Had some friends (one friend and a friend of that friend really) who went east to west around then. We thought they were crazy for fighting the prevailing winds and the escalating terrain.

They went to Alaska, had some fun times with Canadian customs for not following directions. And they thought they took an excess of spare inner tubes and made it about halfway before needing to buy more.

My Indiana comment was more a “people from the Midwest will take any opportunity to make fun of Iowa, and if that’s not an option, make fun of Indiana or Wisconsin”

Southern Indiana has lots of hills and forested areas, including the Hoosier National forest. The Great American Rail-Trail mostly goes through the upper third of the state, however, so you miss that and are mostly in the corn belt section of the state. Its very flat and mostly farm land. Which is likely why the railways were built on that route anyways.

I personally can find flat farmland quite beautiful, but I can imagine biking through it for days might get dull.