The agricultural profession, particularly dairy farming, is known for its demanding nature, both physically and mentally. Dairy farmers encounter various challenges including long working hours, physical labour, financial pressures, and unpredictable weather conditions. My objective was to explore different farm management practices, farming factors, and the prevalence of mental and physical health issues among dairy farmers in Western Canada and Ontario. Statistical analyses included t-tests, ANOVA, and chi-squared tests to compare means with general population averages and to investigate associations between mental health scores and physical health outcomes with survey variables. The results of the survey indicated that farmers (n=115) scored significantly higher on perceived stress (P<0.001), anxiety (P<0.001), depression (P=0.04), and resilience scales (P<0.001) compared to the general population. The results also highlighted concerns regarding the physical health of dairy farmers, with the majority reporting work-related injuries and health issues. I identified significant differences when comparing mental and physical health with work-life balance, social environment and support, and specific dairy-related stressors. Farmers faced both personal and farming-related financial stressors. Surprisingly, health outcomes did not differ based on housing or milking system, management practices, farm responsibilities, or financial and transition planning variables. Therefore, dairy farmers appear to have similar well-being in different production systems, but farm finance, feed cost, weather, and workload constraints are major stressors. I then adopted a more holistic approach to cluster farmers based on their well-being and farm management. The analysis identified four distinct groups of dairy farmers based on their survey responses. It also emphasized the need for a deeper understanding of the unique challenges faced by individual farmers in their production systems. Without this understanding, there is a risk of developing intervention plans that are ineffective or inappropriate for the Canadian dairy industry. The typologies developed in this research offer a promising foundation for providing tailored support resources.