Feather pecking and cannibalism are prominent problems in modern laying hen husbandry. Among the various approaches to address this issue, environmental enrichment plays a crucial role. In this on-farm study, four winter gardens of an organic farm henhouse were equipped with an automatic enrichment device. Different quantities of downpipes dosing grain on rough-coated pecking plates (PPs) were tested. One group served as a control (CG) without an automatic enrichment device, while the others were offered different numbers of PPs, with one equipped with a doubled amount of PPs (DEG) compared to the other two groups (SEG). Video analyses of the hens’ duration of stay and behaviors in the recorded winter garden area and around the PPs were performed, and regular assessments of the plumage condition were conducted. By the end of the production cycle, no hens with intact plumage were found, with hens in the CG and DEG showing worse scores and earlier deterioration in the plumage condition than in the SEG. The offer of PPs showed a significant influence on the duration of stay in the filmed area. Hens in the DEG stayed significantly longer (mean: 129 s, SD: 126 s) than those in the CG (mean: 79 s, SD: 91 s; p < 0.05) and SEG (mean: 75 s, SD: 83 s; p < 0.005). On the performed behavioral bouts per hen and minute (CG mean bouts/minute (SD): 5.47 (2.92); SEG mean (SD): 5.33 (2.76); SEG mean (SD): 5.81 (3.24)), no significant influences were detected. Environmental pecking was the behavior most frequently observed in all winter gardens, where, particularly around the PPs, pecking at the device was observed. Therefore, the enrichment device can be assessed as well accepted by the hens in winter gardens. The effect of the device on the plumage condition remains unclear, with external factors probably showing a greater influence than the enrichment.