This paper proposes a novel method for dynamically extracting and monitoring the entrances of areas of interest (AOIs). Most AOIs in China, such as buildings and communities, are enclosed by walls and are only accessible via one or more entrances. The entrances are not marked on most maps for route planning and navigation in an accurate way. In this work, the extraction scheme of the entrances is based on taxi trajectory data with a 30 s sampling time interval. After fine-grained data cleaning, the position accuracy of the drop-off points extracted from taxi trajectory data is guaranteed. Next, the location of the entrances is extracted, combining the density-based spatial clustering of applications with noise (DBSCAN) with the boundary of the AOI under the constraint of the road network. Based on the above processing, the dynamic update scheme of the entrance is designed. First, a time series analysis is conducted using the clusters of drop-off points within the adjacent AOI, and then, a relative heat index ( R H I ) is applied to detect the recent access status (closed or open) of the entrances. The results show the average accuracy of the current extraction algorithm is improved by 24.3% over the K-means algorithm, and the R H I can reduce the limitation of map symbols in describing the access status. The proposed scheme can, therefore, help optimize the dynamic visualization of the entry symbols in mobile navigation maps, and facilitate human travel behavior and way-finding, which is of great help to sustainable urban development.