We try to get a general idea from looking at maps, but then we talk with the local people to get their perspective. I think you'll find people are more than happy to help you figure out a route!

Since we are out for an extended period of time, we don't sweat the small stuff - anything less than 300 miles isn't that big of a deal for us. If we find ourselves on an ucky, boring road for a few hundred miles, we just tune it out and pedal. If you are only riding for a couple hundred miles, you wouldn't want the whole time to be in ucky scenery, so will have to pick your route more carefully.