Hyperlocal websites provide a platform for individuals to share plant and animal sightings with others in the same natural setting. Studying what members of the public spontaneously find noteworthy and how they choose to convey observations from a particular location can provide useful guidance for citizen science research into participants’ motivations and technology use. Over the past three years, approximately 100 unique observers have posted about 300 sightings along a 9-mile creek in the greater Washington, DC, area. This presentation uses results from descriptive analysis, visualization, and content analysis to explore the most common classes represented among the sightings (birds, followed by mammals), the species that constitute charismatic megaflora in a mid-Atlantic greenway, the most common categories for observations (describing behaviors, making identifications, and observing quantities), and the social context in which the sightings are undertaken and their role in building community cohesion. Inductive thematic analysis of interviews with 9 habitat and park experts and technology designers provides additional insight into the observation activity, the motivations and behaviors of those who practice it--including hyperlocality, sustainability, and teaching and learning about nature--and the role that technology plays in supporting observations among non-experts. Functions of the tools and technologies reported include 1) supporting overall communications about, and involvement in, outdoor experiences; 2) capturing, viewing, and displaying specific images; 3) looking up information to validate identifications; 4) conducting citizen science activities; and 5) navigating terrain while on site. Contributions of the work include the application of a temporal model from parks and recreation research (Clawson and Knetsch, 1966; McKay, Brownlee, and Hallo, 2012) to determine when various tools and technologies can be deployed most effectively and the creation of a set of research-based design guidelines that identify logistical, content-oriented, and social features of future technologies to support hyperlocal nature observations.