This article explores the challenges and opportunities that accompany efforts on the ground to nurture innovation as we promote stewardship, preserve valued places, advance education, and facilitate citizens’ connection to their parks and historic sites in the second century of the National Park Service. Using the first nationally designated historic site, Salem Maritime, as a case study, we examine efforts to grapple with bureaucratic inertias, entrenched patterns of insularity, and reliance on top-down authority. Support from leadership is necessary to allow education and interpretation staff on the ground to invite scholars, teachers, school districts, community educators, park neighbors, and others to participate in developing more engaged, complex, multivocal, and democratic histories and a broader vision for the new century in the NPS.