This study aims to assess the compositional traits and sensory characteristics of a traditional pecorino cheese associated with management and feeding system seasonality. The study was carried out on two mountain dairy farms using an outdoor, pasture-based system from April to October (OutS), and an indoor system (InS) during the rest of the year. Outdoor-produced milk had higher fat content and a tendency for protein and somatic cell count to be higher. The OutS cheeses showed higher dry matter and fat content, higher percentages of unsaturated fatty acids, C18:3, cis-9, trans-11 conjugated linoleic acid, and trans-11 C18:1, and lower percentages of C14:0 and C16:0. These modifications in fatty acid composition determined the reduction of the atherogenic index. The OutS cheeses also displayed higher intensity of almost all sensory attributes, including odor, flavor, taste, and texture descriptors. The outdoor system partly reduced the liking of consumers for pecorino. However, changes in the productive process leading to an increment in the water content and softness of the cheeses (i.e., controlled humidity and temperature during ripening) may increase the overall liking of pasture-based products, thus promoting the consumption of healthier foods.