Background: Parks and recreational facilities in the Canadian context are critically important to overall wellbeing as they provide opportunities to connect with nature, mitigate climate change, and facilitate social connections for the entire population. The ParkSeek project is a national research initiative funded by the Public Health Agency of Canada to establish a self-sustaining suite of tools to support the surveillance of parks and recreational facilities as health promoting resources. Methods: A geographic ecological momentary assessment tool (GEMA) was developed to survey participants via their smartphone device in real-time about their experiences in parks, relating it to their WHO-5 wellbeing score, and sleep quality score. Participants complete these surveys twice per day, and whenever entering or exiting a park. Participants were recruited from the mid-sized Canadian cities of London, Ontario and Waterloo, Ontario. In addition, the research team evaluated the physical features of parks visited by participants using a standardized audit tool and incorporated these features into analyses of park experiences and wellbeing outcomes. Results: Pilot results demonstrate participants engage with parks based on their perceived features rather than objective features as measured by the research team, with moderate changes to their self-reported wellbeing and sleep quality scores. The time spent in parks, and daily exposure to greenness outside of parks may mediate these relationships. Conclusions: The advent of “park prescriptions” in Canadian primary care and public health practice requires further monitoring and evaluation. The ParkSeek GEMA could be used to monitor the effectiveness of these prescriptions in responding to mental wellbeing and physical health conditions.