Previous research has indicated that urban agriculture offers a wide variety of health, economic, and social benefits for participants. Urban farms need to consider what factors and mechanisms allow them to engage more of their community to share these benefits. Examining four case studies of urban farms across Philadelphia, this paper strives to illuminate the lessons and themes of community engagement in urban agriculture. I draw upon information from prior research, online sources, in-person site visits, and semi-structured interviews with farm operators. The findings offer insight into how events and programming, marketing and outreach, leadership and vision, funding and partnerships, and physical design all interact to shape an urban farm’s ability to engage with its community.