This study aims to develop learning media based on Math City Map with the context of the SMP Negeri Air Lesing school environment on congruence and similarity material and to determine the media quality based on validity, practicality, and the improvement of student learning outcomes. This study used the Research and Development (R&D) method with the ADDIE model consisting of Analysis, Design, Development, Implementation, and Evaluation. Validation involved three experts: content expert, media expert, and language expert. Validation results showed that the media was in the very valid category, with percentage scores of 86.66% from the content expert, 86.15% from the media expert, and 97.14% from the language expert. Media practicality based on teacher and student responses reached 90.66% and 92.22% respectively, both falling into the very practical category. A trial involving 26 students showed an increase in average learning outcome scores from 26.38 in the pretest to 71.23 in the posttest. These results indicate that the use of media in the research trial context was accompanied by an improvement in learning outcomes in the moderate category. The implication of this study suggests that Math City Map-based learning media can serve as an alternative for teachers in applying contextual mathematics learning through the utilization of the school environment as a learning resource for congruence and similarity topics
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