Natchez Trace Parkway.
444 miles. Bucket list item I've yet to do. Start up near Nashville and wind up in Natchez MS seems the logical way to go. I live next to it near the 100mi marker. I've met a lot of people doing that ride. The last three groups doing it backwards. But whatever!
6) Drivers who won't kill you. Most won't kill you. A few will annoy you and make you shout bad word and gesture obscenely at them.
https://natcheztracetravel.com/biking-the-trace.html
Mount Blue Sky (formerly Mt. Evans) in Colorado.