I think google maps api is a good place to start. [whether you use python, or javascript ]
Drawing state lines seems to be automatic. Coordinates are visible on maps.google.com. (might need to click labs) Creates images when zooming in/out. Not sure if clicking on a region is automatic, but looks addable. [ since state region polygon info is below ] On click, do point vs polygon collision detect. I just saw a offline-googlemap viewer in python, but can't find the link. You had to view it once, but then it can save it. [ so users might not need net, if you generate the cache? ] Look at this: ( drawn state outline, you drag it onto its real location ) http://maps.forum.nu/gm_place_that_state.html [ toc: http://maps.forum.nu/ ] Some links I found searching: pygame - python game development http://www.pygame.org/project-pyMap+Explorer-1433-.html How to use overlay the state on the map with different color? - Google Maps API | Google Groups http://groups.google.com/group/Google-Maps-API/browse_thread/thread/01711c0f5f1d0fdd Shapefile Tiles with PHP and GD at Beginning Google Maps Applications http://www.googlemapsbook.com/2006/09/09/shapefile-tiles/ State Outline - Google Maps API | Google Groups http://groups.google.com/group/Google-Maps-API/browse_thread/thread/c210100bda02c5ef?hl=en Census 2000: State and State Equivalent Areas Cartographic Boundary Files - U.S. Census Bureau http://www.census.gov/geo/www/cob/st2000.html Importing Shapefiles at Beginning Google Maps Applications http://www.googlemapsbook.com/2006/08/30/shapefiles/ geopy - Project Hosting on Google Code http://code.google.com/p/geopy/ GettingStarted - geopy - A quick-start guide to geopy. - Project Hosting on Google Code http://code.google.com/p/geopy/wiki/GettingStarted -- Jake