Aldo Leopold is widely regarded as one of the founders of the modern field of ecology. He was also a skilled woodsman, hunter, and a proponent of personal development through time in the outdoors. In this essay, we focus on how Leopold viewed certain benefits concomitant with immersive outdoor experiences. Guided by his 1943 essay, "The Flambeau," we highlight the importance Leopold placed on opportunities for trial-and-error through primary experience in nature for youth, while asking if these freedoms still exist in the Anthropocene. We then present four broad and interrelated social-ecological dimensions -- record visitation, climate impacts across boundaries, last-chance tourism and volatility in governance -- facing park and protected area managers, and outdoor and environmental educators who are the caretakers of these freedoms. Despite these challenges, we close by asserting the importance of a youth agenda to maintain access to experiences that provide young adults opportunities for risk and exploration. These experiences are paramount for both their intrinsic value and their potential to inculcate environmental ethics in future generations.