Inspiration: I am not that smart to come with an original idea like this one. I came across a tweet by Professor that said that he had asked his students to come up with an ugly USA map and he tweeted the image. I wanted to do something very similar. The link to the professor site : http://www.brenthecht.com/
Tile Mill: The image was created using tile mill an open source project by Mapbox. Its free to download and the documentation is very well written. Its a great tool to quickly generate graphs. It took me like 2 hrs to come up with the image posted above. This image is very similar to what the professor had tweeted.
I will try to write a small introduction on step by step instructions on creating this UGLY map. But if you are curious to learn may be this link will help you get started .
Off course similar things can be done using R. Somehow i think Tile mill is easy to learn and very handy. If you like to play with maps, data and not great at coding then this is a great tool for you.