Agricultural production is fraught with risks and uncertainties. However, unlike conventional agriculture, where producers have a variety of options to mitigate risks around diseases, pests, and poor-quality soils, organic farmers face limitations on the use of synthetic chemicals and fertilizers. These challenges have contributed to the low adoption of certified organic production particularly in the Lower Midwest and Mid-South of the U.S. as compared to other parts of the country, such as the Upper Midwest and Northeast. Recently, there has been growing interest in entrepreneurship and innovations happening in the agricultural sector, but our literature review revealed that there is limited research on entrepreneurship and innovations among certified organic farmers, particularly in the Mid-South region, including the states of Arkansas, Kentucky, Missouri, Oklahoma, and Tennessee. In this paper, we employed a hybrid thematic analysis, integrating both deductive and inductive approaches, to examine the entrepreneurial innovations used by certified organic farmers to address regional-specific challenges affecting their operations. We used Schumpeter’s perspective on innovations to categorize farmer innovations. Our findings reveal that farmers have demonstrated remarkable proactivity and innovativeness in tackling regional production challenges. They have done so by diversifying their products and services, improving production processes, creating new marketing strategies, and reinventing their farming. Through these approaches, farmers have created fresh opportunities for their enterprises. However, despite significant individual farmer innovations, there are system challenges for these producers. Our findings suggest an entrepreneurial ecosystems approach might be necessary to support producers’ entrepreneurial innovations, which could involve developing supportive policies and community support networks in these regions. Additional research is needed to gain a deeper understanding of the reinventions and transformations occurring among organic producers, including their experiences pushing them away from certified organic production.