Watershed stewardship programs succeed when intended users progress from awareness to participation. This study applies diffusion of innovations theory to five forestry, agricultural, and economic viability programs administered by the Watershed Agricultural Council in the New York City watershed. These five programs are voluntary and intended to support water quality and community vitality on working lands. A survey of nonindustrial private farm and forest landowners measured awareness, participation, and satisfaction across the watershed programs. Awareness was limited and participation was rare, yet nearly all participants reported high satisfaction, indicating an entry bottleneck at the awareness-to-participation stage. Logistic regression and generalized estimating equations models showed higher participation among landowners with larger acreage. The study recommends strengthening existing extension and outreach to better communicate programs’ relative advantages and increase observability through peer examples and targeted messaging to improve enrollment among eligible landowners.