Picturesque nature and water pipe evolved in parallel in pre–Civil War New York City to unleash two powerful dimensions of today’s city: land-driven real estate—getting rid of water through good drainage—and water-driven leisure—designed to escape landed real estate. This thesis reveals the role played by one design intervention to further these mutually supportive measures: Central Park. Built around the receiving reservoir of the Croton Aqueduct, it introduced picturesque nature to the city alongside the waterworks. This language of the modern city developed in response to the epidemics and pollution associated with Manhattan’s wetlands. Collect Pond’s transformation into Five Points in downtown Manhattan is one early 19th-century case study of this type of evolution. In the face of the COVID-19 pandemic, will the new postwar city alter its picturesque nature and waterworks?