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Walk scores are used to evaluate accessibility by walking from a location to various meaningful destinations. Their validity remains contested because the widely available walk scores from the Walk Score® company are typically constructed using objectively measured origin–destination distances, which may be inconsistent with people’s spatial perceptions and even irrelevant to destinationless recreational walking trips. This study examines the divergency between objective walkability measured as walk score and subjective walkability assessed by perceived accessibility. Using data collected during the COVID-19 pandemic, we conducted spatial autocorrelation and multi-level regression analyses. Findings suggest that characteristics of both location and people affect the divergency between subjective–objective walkability. Regardless of their individual socioeconomic characteristics, respondents tend to match their subjective walkability assessment with the walk score better when they live in denser and older neighborhoods where more people may walk for utilitarian purposes. On the other hand, respondents with greater beliefs in environmental policies evaluate walkability in better alignment with walk score, regardless of their locational characteristics. The findings suggest that the main reasons for the subjective–objective divergency may lie in people using recreational walking for walkability assessment and their lack of lived experiences of utilitarian walking. Planners and policymakers should be mindful of the objective–subjective walkability divergency when using walk scores to support strategies and actions to improve walkability.