Future farming systems will require more flexibility in design for application under conditions of increasing climatic fluctuations. Two potential solutions are more complex rotations, e.g. sequences of unlike crop species in the field, and multiple cropping systems that combine different crops during the same season and add spatial and/or temporal diversity to a farming system. In this review, we discuss how adaptive rotations based on alternative crops, long rotation cycles, and multi-crop systems, as well as integrated crop-livestock options could improve farm productivity, sustainability, and resilience. We also discuss potential challenges and opportunities connected to adaptive rotations. Limited literature suggests adaptive crop rotations based on present soil conditions, current soil moisture, predicted precipitation, previous crops and yields, and the latest market information may be promising for farmers. We propose that adaptive rotations could improve soil biodiversity and health, water use, pest management – including insects, pathogens, weeds and other pests, and overall agricultural resilience against climatic change. Also, adaptive rotations provide opportunities for exploring intercropping, complex rotations, and crop-livestock integrated systems, while achieving greater economic resilience for farmers. Primary forces that may impede the successful adoption of adaptive rotations include human factors (conservative reluctance to change), complexity of incorporating new options (i.e., new crops, equipment), limited land ownership, federal subsidies limited to certain commodities, risks perceived by lending agencies (about half of farmed land in the Midwest U.S. is leased), and lack of research results. However, increasing market uncertainties, emerging focus on soil health, and growing concerns about climatic fluctuations represent ample incentives to pursue adaptive rotations in different agroecoregions. We conclude that adaptive rotations would open new options for farmers to seek sustained profits in unpredictable and rapidly changing economic and weather environments.