I have never been to Kentucky and am wondering if taking a route that direction makes sense. We are wimps and only drive about 300- 400 miles a day, depending on variables like weather. We're driviing this June.

We're in no hurry and want to make this roadtrip leisurely and fun. (But no side-trips that create more driving.) I'd like to hear what towns might be attractive to stop in along the way, and recommendations for inexpensive motels to stay in.

Thank you!
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The quickest route by about an hour or so is the northern route through northern Ohio, Nebraska, etc. Since you are only driving about 300-400 mpday, the shortest route would make more sense, and that is simply straight out I70. Going through Kentucky would add about 70 miles (or more, depending on where in KY)to the short route and is far out of the way of the northern route. If you go to Kentucky, you may enjoy Mammoth Cave National Park. The longer tours are exceptional.
If you go out I70, you may want to visit the Airforce Museum near Wright Patterson AFB in Dayton. It is a bit out of your way, but IMO, worth it if you are interested in a great display of aircraft from WWI to the present and more. St. Louis has its arch that you may want to visit. We enjoyed driving through Kansas just for the flatness and unending fields. We were able to see weather patterns that were hours away.
If you take the northern route and like amusement parks, try Cedar Point west of Cleveland. Although justly famous for is roller coasters, they have nice entertainment as well.

I try to avoid I-70 across Missouri. It is a miserable road.

Keith

Keith, I completely agree with you - too much traffic, not enough lanes and poor road maintenance. I think it is scary.