The simplification of agricultural landscapes, particularly in the United States (US), has contributed to alarming rates of environmental degradation. As such, increasing agrobiodiversity throughout the US agri-food system is a crucial goal toward mitigating these harmful impacts, and crop diversification is one short-term mechanism to begin this process. However, despite mounting evidence of its benefits, crop diversification strategies have yet to be widely adopted in the US. Thus, we explore barriers and bridges to crop diversification for current farmers, focused on the Magic Valley of southern Idaho-a region with higher crop diversity relative to the US norm. We address two main research questions: (1) how and why do farmers in this region enact temporal and/or spatial strategies to manage crop diversity (the present) and (2) what are the barriers and bridges to alternative diversification strategies (the imaginary)? Through a political agroecology and spatial imaginaries lens, we conducted and analyzed 15 farmer and 14 key informant interviews between 2019 and 2021 to gauge what farmers are doing to manage crop diversity (the present) and how they imagine alternative landscapes (the imaginary). We show that farmers in this region have established a regionally diversified landscape by relying primarily on temporal diversification strategies-crop rotations and cover cropping-but do not necessarily pair these with other spatial diversification strategies that align with an agroecological approach. Furthermore, experimenting with and imagining new landscapes is possible (and we found evidence of such), but daily challenges and structural constraints make these processes not only difficult but unlikely and even "dangerous" to dream of. Therein, we demonstrate the importance of centering who is farming and why they make certain decisions as much as how they farm to support agroecological transformation and reckoning with past and present land use paradigms to re-imagine what is possible. Supplementary Information: The online version contains supplementary material available at 10.1007/s13593-022-00833-0.