Mark Belinsky of Digital Democracy wrote an article called Future Now: NYC’s Digital Storybook - it's about his experience working with students in New York City on a webmapping demonstration project. The students used a modified version of Ushahidi software to map ideas and resources in their community. You can check out the resulting web map as well, but Mark's article includes some great background information and analysis.
"National Geographic and ESRI have created a new program to inspire educators and community members to work together to improve student learning. People who use geography in their work can help educators and youth see the world in new ways. The GeoMentor program is designed to inspire volunteers to work with a teacher or youth club leader to help kids see, use, and do more geography in and out of classrooms."