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Pride Journey: The Kentucky Bourbon Trail

On a snowy weekend in January, a group of friends and I decided to rent a Vrbo in the heart of Bourbon country. Of the five of us, I was the only one who had the opportunity to visit this part of Kentucky, so I was excited to experience this weekend with my partner and some close friends.

Our Vrbo was located on a remote road in Lawrenceburg, less than 10 minutes from town and some popular local attractions. The two-story cabin featured two bedrooms, two baths, and a lovely wood interior, giving it a log cabin feel. The cozy living room was perfect for playing games by the fire and sharing some wine – and whiskey – with friends.

Nestled in the heart of Kentucky, the Bourbon Trail is a journey that beckons both whiskey connoisseurs and casual enthusiasts alike. This iconic trail winds its way through the picturesque Bluegrass State, offering a unique and immersive experience into the world of bourbon, America's native spirit. From the rolling hills of horse country to the historic distilleries that dot the landscape, the Kentucky Bourbon Trail weaves together the rich tapestry of bourbon's heritage.

To truly appreciate the Kentucky Bourbon Trail, one must understand the deep-rooted history of bourbon itself. Bourbon, by definition, is a type of whiskey that must be made in the United States, with at least 51% corn in the mash bill, distilled to no more than 160 proof, and aged in new charred oak barrels. The origins of bourbon can be traced back to the late 18th century, with Kentucky gaining prominence for its fertile soil and limestone-rich water—ideal conditions for producing exceptional bourbon.

Our first stop was Four Roses Bourbon, a renowned bourbon producer with a rich history dating back to 1888. Situated in Lawrenceburg, Kentucky, Four Roses has become synonymous with exceptional craftsmanship and distinct flavor profiles in the world of bourbon. The distillery is known for its unique approach of using two separate mash bills and five proprietary yeast strains, allowing for the creation of ten distinct bourbon recipes. Each recipe produces bourbons with varying characteristics, from delicate and fruity to robust and spicy. Four Roses has gained widespread acclaim for its commitment to quality and tradition, earning numerous awards for its premium bourbons. Visitors to the distillery can explore the picturesque grounds, witness the meticulous bourbon-making process, and enjoy tastings of their signature expressions, making it a must-visit destination for bourbon enthusiasts.

Lawrenceburg is also home to the T.B.Ripy House, the historic home of prominent distiller and whiskey baron, Thomas B. Ripy. We received a private tour of the 11,000-square-foot Queen Anne-style mansion by its current owner, a descendant of Thomas Ripy. The home, built in 1888, went through a few owners over the years and requires some repairs, but the main level is a beacon of history and transports guests back to the Gilded Age period. It is a true treasure of Lawrenceburg.

We then headed to Woodford Reserve, nestled amid the serene horse farms of Woodford County. Woodford Reserve Distillery stands as a distinguished gem in the heart of Kentucky's bourbon country. Nestled amid the serene Bluegrass region in Versailles, Woodford Reserve is celebrated for its commitment to producing small-batch, handcrafted bourbon of the highest caliber. Established on the historic grounds of the Old Oscar Pepper Distillery, dating back to 1812, Woodford Reserve meticulously follows time-honored techniques in its artisanal bourbon-making process. The distillery is renowned for its copper pot stills, unique triple-distillation method, and maturation in charred white oak barrels. The result is a smooth and complex bourbon with notes of dried fruit, vanilla, and a touch of spice. Visitors to Woodford Reserve can partake in guided tours or indulge in tastings of this esteemed bourbon, making it a quintessential destination for aficionados and curious spirits enthusiasts alike.

If you are hungry, swing by the legendary Kentucky Castle, an icon in Versailles. The castle is truly majestic inside and out and contains numerous guest rooms, a restaurant, a spa, stables, and luxurious glamping options. The brunch at Castle Farm left a lot to be desired. The food was good at best. The eggs were overcooked. The brisket was fatty, and the service was very slow. I hate to say you are paying for the location but in this case, it seemed that way. I would give them another try though. Everyone has a bad day.

The Kentucky Bourbon Trail is more than just a collection of distilleries; it's a celebration of tradition, craftsmanship, and the art of bourbon-making. As visitors traverse the scenic landscapes and delve into the history of each distillery, they gain a deeper appreciation for the time-honored techniques that define Kentucky bourbon.

For bourbon enthusiasts and those eager to explore the roots of America's native spirit, the Kentucky Bourbon Trail is a captivating journey through time and taste. Each distillery on the trail offers a unique perspective, contributing to the rich narrative that makes bourbon an integral part of American culture. Whether you're sipping a carefully crafted small batch or learning the nuances of the distillation process, the Kentucky Bourbon Trail promises an unforgettable experience for all who embark on its spirited path.

There aren’t a ton of hotels in the region, so booking a Vrbo is the way to go. Vrbo is the first major vacation rental platform with a rewards program, where travelers can earn OneKeyCash rewards from the booking. Vrbo vacations are one of the quickest ways to earn OneKeyCash and One Key status.

To book your Bourbon Trail holiday, please visit


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