What do students learn when they engage in public-facing interdisciplinary digital research with tangible community-oriented outcomes? Using a case study of the Ready Set Fit smartphone app, we explore the deep learning that occurs when students engage in an ambitious software development and content-design project conducted outside usual course structures. Ready Set Fit, a student developed smartphone app, brings together wellness, place-based learning, and crowdsourced walking paths. Responding to an expressed need to motivate exercise among the “pre-sick,” the app guides and informs the user along a selected themed walking path, each of which contains a collection of significant locations. An integral part of this project has been to engage community partners to create paths that have cultural and historical significance for that area. Such collaboration with community partners demands new skills of students and faculty mentors alike as each partner has a unique set of values, objectives, and resources.