Objective: In Japan, all medical insurers are obliged to conduct annual specific health checkups. These checkups are part of the National Health Service system and target all insured people aged 40–74 years and aim to facilitate prevention and early detection of atherosclerosis-related diseases such as hypertension, diabetes, and dyslipidemia. However, the participation rate in specific health checkups is low in Japan, especially among middle-aged community residents with municipal National Health Insurance (NHI). Additionally, previous studies suggested that those in the precontemplation stage were at higher risk for non-participation in health checkups. Therefore, this study explored the factors related to participation in specific health checkups among middle-aged Japanese community residents with NHI in the precontemplation stage. Design and Method: This cross-sectional mail survey was conducted in 2020 that involved all community residents with municipal NHI aged 40–64 years in five cities in three areas of A Prefecture, Japan. This survey included 33,902 community residents, and 12,446 (36.7%) agreed to participate in the survey. After selecting those without missing data (n = 11,180) and those in the precontemplation stage, the analysis included 2,892 participants. Participants were classified into a participation group and a non-participation group. Those who selected “I underwent a specific health checkup in the past year” were classified as the participation group. The study protocol was approved by the Institutional Review Boards. Informed consent was obtained from all participants who were included in this study. Results: In this study, 994 (34.4%) participants were classified in the participation group, and 1,898 (65.6%) were classified in the non-participation group. Multivariable logistic regression analysis revealed factors related to participation in health checkups among those in the precontemplation stage. The factor with the highest odds ratio (OR) for participation in specific health checkups was recommendations from primary care physicians to participate in specific health checkups [multivariable-adjusted OR 3.19, 95% CI 2.45–4.15, presence of recommendations vs. absence of recommendations], followed by recommendations from public health nurses [multivariable-adjusted OR 2.07, 95% CI 1.26–3.41, presence of recommendations vs. absence of recommendations], and self-reported economic status [multivariable-adjusted OR 1.82, 95% CI 1.48–2.24, good vs. poor]. Conclusions: In particular, recommendations from primary care physicians and public health nurses might be important factors related to participation in health checkups among middle-aged Japanese community residents with NHI in the precontemplation stage.