Trending to the future, there currently exists a large dialogue in regards to reduced development of nature-connections within future generations. These connections, often defined as an individual’s personal oneness with what they consider nature, have been measured in past studies of which high degrees of connectedness were linked to environmental behavior. Thus, with research suggesting declines in connectedness, health of natural environments could be threatened. This research aimed to analyze this issue through the lens of urban youth in attendance of an environmentally focused high school. In providing students artistic venues through which to express their beliefs and own personal experiences in developing nature-connections, new insight into this complicated topic was unearthed. Among key points include an understanding that nature-connections are highly fluid, perception of nature as being largely based on familiarity, and the emergence of new venues through which to engage with nature—namely internet blogging. Furthermore, the environmental education as conducted at this high school was deemed effective due to its truly immersive philosophy and largely due to its non-urban, forested location.