Outdoor leaders have an opportunity to promote and facilitate a bond with the out- of-doors, yet little research has been conducted to describe the evolving relationships between outdoor leaders and the natural environments with which they come into contact. The purpose of this study was to describe the perceptions of outdoor leaders toward the ways they feel connected to nature places. The outdoor leaders (N = 20) were undergraduate students, graduate students, faculty and staff at a large university in the midwestern United States. These participants completed a Q sorting procedure that reflected their attitudes of connectedness to places in outdoor settings. Q sorting falls within the conceptual framework of Q methodology, a research strategy that explores and measures subjectivity. The results of the sorting procedure were analysed by correlating the sorts, factor analysis of the correlation, followed by rotation and z-score calculation of each statement for each factor. The results are described as a two factor solution reflecting two different views of outdoor leaders toward the ways they feel connected to places in nature and were named as; (1) Deep-spirit and (2) Nature-emotion.