Road generalization is a method for thinning out road networks to allow easy viewing according to the size of the map. Most conventional road generalization methods mainly focus on the length of a stroke, which is a chain of links with good continuity based on the principle of perceptual grouping applied to network data such as roads and rivers. However, in the case of facility search in a web map service, for example, a "restaurant guide map," a road generalization mechanism can be more effective if it depends not only on the stroke length but also on the facility search results. Accordingly, in this study, we implement an on-demand road generalization method that adapts to both the facility search results and the stroke length. Moreover, a sufficiently fast response speed is achieved for practical use in web map services. In particular, this study proposes a fat-stroke model that links facility information to individual strokes and implements a road generalization method that uses this model to improve the response time. In addition, we develop a prototype based on the proposed system. The system evaluation results are based on three indicators, namely, response time of the road generalization system, connectivity between strokes, and connectivity between stroke and facilities. Our experimental results suggest that the proposed method can yield improved response times by a factor of 100 or more while affording higher connectivity.