This dissertation examines the barriers to and drivers of a transition to regenerative agriculture in the US Corn Belt through bottom-up and top-down approaches to addressing change. Working closely with non-governmental organizations to develop and implement the research, I draw on surveys, interviews, focus groups, participant observation, and document analysis to explore farmer decision making in two contexts: a formal farmer network, Practical Farmers of Iowa (PFI), and in the adoption of small grains, or cereal crops such as barley, oats, rye, and wheat. In the first part of the dissertation, composed of Chapters 1 and 2, I examine the role of PFI in the adoption of a range of conservation practices among member farmers. In the second part, composed of Chapter 3, I focus on one important conservation practice — diversification through small grain production — and explore a range of factors that influence farmers’ decision making in this context. I pay particular attention to farm policy, an often-neglected element in understanding farmer decision making. Several key findings emerged from the dissertation. First, formalized peer networks of farmers can play a significant role in the adoption of conservation practices, evidenced by a large and longstanding formal farmer network, PFI. Second, in-person ways of participating in networks like PFI can have a greater impact on the adoption of conservation practices compared to independent formats due to the ability to have side conversations with other farmers, ask questions, and observe results. Third, PFI has created a recipe for collaborative, farmer-driven research that relies on a diverse membership, autonomous functioning, culture of openness, and non-ideological nature. Fourth, when considering one specific conservation practice, the adoption of small grains, a multitude of factors influence farmers’ decision making; markets are the most important, and the specific Farm Bill programs available for small grains are comparatively less important. Just as there are a multitude of factors that impact farmer decision making, there are a multitude of actions that must be taken to support farmers to transition to regenerative agriculture including market development and processing infrastructure for a diverse array of farm products, sourcing commitments from food companies to purchase local products grown using conservation practices, improved varieties and practices for conservation agriculture, risk management tools and cost share that incentivize diversification, and peer support and education on alternative practices through farmer networks.