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I live in South Chicago and I’m thinking about loading my bike and heading south in December to ride in a warmer climate for a few days. Can anyone give me some insight on good road riding in Tennessee,Missouri, or Louisiana area. Thanks :)
 

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Natchez Trace or East TN. Completely different terrain, though, but they offer a good spectrum of riding.

EDIT: Oh, and Arkansas has really challening mega-rollers in the Ouachita and Ozark Forests. That's probably as warm as Missouri.
 

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East TN is only what I can answer extensively, although I've ridden several hundred miles in AR and MO.

https://www.facebook.com/knoxvelo1/

https://sites.google.com/site/scoclub/

We have lots of hills, and winter riding can present unique challenges. You huff and puff up steep climbs and then you bomb down them with lots o' wind chill. But if you're from CHI that shouldn't be a problem.

I know Knox Velo has a Winter Training Series (~55 miles each Sunday), SCO probably has something equivalent.

You can also google bike shops in town and call them. That goes for any area you're interested in riding. Forget LA, that's going to be all flat and boring, although temps won't be bad.

What kind of riding are you looking for? Do you want hills, hard rides, long distances? Any aspirations for gravel? Do you want amenities? (Also known as the coefficient of debit card).
 
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