Dryocopus pileatus (Pileated Woodpecker) is an endemic North American woodpecker that, following widespread declines during the mid-to-late 19^th century, rebounded and has become relatively common resident throughout its range. In New York City, Pileated Woodpeckers were breeding residents until the early to mid-1800s, but were extirpated due to the city's rapid urbanization. Since the 1930s, however, the number of reports of Pileated Woodpeckers has increased dramatically in the area. Here we document the re-establishment of Pileated Woodpeckers in New York City within 2 old-growth greenspaces on Staten Island from 2015 to 2019. We further describe and validate a previously unpublished breeding attempt on Staten Island from 1989. The establishment of Pileated Woodpeckers in New York City is reflective of their ongoing colonization of urban and suburban areas throughout North America, and highlights the importance of unfragmented greenspaces within urban and suburban areas.