This paper presents the experiences and lessons learned from small food store interventions in four U.S. cities – Baltimore, Md.; Minneapolis, Minn.; Burlington, N.C.; and Philadelphia, Pa. Experiences from these four communities indicate that small store interventions face a variety of challenges that impact feasibility, acceptability, and long-term success. Particularly challenging issues included: understanding and accommodating the complex dynamic between program staff, store owners/managers, and customers; choosing appropriate interventions that met the needs of each community; balancing sustainability with the need for ongoing support; and identifying effective mechanisms for sharing successes and lessons learned. Lessons learned across seven thematic areas are discussed in detail. The authors conclude that while increasing access to healthy foods in small stores is viable, interventionists and researchers working in this area must focus as much effort on increasing customer demand for healthy products as they do on improving store supply of these products for such interventions to be successful.