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Courtesy Trail Hotel
With its modern facade, chic interior design, sexy speakeasy, and high-end surf and turf restaurant, it’s hard to believe that the building housing the Trail Hotel was once a Holiday Inn. But talk to natives of Bardstown, Kentucky, and you’ll learn that the former chain property was the place to see and be seen from its opening in 1970 through the ’90s. That happening energy is what the Trail Hotel wants to rekindle—albeit with an upscale, boutique atmosphere and an emphasis on the area’s iconic bourbon scene. After all, Bardstown is known as the Bourbon Capital of the World.
Courtesy Trail Hotel
You appreciate the centrality of bourbon to the Trail experience upon booking, when the hotel’s Bourbon Butler reaches out to assist with reserving exclusive VIP experiences, such as tailored itinerary planning, private barrel tastings, and distiller meet and greets. The property also hosts daily distillery tours to area greats such as Maker’s Mark and Heaven Hill.
The 95 rooms and suites, which form a motel-style U shape around the pool and Swim Club Bar, reinforce the imbibing theme with spirit-inspired decor, from the shades of copper reminiscent of whiskey stills to framed prints of vintage bourbon ads.
Courtesy Trail Hotel
If the thought of a hangover is daunting, fret not. The Trail Hotel offers a host of remedies, including IV therapy, an oxygen bar, a sauna, and cryotherapy. And there’s always the swanky lobby bar if a hair of the dog is more appealing.
Insider Intel
Bourbon Butler Norma Smith shares her Bardstown favorites
Vintage Gems
“I love all the museums here, but my favorite is the Oscar Getz Museum of Bourbon History. They have an incredible display of old, dusty bottles, including several brands that were lost to Prohibition.”
Kings of the Hills
“Our local distilleries, like Bardstown Bourbon Company and Jim Beam, do an amazing job hosting community events, from live music to creative cocktail nights. I especially love when these gatherings are outdoors, so you can enjoy good bourbon surrounded by the rickhouses and rolling hills.”
Urban Appeal
“The cocktail menu and bourbon selection at Liam Ash Cocktail Emporium could easily hold its own in a big city, but the staff treats you with that small-town hospitality Bardstown is known for.”
This article appears in the Fall 2025 issue of Southbound.
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