In 2020, a mobile application (app) was developed to connect small food retailers with local producers, recognizing the underutilization of direct-to-retail sales channels. Before piloting the app, formative research was conducted in Charles County, Maryland, to gain an understanding of existing direct-to-retail sales channels for locally grown produce. Seven stores were surveyed to explore current local produce stocking, and four farmers participated in in-depth interviews to provide insights into their experiences with direct-to-retail marketing channels. The results indicate a limited stocking of local produce in the small food stores, some of which was self-procured to obtain adequate quantities. Farmers expressed a passion for contributing to food security in their community and a willingness to collaborate with store owners to strengthen their direct sales; however, they cited barriers such as the impact of the COVID-19 pandemic, competition with large distributors, and logistical challenges. Considering these existing barriers and facilitators, small food stores may still possess a unique potential to establish direct sale relationships with local farms. Such relationships could be effectively facilitated through the implementation of a digital strategy.