Defined by Merriam and Webster as, “a long narrow excavation dug in the earth,” the ditch is a ubiquitous feature of road edges and fields, sited at the ecotone of urbanity where natural and constructed systems entangle. This essay explores the concept of ditching as a tactic, both materially and metaphorically, for minimally disruptive change. Using the Black Dirt Region in New York State as a case study, the chapter examines how engagement at a very small, local scale can impact large, dynamic urban-natural systems. A history of the transformation of the Drowned Lands to the Black Dirt region examines how grass-roots drainage associations urbanized watersheds as part of the large-scale transformation of wetlands across the United States. The second half of the chapter reframes the ditch from an object into an apparatus through the concept of ‘ditching’, offering the potential to both understand and intervene in the cultural and ecological entanglements of urban regions, through a linear zone that spans the aquatic to the terrestrial to the atmospheric. This work was presented at the Minimally Invasive Urbanism Symposium, in Edinburgh, June 2023, and will be published in the forthcoming book, “Seeding Urban Transformation: Tactical Urbanism for Systemic Reparation.”