I get the feeling that you're ready to get out and experience what backpacking has to offer, but you're lacking any experience to plan how to do it.

I'll start by saying that if you really feel like you have to walk off and away, plan a shorter trip first. Walk to a town 30 miles away, spend the night there, and walk back. See how that goes for you.

I've driven across Iowa, Nebraska, and Colorado a few times. That's a mighty long drive, an incredibly long hike, and it's pretty boring scenery from the Mississippi to the Rockies.

One issue you have is that there is almost no public land there, and what there is offers very little in the way of camping. The distance between campsites could easily span 100 miles or more. I don't know how you'd work around that. You could try to stealth camp, but that can get you into all kinds of crappy situations. Of course, you could consider those "Adventures", but by that definition hazard and peril are part of what you must expect.

I'm not a big fan of the "Into the Wild" story. First off, being hungry sucks big time, so does being tired, thirsty, wet, and cold. Being all of those at once really sucks. I've experienced that first hand while having plenty of time to ponder why I was in that position and what I needed to do to get out of it. The short of it is, I'd been stupid getting there and I had to work hard to get out. The lesson I learned was not to go there again.

It's one thing to take a minimalist approach to backpacking, it's quite another to take next to nothing and just head out. Living off the kindness of strangers is certainly possible along the road, but there are gaps and moral catches in that plan that must be considered. Living off the land is a fallacy and that's what the guy from "Into the Wild" found out.

Personally, I think you'd have more fun, be safer and far more comfortable if you car camped your way there and did some backcountry backpacking along the way. I've done that, and it was a lot of fun.

There is a huge difference between walking down the road and backpacking in the wilderness. I think what you're really after is the backpacking experience. With backpacking you are completely self contained and you're on public land where you're free to roam where you want. You can set up anywhere and you've got everything you need right there. You can experience a freedom, solitude, and peace and closeness to nature that is impossible in our normal environment, or even hoboing around.

If you're not an experienced backpacker or camper then you really need to start there. You don't need to be in great shape to backpack, but you do need to know how to use your gear and what to expect from it and yourself.

There aren't a lot of places to backpack in Iowa, but you can camp out, test your gear, and do some hiking where there is peace and solitude. I've camped and hiked at the Yellow River State Park there and that would be a good spot to get a feel for things.

You'll find a great deal of info and help here on getting started with backpacking. I think if do start with backpacking you'll learn how to find the experience you're looking for. I'd liken it to a 1000 mile short cut to find the really good spots.