Considerable research has demonstrated the connections between food deserts, dietary outcomes, and chronic diseases. Less research exists on upstream challenges that could play a role in the creation and perpetuation of food deserts. This study examines barriers to supplying affordable produce to food deserts. We conducted expert interviews with channel members of a regional produce supply chain to reveal perceived supply chain barriers, which included high distribution costs, lack of perceived consumer demand, and failure to achieve scale economies. Opportunities identified included providing strategic economic incentives, improving retail infrastructure, and working with novel distribution mechanisms such as food hubs.