The “Grain Belt,” “America’s Breadbasket,” “The Heartland.” The Midwest is rooted in its agricultural identity. These terms evoke the decades of labor and generations of farmers that shaped this landscape according to its agricultural potential. But the next generation of would-be farmers face nearly insurmountable obstacles that threaten farm viability and rural livelihoods in the region. Farm expansion and industrialization, changing market structures, farm debt, and ever-decreasing profit margins have long fueled farm consolidation, depopulating agricultural landscapes and rural communities. Now, development pressures and the rising cost of farmland are making access to affordable land a prohibitive barrier for young and beginning farmers. Only large and expanding farms with generations of accumulated equity can afford land, exacerbating these trends. This essay analyzes how Midwestern land trusts, nonprofits, and investment groups can help the small and mid-level farmer access or acquire land, and thereby repopulate and strengthen agricultural communities and economies. While public and private “land access” strategies have matured in the Northeast, land access efforts in the Midwest are nascent and require renewed conversation. Using case studies to ground the analysis, I explore three alternative models that address land access issues in the Upper Midwest. Due to the unique challenges present in the region, I posit that a diversity of strategies and partnerships will be necessary to establish the next generation of farmers on the land. However, land access work is part of a broader discussion of the food system. In addition to the strategies presented, state and federal policy initiatives, social justice efforts, and community buy-in, are necessary to encourage farmland succession and tenure dynamics in the Midwest that support small and mid-level farmers and enliven rural communities.