Many cities are making substantial capital investments in urban tree planting. Residents play active and diverse roles in enhancing and protecting the urban forest, and are therefore critical to many municipal-level policy objectives. The way residents perceive and value the urban forest can have implications for achieving urban forestry goals through residents and volunteers. However, urban residents are not a monolithic block or homogenous category; instead, they have diverse opinions, needs, and constraints. Moreover, relatively little is known about how residents hear about available resources, such as free trees, and decide to 'opt-in' to tree planting initiatives, choosing to plant and maintain trees on or near their properties. The focus of this study was to address three questions about participation in a request-driven program that provides free street trees to residents of New Haven, Connecticut, U.S.: 1) Who requests trees through this program? 2) How did the requesters hear about this program? 3) Why did residents request free street trees? Survey respondents were primarily long-term residents of New Haven; mostly learned about the opportunity from their neighbors; and requested a street tree to replace a removed tree, because they value the aesthetics, and to a lesser extent the environmental benefits. Future research should systematically investigate differences between participants and non-participants in local tree planting initiatives, exploring possible trends across cities and programs. Such studies would identify opportunities and barriers to engaging private residents in efforts aimed at increasing canopy.