Jenny Wiley State Resort Park — Prestonsburg, Kentucky

Jenny Wiley State Resort Park is a full-service state resort located about 11 miles south of Van Lear in Prestonsburg, Kentucky, along the U.S. 23 Country Music Highway. The park features 49 lodge rooms, 8 cottages, 121 campsites, hiking trails, boating on Dewey Lake, and — notably for music fans — a seasonal amphitheater that hosts Broadway-style shows and musical performances.

Named for Virginia “Jenny” Wiley, an 18th-century frontier woman captured by a Shawnee and Cherokee war party, the park sits in the heart of the eastern Kentucky region that produced Chris Stapleton (from nearby Staffordsville), Ricky Skaggs, Keith Whitley, and Patty Loveless. The amphitheater and surrounding venues make Prestonsburg a natural stop for visitors tracing the Country Music Highway.