Jailer's Inn is a romantic B&B today for any bourbon-lover, but it's got an odd history—it was named the quirkiest lodging in America by TripAdvisor. The bed and breakfast is located on the property of the old Nelson County Jail, which incarcerated prisoners from 1797 to 1987.
The private, elegant rooms are decorated with antiques and heirlooms, and they vary in type; some feature four-poster beds, vintage books, and hand-hewn timbers, while the Jail Cell resembles just that, complete with an Elvis poster circa "Jailhouse Rock."
Each morning, the friendly innkeeper sets out a full, hot breakfast.
You can take a free tour of the historic back jail, which has remained unchanged since it was built in 1874.
Bardstown, Kentucky: Bourbon Capitol of the World and Kentucky History
Set down in between Louisville and Lexington, Bardstown was named The Most Beautiful Small Town in America by USA Today in 2012. It's also one of Kentucky's oldest cities, established in 1788. The downtown area is chock-full of venerable buildings and listed on the National Register of Historic Places. When checking out the historic structures, make sure to visit Wickland, a circa-1825 mansion that's been home to three Kentucky governors and is open for tours. Also worth a stop: My Old Kentucky Home, a state park spot that houses the mansion that inspired Kentucky's state song "My Old Kentucky Home."
Bardstown is nicknamed the "Bourbon Capital of the World"—it's the home base of Jim Beam, Heaven Hill, and Maker's Mark distilleries, and also plays host to the annual summertime Kentucky Bourbon festival. If you're a bourbon lover, be sure to tour the distilleries and sample tastes of the amber liquid, then head over to the Oscar Getz Museum of Whiskey to learn about the history of whiskey distillation and see rare artifacts from pre-Colonial days.
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