Just got back from a long vacation, and almost all of the return trip, we drove the freeways that largely parallel R66 from Gallup back to Chicago.
Back in the 00's, we took Rt66 from just outside of Chicago to Tulsa, and had a fun time. From an interesting drive standpoint, probably Illinois is the best, as you do go through a lot of smaller towns and there are still some interesting small Motels on the way. So we thought it would be fun to take our classic car on the road all the way to the coast.
Until we did what we just did. The parts we did see, the road is hardly perfect, so we know that the road quality out west isn't all that great. Add that to the endless miles and miles of nothing, I can't really think it would be either fun or interesting to take Rt66 from just outside OK City all the way until past Gallup NM. Out west, there's just nothing there. Especially from OKC to about mid New Mexico. Barely interesting geography and almost no towns to stop in- just empty road. For two of of the stops, we did Rt66 hotels. Meh on one- Elk City OK has a handful of what seems to be original Motels, but they are quite a bit by themselves, and you still have to drive to get food- not fun after a long day of driving. The one in Springfield MO was better, as it's older and has some cool theme rooms.
But be clear, the motels available do leave some to be desired in terms of comfort relative to big chain hotels that are at least consistent.
Maybe I'm too old to think that driving in an uncomfortable way is fun. Then again, I never really thought it was that fun. It's interesting to watch Roadkill and see them struggle driving- but have you noticed they are always in big chain hotels on their drives?
Anyway, what seemed to be an interesting thing to do during retirement has been officially taken off our "to do" list. Sometimes just taking the freeway is the better option- smoother and faster.