So you want to make a little personal/single-user web-app that does not require access to the web, can be placed in a USB drive and run from PC to PC What can be done.
I decided to try my hand at this little task with a Python+CherryPy+SQLite stack. I am not going to test this on Linux today so the following is written from a windows perspective...
Lets take a common little riddle and encode it into a little game.
The Fox, then Chicken, and Grain...