Many high-profile urban parks in the US are experiencing a resurgence not seen since the late nineteenth century due to an influx of funding from private philanthropic organisations. Conversely, despite being essential spaces for rural quality of life, rural parks have struggled to attract private funding. This article compares two urban and two rural case studies to reveal this funding discrepancy. The comparison is used to identify the many roles urban parks play, which make them ideal opportunities for philanthropic funding, and, subsequently, the limitations that rural parks face when attracting similar investment. Ultimately, this article finds that rural parks struggle to attract private investors because rural areas’ inherently boundless and jurisdictionally ambiguous reality fails to provide most corporate philanthropic organisations and municipal leaders with a clear and mutually beneficial suite of financial and political benefits.