This study aims to explore the potential use of digital technology for supporting outdoor mathematics teaching and learning process. A study with explorative research approach were conducted in Indonesia. A portal and a mobile app for math trail program was created and several math trail tasks were designed around the city and uploaded into a system by the teachers. Then students run the activity by the help of mobile app to find and solve mathematical modelling tasks around the city. Data were gathered by means of participatory observation, interviews, questionnaires, and worksheets. The findings indicate that a meaningful digital technology-supported mathematical outdoor activity was successfully designed and implemented. The use of digital technology has the potential to support teachers in facilitating outdoor mathematics teaching and learning process. Students gained mathematical experiences and their performance in mathematics have improved. Further studies are essential for project development and implementation in other cities with different situation and different aspects of study.