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This geography-related website addresses much more than transportation. It has many links to historic cartography and map collections; map skills lessons and activities; information and games on the U.S., the continents, and oceans; geography quizzes; and much more. (Thanks to Tyler for letting me know about the site!)
Coolmath-Games.com has free, challenging Map Snap games.
Check out the (mostly) free modern and historical maps online from the University of Texas. There are supposed to be more than 250,000 maps in the collection.
Seterra is a geography game with more than 100 different geography exercises. This is a free site that you can access online or download to your computer. It drills on states, countries, and capitals, but also covers provinces and territories within countries, oceans, lakes, rivers, flags, mountains, and important cities. It's a very simply designed program—click to assign a label to the correct location. Labels sometimes overlap each other, making it difficult to use, but it's still very good for a free resource.
Sheppard Software has some great geography games for both the U.S. and the world. These are free and quick to access, and they are especially good for practice identifying states and capitals as well as countries and their capitals.
Take a Seat Road Trip Geography is an Internet page that has links to geography and mapping resources. These include lesson material, games, maps, quizzes, and more on both World and U.S. Geography.
This website for yacht sales has a page with some fun and free geography games and quizzes.
World Geography, Cartography and Mapping Skills for Transportation is a page with a huge number of links to resources to help build geography knowledge and mapping skills.
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