Wilderness trips have become increasingly popular, especially in the adolescent population. The wilderness can be a source of rejuvenation while being mentally and physically challenging; however, it is also fraught with the potential for injury, illness, and even death. Epidemiologic studies of injuries and illnesses from hikers are not extensive, but there are sufficient data to identify the most common risk factors to offer some strategies for prevention. Many youth will have a medical visit or preparticipation physical assessment before an organized wilderness experience. This article highlights commonly seen wilderness injuries and illnesses and provides guidance for proper planning and problem solving.