Ground beetles (Carabidae) are beneficial insects providing ecosystem services by regulating insect pests and weed seeds. Despite several studies conducted on ground beetles worldwide, there is a lack of knowledge on how these insects are affected by differently managed organic systems (e.g., tillage-based versus grazed-based) compared to that of chemical-based no-tillage conventional cropping systems. In a 5-year (2013–2017) study, we assessed the ground beetle communities in cover crops and winter wheat (Triticum aestivium L.) in Montana, USA, with three contrasting cropping systems: a chemically managed no-tillage, a tillage-based organic, and a livestock-integrated organic with reduced tillage. The first three years (i.e., 2013–2015) corresponded to the transition to organic period, while the last two (i.e., 2016–2017) were conducted in United States Department of Agriculture (USDA) organic-certified tillage-based and livestock-integrated organic systems. The experiment was designed with three management systems across three blocks as the whole plot variable and 5-year rotation of crop phases as the subplot variable. Using pitfall traps, we sampled ground beetles across all cover crop and winter wheat subplots for five years (n = 450). The data were analyzed using mixed effects models and PERMANOVA and visualized with non-metric multidimensional scaling ordination. Our study indicated that organically managed farms, whether tilled or grazed, enhance activity density, species richness, diversity, and evenness of ground beetles in the dryland row crop productions. Also, irrespective of farming system, cover crops supported higher species richness, diversity, and evenness of ground beetles than winter wheat. The ground beetle communities were mostly similar during the transition to organic period. However, during the established organic phase, cropping systems acted as contrasting ecological filters and beetle communities became dissimilar. Cover cropping affected ground beetle communities positively not only in organically managed systems but also in chemical-based conventional systems. Our study provides evidence supporting the adoption of ecologically-based cropping systems such as crop-livestock integration, organic farming, and cover cropping to enhance beneficial insects and their pest-regulation services.