Stream morphology is affected by changes on the surrounding landscape. Understanding the effects of urbanization on stream morphology is a critical factor for land managers to maintain and improve vulnerable stream corridors in urbanizing landscapes. Stormwater practices are used in urban landscapes to manage runoff volumes and peak flows, potentially mitigating alterations to the flow regime that drive changes in channel morphology. However, there remains a paucity of long-term studies assessing watershed-scale relationships between urbanization and effects on stream morphology where green stormwater infrastructure exists in high densities. This paper evaluates the geomorphic changes across four headwater catchments in the Chesapeake Bay Watershed over the course of >10 yr and relates these changes to urban development. Annual cross-sectional surveys conducted from 2002 to 2019 in one forested catchment, one agricultural catchment, and two treatment catchments were used to understand the relationship between urbanization and changes in stream morphology. Six cross-sectional geomorphic metrics were calculated and compared with development timelines and high flow events. A channel evolution model was then used to understand the status of morphologic stability at sites within the study. Results suggest downstream environments in developing areas are more impacted during early phases of suburban construction. Channel change during construction could be a result of sediment and erosion control efforts' limitations on preventing and controlling overland sediment mobilization or of increased discharge causing widening and thus bank-derived sediment to move to the streambed. Results demonstrate that geomorphic metrics are highly variable within a small area and are not always accurate representations of broader landscape changes but rather of the more localized environment at a specific stream segment. Despite a high density of stormwater management facilities in urban catchments, substantial alterations to cross sections were found at multiple locations in each catchment including the controls.