This essay is focused on the story of an old growth forest preserve in Cornwall, Connecticut known as the Cathedral Pines. The author, who grew up beside the forest, looks at the lifecycle of the forest as a case study in settler constructions of forests, conservation, and the American landscape. The author uses archival research and outreach to local indigenous and environmental activists to explore the social and ecological processes that have shaped the Cathedral Pines, within broader regional histories. The text looks at the political economic history and symbolism attached to white pine trees to explore the impacts of racial colonialism on the present ecology of forests within the Housatonic and Hudson River valley regions. The author argues that settler mythologies of wilderness continue to structure discourses of conservation. The concluding sections of the text draw on decolonial discourses of “reciprocity” to think about the potentialities embedded in efforts to align forest restoration efforts with indigenous-led environmental justice movements.