To open new markets, some farmers have adapted direct-to-consumer (DTC) models, such as Community Supported Agriculture (CSA), to reach new settings or audiences. We compared sociodemographic and geospatial contexts to farmers’ experience with one of two DTC innovations: a cost-offset CSA for low-income families and food boxes distributed through rural convenience stores. We geocoded addresses of thirteen farms and DTC pickup sites in two U.S. states (Vermont and Washington) and calculated road network distances from pickup to supermarket, farmers’ market, and farm. We compiled Census block-level demographic and transportation data, and compared it to postseason interviews to explore the effect of suitability of the pickup location; proximity to food retail; and potential farmer burden. Most pickup areas were heavily car-dependent, with low walkability and few public transportation options. Conventional sources of fresh produce were within six miles of most pickups, but farmers markets were further away. Despite modest profitability, both models were deemed worth pursuing, as they expanded farmers’ customer base. Farmers implementing the store-distributed food box were sensitive to market trends and customer needs in choosing pickup location. Farmers seemed more concerned with marketing in convenience store settings, and finding efficient ways to conduct recordkeeping than with delivery distances.