Amid a decline in public awareness of local communities, there is increasing interest in encouraging people to make new discoveries in their surroundings. By prompting users to focus on real-world information rather than relying solely on their devices, the system offers opportunities to notice aspects they may typically overlook and gain new insights into the local area. One effective method for promoting real-world observation is the use of highly visible landmarks. Against this backdrop, this study developed a system to support strolling by leveraging such landmarks. The system integrates web-geographic information systems (Web-GIS), a strolling support system and gamification elements to help users explore and engage with their environment. It was deployed in Chofu City, Tokyo, and operated for 40 days from December 2023 to January 2024, attracting 70 users. A subsequent online questionnaire survey with 50 respondents (valid response rate: 64.9%) indicated that while basic functions were well-received, advanced functions such as spot visits, favorite spot registration, and mission display were less favorably evaluated or underutilized. Nonetheless, overall feedback was positive, suggesting that improving user manuals could enhance the usability of advanced functions.