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You might have better luck in reverse, live in Charlottesville and travel to Lexington for the occasional show. They are about an hour apart. Charlottesville has a much better live music scene than I would suspect Lexington would. But I'm not sure. While Lexington is a totally cool little town, it's just that, extremely small. The biggest city close by is Roanoke 45 mins down the road. In C-ville you have the option of going to Richmond an hour away or DC 2 hrs away. If you want a combination of the two towns I strongly suggest where I live, Staunton. Bigger than Lexington with the same charm and character downtown but smaller than C-ville. It's also dead center in between them, Lexington 30 mins south and C-ville 30 mins east. There are also several restaurants, not chains, in downtown Staunton that have live music. Several I believe actually have jazz on certain nights. And in the summer at the park they have free live jazz concerts. Good luck with your decision!
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