Which USA towns to experience rural South?

I’m going on a rock festival to Louisiana in October. From there I’d like to visit maybe 3 places and be gone by new year. What I’m looking for are dreamy rural towns ~50k in size that haven’t changed much and will allow me to briefly experience how it is living in the South/SE USA. Another thing is since I’m coming in Fall, what will the weather be? Where I’m coming from, November is all rain, clouds, winds and 10 degrees (so the crappiest weather possible). Are my filters yielding any results? Thanks!

Natchez, MS - one of the wealthiest cities in the US during slavery, big architectural legacy
Oxford, MS - great food, stay for the insane parties for the college football team in the fall
Clarksdale/Greenwood, MS - home of the blues and juke joints, also the ‘crossroads’ where Robert Johnson sold his soul to the devil for guitar skillz
Larger: Charleston, SC; Savannah, GA; Memphis, TN: Charleston for the food and yuppie rehabilitation, Memphis for the blues and the food; Savannah for the stately mansions and Spanish moss


I’m really digging Nathan’s Mississippi suggestions. I’m from Georgia, so I’ll throw in my thoughts. Rome, Georgia gets you in the Appalachian foothills and you could pop up into Chattanooga, Tennessee. Savannah, GA is great suggestion. If you get down to that area, I would tour around the Golden Islands…perhaps St. Simons and Sapelo Island. Sapelo is know for the Gullah/Geechee culture. I’m wanting to check out Fair Hope, Alabama, myself, here soon.

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Mississippi will have the best, old architecture. Everywhere else got destroyed in the war of northern aggression :wink:

+1 for Oxford, MS in the Fall. Great parties, fun times, football and beautiful women.

There are some old, Spanish mansions built by the Conquistadors still scattered around the Mississippi countryside. They’re a trip to see.

New Orleans is fantastic but not sleepy at all.

In the Fall, the weather can be nice – crisp, cool air but with sunshine. Could also be tornados. Tough to say.

Memphis is fun, but crime and violence is a very big and very real problem. Some hipster neighborhoods are fine like Cooper Young and Mid Town, but caveat emptor.

Also, Gatlinburg, TN is beautiful in the Fall – leaves changing, mountain scenery, black bears and pancakes. Will be a bit touristy, but there’s a reason everyone wants to visit it.