This study integrates volunteered geographic information (VGI) into GIS and contextual analyses, and develops a framework to evaluate students' understanding of "locations and places in order to set national and international events within a geographical framework and to understand basic spatial relationships" as proposed by the Commission on Geographical Education (CGE). A web-based VGI was developed to allow students to share events taking place in the locations and places around the world. Three approaches are conducted to analyze all VGI records. First, GIS analysis shows the spatial pattern of VGI records and revealed students' mind map. Second, contextual analyses show students' preferences in certain geographic issues. Third, tag-cloud technology reflects students' spatial literacy based on the frequency of spatial-related terms. The results conclude that this study brings to the reader the exciting possibility of VGI and tag-cloud technology in allowing educators to evaluate students' spatial understanding and, ultimately, contributes to the future development of geography education.