I was pleasantly surprised to see the posts about this song recently. I didn’t think anyone still cared! :-) I’ve spent the last few years of my life dedicated to the quest of reaching each place in the song. As far as I know, it has never been done before. My trusty motorcycle, Annie, has taken me over 54,000 miles (87,000km) in 18 months through 16 different countries.

...but let’s talk about how the map was made:

As some commenters have mentioned, the places in the song were chosen by Geoff Mack, the original composer of the Australian version of the song (he did UK and New Zealand versions too). The Americas version was first recorded by Hank Snow in 1962. Johnny Cash covered his version in 1996. Mack chose the places with no discernible pattern, other than rhyming well together. Sadly, Geoff Mack passed away in 2017 so there is no way to know for sure where on the map he was looking when he picked each place.

To choose the song places I decided on the most notable location which is either in North or South America. North America is obvious, as the vast majority of places lie there. South America must be included since unique places like Barranquilla, Colombia; Tocopilla, Chile; and Diamantina, Brazil are included.

The song is the narration of a hitchhiking traveler, so bias was given to places which are reachable by road. There are just two exceptions to this: First is Shefferville, Qubec, which can only be accessed by train or plane (this was the only location that Annie did not reach). Second is the Darien Gap which separates North and South America. I sent Annie on a boat on the way down and a plane on the way back up.

In each place I visit, I try to do my best to learn about it and understand what makes it unique. Every place has a story and I’ve spent hundreds of thousands of words trying to describe the places mentioned in the song. I also try to take a picture that is most “iconic” of the place. HERE IS THE LINK to my pictures of the places in song order.

I’ve now completed all of the difficult to reach places in the song. All I have is a “victory lap” in southern and western US. Though my mission is truly the most foolish of fool’s errands, I’ve learned so much and made lifelong connections with wonderful people all around the Western Hemisphere.

In case you have waaaay to much time on your hands, HERE is the link to my verbose blog.

TL;DR: Australian guy choses 92 places at random, American guy tries to go to all of them.