For the past year and a half, my department, Academic Technology Services, has been working on a mapping project that we call Cityscapes. It's a “Web 2.0” tool to allow students to collaborate in their studies of urban neighborhoods, where geography should be an organizing theme. Think of Google Maps, then think of groups of students adding their own location markers and decorating them with photos, videos, and blogs.
The two sites we've created so far can be seen here:
http://www.ats.amherst.edu/tokyodemo
http://www.ats.amherst.edu/parisdemo
The Tokyo site is not completely open due to copyright considerations; if you would like an account, contact me.
My part of this project was preparing the historical maps that you see in the image below. This included georeferencing them but also turning them into properly positioned Google tiles.

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Yet Another Talk
My lightning talk from UMass' Information and Communications Technology Summit on 3/31/2001, a variant of the first presentation above , can be found here