Background: In 2019, the World Health Organization identified vaccine hesitancy as a top ten global health threat, which has been exacerbated by the COVID-19 pandemic. Despite local and nationwide public health efforts, adolescent COVID-19 vaccination uptake in the US remains low. This study explored parents’ perceptions of the COVID-19 vaccine and factors influencing hesitancy to inform future outreach and education campaigns. Methods: We conducted two rounds of individual interviews via Zoom in May–September 2021 and January–February 2022, with parents of adolescents from the Greater Newark Area of New Jersey, a densely populated area with historically marginalized groups that had low COVID-19 vaccination uptake. Data collection and analysis was guided by the Increasing Vaccination Model and WHO Vaccine Hesitancy Matrix. Interview transcripts were double-coded and thematically analyzed in NVivo. Results: We interviewed 22 parents (17 in English, 5 in Spanish). Nearly half (45%) were Black and 41% were Hispanic. Over half (54%) were born outside of the US. Most of the parents described that their adolescents had received at least one dose of a COVID-19 vaccine. All but one parent had received the COVID-19 vaccine. Despite strong vaccination acceptance for themselves, parents remained hesitant about vaccinating their adolescents. They were mostly concerned about the safety and potential side effects due to the novelty of the vaccine. Parents sought information about the vaccines online, through healthcare providers and authorities, and at community spaces. Interpersonal communication exposed parents to misinformation, though some personal connections to severe COVID-19 illness motivated vaccination. Historical mistreatment by the healthcare system and politicization of the vaccine contributed to parents’ mixed feelings about the trustworthiness of those involved with developing, promoting, and distributing COVID-19 vaccines. Conclusions: We identified multilevel influences on COVID-19 vaccine-specific hesitancy among a racially/ethnically diverse sample of parents with adolescents that can inform future vaccination interventions. To increase vaccine confidence, future COVID booster campaigns and other vaccination efforts should disseminate information through trusted healthcare providers in clinical and also utilize community settings by addressing specific safety concerns and promoting vaccine effectiveness.