Unmanaged recreation presents a challenge to both researchers and managers of outdoor recreation in the United States because it is shrouded in uncertainty resulting from disagreement over the definition of the problem, the strategies for resolving the problem, and the outcomes of management. Incomplete knowledge about recreation visitors’ values and relationships with one another, other stakeholders, and the land further complicate the problem. Uncertainty and social complexity make the unmanaged recreation issue a wicked problem. We describe the wickedness inherent in unmanaged recreation and some of the implications of wickedness for addressing the problem for the Front Range of the Rocky Mountains in Colorado. Conclusions about the nature of the problem are based on a problem appraisal that included a literature review and interviews of key informants. Addressing wickedness calls for institutional changes that allow for and reward the use of trust building, inclusive communication, and genuinely collaborative processes.