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This paper presents data on humpback whale sightings within the New York-New Jersey Harbor Estuary (NYNJHE), a highly urbanized estuarine system adjacent to the northwest portion of the New York Bight. Fieldwork was conducted on board the American Princess, a 29 m whale-watching vessel docked in Rockaway, Queens, New York. Trip frequency varied between 1 and 16 trips per month and increased each year in seasonal scope, from June through September in 2011 to April through December in 2016. Trips were opportunistic and focused on the coastal portion of the northwestern New York Bight, and occasionally included Lower New York Bay. There were 46 humpback whale sightings in the NYNJHE between 2011 and 2016. Whales sighted during fieldwork comprised 23.9% of sightings. The remaining 76.1% were anecdotal sighting reports. Sightings were most frequent during 2016 (31, or 67.4%), and there were eight (17.4%) sightings in 2015, six (13.0%) in 2014, none in 2013, one (2.2%) in 2012, and none in 2011. There were no documented sightings during the winter months (January–March), but 6 (13.0%) sightings occurred in spring (April–June), 10 (21.7%) during summer (July–September), and 30 (65.2%) occurred during the fall (October–December). These data are consistent with the hypothesis that the increase in humpback whale sightings in the NYNJHE is a recent occurrence. Although sightings appear to be increasing, there is not yet enough data to make a determination on the cause. Continued research is needed to determine whether sightings will continue to increase or return to previous levels. If there is continued use of this area, overlap with major shipping channels and other human activity presents a potential risk to both whales and vessels. Due to the fact that large whale sightings in the NYNJHE have previously been uncommon, vessel operators and other ocean recreational users may be largely unaware, not only of their presence, but of proper whale-watching guidelines, thus increasing the risks of vessel strike and harassment. The results of this paper can be used by managers to better regulate the NYNJHE with regards to humpback whales and ocean users to prevent these negative interactions.