This study explores the motivations behind participation in tree planting programs by private landowners in Ontario, Canada, as well as perceptions as to whether benefits were realized up to ten years after trees were planted. Forests Ontario, which has offered tree planting support programs in this province since 2007, provides up to 90% of the cost of seedlings for tree planting projects at least one hectare (ha) in size. This online survey of 570 former participants in tree planting programs indicated that a desire to create a habitat for wildlife (77.6%) was the most common motivation for taking part in a tree planting program. Concern with restoring native forest cover was also a reason for most participants (71.4%), as well as with improving soil, air and water quality (54.8%), and addressing climate change (54.3%). The most common benefit of planting trees was an increase in well-being and enjoyment of their property (67% of respondents). Overall, 27% of respondents with a desire to increase wildlife habitat, and 20% of those wishing to improve their local environment reported an improvement after tree planting. Reported improvements in the local environment and wildlife increased with time since tree planting, whereas enhanced well-being and enjoyment of the property were evident among participants even with newly planted trees.