Keeping forestland intact has emerged as a critical policy objective at state and federal levels. This target has been supported by substantial public investment. The collective impact from the bequest decisions of millions of landowning individuals and families has the potential to affect the extent and functionality of future forests in the United States. Despite a growing body of research devoted to studying these transitions in forest ownership, much remains unknown about how family forest owners make decisions in this arena. The social and emotional dimensions of woodland succession planning have been particularly under-examined. This thesis explores the process of planning for the future use and ownership of woodlands through in-depth analysis of 32 semi-structured interviews with family forest owners in Massachusetts, Maine, New York, and Vermont. The first article investigates how family forest owners evaluate and integrate stories derived from their social networks when planning for the future of their woodlands. Analysis of the themes contained in stories framed as “cautionary tales” revealed common fears surrounding succession planning. The second article explores the complexity of emotional relationships with family forests showing how emotional geographies manifest in the succession planning process. Together, these studies deepen understanding of how family forest owners plan for the future of private woodlands and offer implications for Extension and outreach.