Country music stars such as Loretta Lynn, Dwight Yoakam, Ricky Skaggs, the Judds, Billy Ray Cyrus, Patty Loveless and several others have lived along this 130-mile stretch of U.S. 23, which runs from Ashland to Jenkins, and you’ll see monuments and other tributes to them along the way. Be on the lookout for local music festivals (they’re held almost constantly).

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Where to Eat?

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