Extensive summer grazing is a dairy herd management practice frequently adopted in mountainous areas. Nowadays, this activity is threatened by its high labour demand, but it is fundamental for environmental, touristic and economic implications, as well as for the preservation of social and cultural traditions. Scarce information on the effects of such low-input farming systems on cattle health is available. Therefore, the present case study aimed at investigating how grazing may affect the health status of dairy cows by using milk traits routinely available from the national milk recording scheme. The research involved a dairy herd of 52 Simmental and 19 Holstein × Simmental crossbred cows. The herd had access to the pasture according to a rotational grazing scheme from late spring up to the end of summer. A total of 616 test day records collected immediately before and during the grazing season were used. Individual milk yield was registered during the milking procedure. Milk samples were analysed for composition (fat, protein, casein and lactose contents) and health-related milk indicators (electrical conductivity, urea and β-hydroxybutyrate) using mid-infrared spectroscopy. Somatic cell count (SCC) and differential SCC were also determined. Data were analysed with a linear mixed model, which included the fixed effects of the period of sampling, cow breed, stage of lactation and parity, and the random effects of cow nested within breed and the residual. The transition from barn farming to pasture had a negative effect on milk yield, together with a small deterioration of fat and protein percentages. Health-related milk indicators showed a minor deterioration of the fat to protein ratio, differential SCC and electrical conductivity, particularly towards the end of the grazing season, whereas the somatic cell score and β-hydroxybutyrate were relatively constant. Overall, the study showed that, when properly managed, pasture grazing does not have detrimental effects on dairy cows in terms of udder health and efficiency. Therefore, the proper management of cows on pasture can be a valuable solution to preserve the economic, social and environmental sustainability of small dairy farms in the alpine regions, without impairing cows’ health.