I'm a teacher and live in Iowa. I plan on doing two loaded tours this summer, one in the beginning and one at the end of summer. I've done quite a bit of riding, but this will be my first "loaded tour".
The questions that I have is that I need some advice on firming up my route and being confident in my decision. I know the destination I want to arrive at and feel like I have a good idea which route I want to take, but I want to get a few questions answered. First, I ride feel like I ride quite a bit on the roads around here and am pretty confident but what do I need to remember as I spend a week and a half on county and state highways? Am I crazy for thinking it is OK for me to just get on the highway and head to my destination? What are your experiences with this?
Also, I've got a pretty good idea of the supplies I'll be needing but can anyone think of some things that you've gotten a few days into a ride and said "why did I not think of that".
You are not crazy for wanting to improvise. If you have good maps and a gps, keep your daily goal reasonable (say under 40 miles) to allow for the unknown and know when to check in at a motel to recoup, then it is fine. It's a matter of doing enough prior research as to what is on-route for services and food, and carrying the right spares. Hub-and-spoke type touring is often done this way.
Some first-time riders take a lot of stuff, but not what they really need. Consider what can go wrong when you're on a tour and prepare for those things.
For a summer tour, I can expect flat tires, minor mechanical problems, cold rain, cool nights and hot days, so I'll prepare for them. The rain might not come, the days might be warm and the nights pleasant, but in case I hit rough weather, I'm ready. And I may go the entire trip without a flat, but that's not guaranteed. In case of an emergency, I'll carry spare tubes and tire patch supplies, tools I need to rig the bike in case of an emergency, rain gear, cool weather gear and clothing for hot days. If I've got that covered, I'm fine. My camping gear is as minimal as I dare to take, again covering everything that can realistically happen on a trip.
If the trip is in Iowa or nearby areas, you don't need much in the way of food. Towns there are reasonably close together and you can stop before the end of the day to pick up what you need for the evening meal. If it's a trip in hot weather, you could possibly leave the camp stove, fuel and cooking ware behind and go with foods that require no cooking. That's getting quite minimal and there is something to be said for a good meal at the end of a day of riding. If you were in a sparsely populated area, you would need to take more food with you and you might need to pack extra water. Where you're going, you won't ever be far from those things.
Definitely assess what you really "need" (subjective, I know). My first tour was a small group trip x-country. One woman brought a blow dryer and, get this, a Sony Watchman TV. She mailed them and other stuff home at the beginning of the 3rd. day. A few others also mailed stuff home that day. They were happy when we hit the mountains a few days later.