This study examined the effect of crop rotations and winter cover crops (CCs) on near‐surface pore characteristics of a silty clay loam soil in a 27‐yr no‐till field experiment. The crop rotation treatments included a 2‐yr corn (Zea mays L.)–soybean [Glycine max L. (Merr.)] (CS) rotation and a 4‐yr corn–soybean–oat (Avena sativa L.)–winter wheat (Triticum aestivum L.) (CSOW) rotation. The subplot treatment was CC and no‐CC (fallow). Intact soil cores (7.62 by 7.62 cm) were extracted from each treatment in July 2018 from soybean plots and examined for X‐ray computed tomography (CT)‐measured pore parameters and other soil physical and hydrological properties. Data showed that, compared with fallow, the CC reduced bulk density (ρb) by 6% and increased saturated hydraulic conductivity (Ksat) and water infiltration rate (qs) by 1.5 times. Soils under CSOW rotation had 16, 14, and 4% higher values of soil organic carbon (SOC), total nitrogen (TN), and wet aggregate stability (WAS) compared with those under CS rotation, respectively. The CSOW rotation significantly (P 1,000 μm diameter), coarse mesopores (226–1,000 μm diameter), macroporosity, and mesoporosity compared with the CS system. The CT‐measured total porosity, number of macropores, and macroporosity were 43, 34, and 60%, respectively, higher with CC as compared to the fallow plots. The CT‐measured pore parameters were well correlated with soil ρb, Ksat, qs, SOC, TN, and WAS. This study emphasizes that cropping systems that include diverse crop rotations (CSOW) and CC has potential to enhance SOC, pore characteristics, and associated physical and hydrological properties.