Hundreds of locally based watershed initiatives have mobilized stakeholders to take voluntary action to restore the ecological conditions of North America's watersheds. Lead organizations rely on project-based grant funding, alignment with government programs, and volunteerism to incrementally restore what is ultimately a vast and complex ecosystem. Structurally, the vision and goals of these initiatives often exceed available resources and capacity. In 1999, the Bonneville Environmental Foundation began to test ways by which a funder might increase the capacity of local watershed organizations to achieve long-term watershed restoration goals through a 10-year commitment of funding and technical support. We partnered with other funders, collectively seeking solutions to increase the impact of this work. Reflecting on 13 years experience across 21 watersheds in 7 western states (USA), we have concluded that the scale of ecological change desired requires a time frame for planning, implementation, and public engagement that is inconsistent with present-day approaches. This has left us asking how can the capacity and impact of a watershed initiative be sustained over many decades—a time frame that exceeds the tenure of any individual leader, the proven life cycles of many nonprofit organizations, and the commitment of most funders? Clear themes have emerged: (1) engaging diverse stakeholders in planning, (2) orienting the work around broader goals, (3) emphasizing human well-being, and (4) developing resilient partnerships. Reimagining watershed restoration in this context, we suggest a new agenda for action and research that emphasizes a multidecadal planning horizon integrating climate change projections and changing demographics and social values. WIREs Water 2017, 4:e1174. doi: 10.1002/wat2.1174 For further resources related to this article, please visit the WIREs website.