I did it out and back from Port Gibson, MS. We dry camped and resupplied at towns along the way. I would go early spring as we did it in mid June and just about died from the heat. I suppose if you stayed in hotels it would be nicer cause trying to sleep in a tent when it is about 85 degrees isn't that much fun and the skeeters are wicked anywhere there is water around. Great riding though. If you get a chance the Vicksburg National Military Park is off the Trace a ways, but is one of the neatest Military Battlefields in America. I promise you, you will never appreciate Tupelo , Mississippi more than when you arrive by bike via the Trace. I don't think I was ever more happy to see a town in my life than Tupelo. We stayed in a cheap hotel with real air conditioning and a real shower. That was thirty some years ago and I remember it like yesterday.

Total thread drift, but the Katy Trail across Missouri would be a fun one to look at too. I have not done it, but have seen parts of it.