Understanding how individuals document and interpret their encounters with the natural world can aid citizen science researchers and project managers as they consider issues of volunteer engagement and use of information and communications technology in urban settings.This Capstone project provides an analysis of 275+ plant and animal observations contributed to a community website (Friends of Sligo Creek) by nearly 100 volunteers over a 3-year period from 2011 to 2013 to address questions such as, Who were the most frequent contributors? When did they conduct their observations? What categories of flora and fauna did they observe most frequently? How did they document their sightings? What appeared to be the rationale for their selections? How do these data change over the three-year period under study? Based on content analysis, contributors used their observations to describe behaviors, acknowledge the web of life, describe sounds, make identifications, observe frequencies, observe quantities, observe something rare or unusual, anthropomorphize, express appreciation/wonder/awe, and reinforce social ties. In addition, transcripts from 9 expert interviews were analyzed, yielding insight into subthemes of hyperlocality, sustainability practices, teaching and learning about nature—who and how, technology used or proposed at various times and contexts, and values associated with the technology—positive, neutral, negative. Technology recommendations were then provided to address logistical, content, and social issues that grew out of the research.