Recreational activities are found to increase people’s smiles, arising joy in older people, but there is limited research on this topic within the Japanese context. This cross-sectional study aimed to measure the quality and frequency of smiles in older people living in rural settings using a smile analysis application. The participants comprised 13 females aged over 65 years who lived in Unnan City, Japan, and regularly attended recreational meetings. In this study, the recreational activity that the participants joined was a game called Mattoss. A video camera captured the participants’ faces, while a smile assessment application assessed their facial expressions for smiles and joy. A total of 2767 smiles were recorded. For validity, we calculated the Spearman’s rho score between smile and joy, which was 0.9697 (p < 0.001), while for reliability, we determined the Spearman’s rho score for each participant, which exceeded 0.7 (p < 0.001). Surges of smiles were induced by one’s own mistakes, successes, and big mistakes in the game and by severe or mild judgments by the referee. High validity and reliability of smile evaluation were demonstrated. The study found that smiling increased during recreational activities. Therefore, recreational activities can be encouraged for older people living in rural communities.