The multidimensional concept of animal welfare includes physical health, good emotional state, and appropriate behavior of the animals. The most recent methods for its assessment are inspired by the Welfare Quality, a project compiling animal-, resource-, and management-based measures. Recently, animal welfare assessment has also considered the human factor in a so-called “One Welfare” approach. The One Welfare framework highlights the interconnections between animal welfare, human well-being, and the environment. The concept seems to fit particularly well to mountain areas where the relationship between human, animals, and the environment is stronger. In such disadvantaged areas, farmers' well-being plays a key role in maintaining livestock farming profitably and sustainably. This study aims to investigate the relationship between farmers' satisfaction, animal welfare outcomes, and overall farm performance in 69 small-scale dairy farms in the Eastern Alps. Animal welfare assessment consisted of animal-based measures and was performed using the methodology proposed by the European Food Safety Authority for this type of farm. Moreover, the farmers were interviewed to retrieve data on farm characteristics and on their level of satisfaction toward workload, land organization, relationship with the agricultural/non-agricultural community, and the future of local agriculture. The results show that good animal welfare can be obtained in a mountain farming system. Clinical indicators show a low prevalence of diseases and of very lean cows as opposed to integument alterations. The workload is not perceived as a problem in traditional farms (i.e., tie-stall and with no participation in quality-certification schemes). Animal welfare is higher in those farms where farmers have a positive engagement with both the agricultural and non-agricultural community and where farmers are satisfied with their land organization. A One Welfare approach could be applied on a larger scale to fully understand the links between animal and human well-being in mountain areas.