Background/Objectives: Despite growing interest in oral frailty as a public health issue, no nationwide study has assessed regional differences in oral frailty awareness, and the factors associated with such differences remain unclear. This study investigated regional differences in oral frailty awareness among older adults in Japan and identified the associated individual- and municipal-level factors, focusing on local policy measures and community-based oral health programs. Methods: A cross-sectional analysis was conducted using data from the 2022 wave of the Japan Gerontological Evaluation Study. The analytical sample comprised 20,330 community-dwelling adults aged ≥65 years from 66 municipalities. Awareness of oral frailty was assessed via self-administered questionnaires. Individual- and municipal-level variables were analyzed using multilevel Poisson regression models to calculate prevalence ratios (PRs). Results: Awareness of oral frailty varied widely across municipalities, ranging from 15.3% to 47.1%. Multilevel analysis showed that being male (PR: 1.10), having ≤9 years (PR: 1.10) or 10 to 12 years of education (PR: 1.04), having oral frailty (PR: 1.04), and lacking civic participation (PR: 1.06) were significantly associated with lack of awareness. No significant associations were found with municipal-level variables such as dental health ordinances, volunteer training programs, or population density. Conclusions: The study found substantial regional variation in oral frailty awareness. However, this variation was explained primarily by individual-level characteristics. Public health strategies should focus on enhancing awareness among socially vulnerable groups—especially men, individuals with low educational attainment, and those not engaged in civic activities—through targeted interventions and community-based initiatives.