Environmental stewardship is increasingly important as human actions threaten the natural world. Now, more than ever, it is necessary to understand what makes stewardship initiatives successful. This study investigates stewardship success in the Niagara Region of Ontario, Canada. Specifically, the research seeks to determine what factors are associated with the success of environmental stewardship initiatives, differences between stewardship organizations (staff-based vs. volunteer-based), and reasons why those factors are important. Ten factors for successful stewardship initiatives were uncovered. Differences between volunteer and staff-based organizations were revealed, especially regarding factors of motivations and capacity. Qualitative analysis provided rich insights into why factors were important for success, with the physical ability to conduct the work and the importance of motivation being highlighted. The findings from the study provide a basis for future research which expands the empirical contexts for understanding stewardship success, broadens the variety of stewardship organizations considered, and incorporates additional measures of success.