One of the interesting behaviors practiced by citizens across the globe is the pursuit of outdoor recreational activities featuring elements of personal risk and danger. These types of activities are now becoming a global mainstay for many individuals, economies, and organizations. This study examined the underlying motivations and subsequent behaviors associated with risk-taking recreational activities and used the concepts of eudaimonics and hedonics to examine the motivations for participation from individuals engaging in three different adventure activities occurring in eight different locations. Recruitment took place in several forms, including in-person solicitation of participants at the activity areas, which consisted of mountain biking trailheads, rock climbing areas, and whitewater sites. Data were collected from three popular outdoor adventure activities (OAAs), including mountain biking, rock climbing, and whitewater boating. This study employed the use of multivariate analysis of variance (MANOVA) to investigate the relationship between two independent variable sets, including (1) the activity type, and (2) the level of experience, gender, type of activity, and the dependent variables of the Hedonic and Eudaimonic Motives for Activities (HEMA) scale (eudaimonic and hedonic). In addition, a cumulative odds ordinal logistic regression with proportional odds was utilized to determine the effects of expertise level and activity type on reported eudaimonic and hedonic motivations. A qualitative interview process was utilized to further investigate participant responses surrounding eudaimonic and hedonic motivational perspectives. The results indicated slight variations in experience level in the underlying motivations. Furthermore, qualitative inquiry revealed several motivation categories and diversity in the way those motivations were present throughout the recreation activity.