Farming is widely regarded as a highly stressful occupation, and many farming stressors have been studied globally. Research on farming stressors in Canada is scarce, yet there is some indication that Canadian farmers have high perceived stress scores and score more severely across mental health outcomes compared to the general population. This study provides a comprehensive exploration of farming stressors in Canada with the aim to inform avenues to reduce stress and/or boost the well-being of farmers. An exploratory sequential mixed-methods design was used. First, qualitative data were collected from 75 in-depth interviews with farmers and industry professionals from Ontario, Canada from 2017 to 2018. These data were then used to inform items measuring self-reported stress across 12 farming stressors in a national cross-sectional survey of farmers’ mental health conducted February–May 2021. Results from both data sources provide an initial understanding of the episodic and chronic stressors faced by farmers in Canada, and the context within which these stressors are experienced. Implications and focus areas for stress reduction and well-being promotion are discussed in this paper.