Agricultural practices affect arthropod communities and, therefore, have the potential to influence the activities of arthropods. We evaluated the effect of cover crop species and termination timing on the activity of ground-dwelling predatory arthropods in a corn-soybean-wheat rotation in transition to organic production in Pennsylvania, United States. We compared two cover crop treatments: 1) hairy vetch (Vicia villosa Roth) planted together with triticale (×Triticosecale Wittmack) after wheat harvest, and 2) cereal rye (Secale cereale Linnaeus) planted after corn harvest. We terminated the cover crops in the spring with a roller-crimper on three dates (early, middle, and late) based on cover crop phenology and standard practices for cash crop planting in our area. We characterized the ground-dwelling arthropod community using pitfall traps and assessed relative predation using sentinel assays with live greater waxworm larvae (Galleria mellonella Fabricius). The activity density of predatory arthropods was significantly higher in the hairy vetch and triticale treatments than in cereal rye treatments. Hairy vetch and triticale favored the predator groups Araneae, Opiliones, Staphylinidae, and Carabidae. Specific taxa were associated with cover crop condition (e.g., live or dead) and termination dates. Certain variables were positively or negatively associated with the relative predation on sentinel prey, depending on cover crop treatment and stage, including the presence of predatory arthropods and various habitat measurements. Our results suggest that management of a cover crop by roller-crimper at specific times in the growing season affects predator activity density and community composition. Terminating cover crops with a roller-crimper can conserve generalist predators.