In times of crisis, what tools do planners and designers have to inspire a sense of well-being? How can we heal community through dialogue, recognizing the ongoing need for connection with or without a crisis? Are there ways to uncover unknown concerns and values in a community? The engagement approaches many planners and designers rely on do not typically aim to access these deeper questions in society. Surveys, public meetings and focus groups seek tangible results that target specific issues. They are often conducted out of context, taking the public out of the environment at issue to answer questions on a defined topic. What tools do professionals designing our urban environments have for discovering unknown issues in a more spontaneous and practice-based way in places where community exists? Through the Eudaimonic Tree Pilot I explored these questions, using the framework of eudaimonia to guide my process. The objective of my study began with my desire to inspire a sense of well-being, eudaimonia, in my community during a time of great loneliness and mental health decline due to the ongoing COVID-19 pandemic. This historic moment left many people feeling disconnected and hopeless, exacerbating a national trend that started well before COVID (Ammar et al., 2021). In response, I produced three installations using trees in the landscape to offer the public a means of expression. Each tree housed a different prompt rooted in eudaimonic sentiments and blank note cards for public response. Their messages hung from tree limbs and became an embodiment of the collective consciousness. This study of public engagement through participatory art unearthed profound implications for the planning and design fields. Some of the primary takeaways suggest that participatory art can catalyze community dialogue; spontaneity heightens co-creation; and highly co-created initiatives are likely to generate a eudaimonic effect. This process was led by results as they emerged, highlighting previously unknown resolutions and considerations. This heuristic, emergent methodology could be used more often by planning and design professionals as a means to perform design research that embraces the ephemeral and eudaimonic aspects of communities.