I'm currently in columbus, born and raised. I'll be going to Sacramento, which is about 2,500 miles. I'm still planning out my trip, but I'll likely make the 6 hour trip to chicago first and visit some friends then head out in the morning from there, picking up I-80 which will take me all the way to my destination. Yup, that's over 2 days on the same road! Makes it virtually impossible to get lost, but a few turns or exchanges would keep me a little more alert.
I'm going to map out several different motels along my way and I always carry a few blankets in the car anyways, so just in case I get too tired I can pull off the road anywhere. I'm also going to put a few minutes on my extra Net10 phone, because it's the only phone I've used that seems to get service in very remote areas, unlike my tmobile iphone. It's just an extra precaution incase something happens.
For those that didn't already know, I drive a jaguar which I have yet to make an out of state trip without something breaking or failing. Nothing like coming back from SC and having your water pump fail in the summer time. Why do I mention the car? Well, jags aren't known for being very reliable. And I've spent the last few weeks working on fixing its most recent misfiring problems. It seems ok right now, and I have tools and extra parts with me just in case something happens on the road this time.
Longest road trip I've made is from columbus to myrtle beach and back in 2 days when I was 20yr old. But I've made frequent 500 mile trips to pocono. Wish I had an mp3 player in the car, but the 6 disc changer will have to suffice.

"Any sufficiently advanced technology is indistinguishable from magic" ~ Arthur C. Clarke