The COVID-19 pandemic and associated public health measures have interrupted the daily routines of parents and children. The purpose of this study was to explore parents’ attitudes regarding their children’s play/sport during COVID-19. A secondary objective was to explore the influence of parent demographics and parent-reported physical activity levels and risk tolerance on these attitudes. Ontario parents of children aged 12 and younger completed an online survey (August—December 2020) that assessed their attitudes (grouped by support, safety and socialization-related attitudes; n = 14 items) regarding their child(ren)’s play/sport, their physical activity levels (n = 2 items), and demographic details (n = 16 items). Two open-ended items were used to gather a deeper understanding of attitudes. Parents’ tolerance for risk was measured via the validated Tolerance of Risk in Play Scale. Descriptive statistics were calculated to describe attitudes and risk tolerance. Least Absolute Shrinkage and Selection Operator regressions were conducted to examine factors influencing parents’ attitudes. Multiple linear models were computed using the identified predictors for each attitude category. Deductive content analysis was undertaken on open-ended responses. Participants (n = 819) reported the highest scores for safety-related attitude items (M = 3.54, SD = .63) followed by socialization and support, which all influenced attitudes regarding children’s play/sport (p < .05). Demographics and parents’ physical activity levels were identified as important predictors of parents’ attitudes. Qualitative data revealed that parents had mixed levels of comfort with respect to their children’s return to play/sport. Findings from this study reveal that increased support is needed to guide future play/sport decision-making.