Objectives: The Coronavirus disease 2019 (COVID-19) pandemic disrupted medical student education, particularly in New York City (NYC). We aimed to assess the impact of the COVID-19 pandemic on medical students’ residency choices. Methods: The authors conducted a cross-sectional survey of medical students in all years of study at four NYC medical schools (Columbia, Cornell, NYU, and SUNY Downstate). The survey was fielded from 19 Aug 2020 to 21 Sep 2020. Survey questions included items assessing COVID-19 impact on residency choices, personal impact of COVID-19, residency/specialty choices, and factors influencing these choices. Results: A total of 2310 students received the survey, with 547 (23.7%) providing partial responses and 212 (9.2%) providing valid responses for our primary analysis. 59.0% of participants thought that COVID-19 influenced their choice of residency/specialty, with 0.9% saying the influence was to a great extent, 22.2% to some extent, and 35.8% very little. On multivariable analysis, factors that were independently associated with COVID-19 impacting residency choice included low debt ($1 to $99,999: adjOR 2.23, 95%CI 1.02–5.03) compared with no debt and Other race/ethnicity (adjOR 0.26, 95%CI 0.10–0.63) compared with White race/ethnicity. On secondary analysis of all participants answering survey items for logistic regression regardless of survey completion, direct personal impact of COVID-19 was significantly associated with COVID-19 impacting specialty choice (adjOR 1.90, 95%CI 1.04–3.52). Moreover, 24 students (11.6%) reported a change in their top residency choice from before to during/after COVID-19, citing concerns about frontline work, work-life balance, and risk of harm. Conclusions: Our study found that 3 in 5 (59.0%) participants felt that COVID-19 impacted their residency choice, with 11.6% of respondents explicitly changing their top specialty choice. Investigating the impact of the pandemic on medical student residency considerations is crucial to understand how medical career outlooks may change in the future.