a rural state with a relatively successful K-12 public school system that faces significant funding challenges (Pache, 2017; Valley News, 2015). The questions at the core of this research are what role does philanthropy play in Vermont K-12 public education and what role might it play? To answer these questions, the literature provides a foundation by exploring the history of philanthropy in general, and specifically education philanthropy. Further literature review examines the current trends of using philanthropy to shape national education policy and fund programs that compete with public education. A gap in the research on rural philanthropy and rural K-12 education philanthropy provides the impetus for the focus on the rural schools in Vermont. The study focuses on two geographically defined regions in Vermont that utilize two different models of place-based philanthropy to support their public schools. The two case studies include interviews with 24 participants with backgrounds in and knowledge about education and philanthropy. In addition, document review was used to support and triangulate the findings. The findings, presented for each case and in a cross-case analysis, reveal the effective and unique ways these two rural areas use philanthropy to support its K-12 public schools. One model was regional with a focus on broad program support through use of local nonprofits, while the second model was town specific and provided direct support to the local schools. Both cases demonstrate the challenges and opportunities associated with place-based philanthropy. The conclusion offers further information on how schools and communities might develop their own place-based philanthropy.