Check out this map generator I discovered - it has you fill out all the states you have visited, and the colors coordinate to how familiar you are with that state:
Red means I've just passed through, maybe seen a thing or two.
Amber means I've at least slept there and seen a few things. I have a first-hand idea of what the state is like.
Blue means I've spent a good amount of time in that state.
Green means I've spent a lot of time in that state, weeks at at time on multiple visits – or lived there.
As you can tell, I've basically only seen the middle of the USA, with a little of the north eastern coast. :) You can make one with just the US, or one with the US and Canada.
Visit the webpage here: http://www.defocus.net/visitedstates/ to make your own! If you do make one and post it somewhere, leave a link for me in the comments!