Kentucky Bourbon Trail Trip Planner
If You Can’t Make It to Scotland, This Is the Place to Visit
I’m gearing up for my upcoming trip along Kentucky’s legendary Bourbon Trail, and I wanted to share our trip plans with you. Use this trip plan as your own guide! Customize it to fit your schedule, add your favorite stops, and enjoy a Kentucky adventure as rich and rewarding as the bourbon itself. Make your next visit to Kentucky Top Shelf worthy.
This itinerary offers a perfect blend of scenic landscapes, rich history, and world-class bourbon. Whether you’re into the stories behind each brand, the artistry of bourbon-making, or just want a scenic road trip with great drinks, Kentucky’s Bourbon Trail has it all.
“I’d rather be someone’s shot of Bourbon than everyone’s cup of tea”
Day 1: Start at Maker’s Mark — The Art of Craftsmanship
Begin your journey at Maker’s Mark in Loretto, where you’ll see the meticulous process of hand-dipping bottles in red wax. It’s a historic and charming distillery that offers great photo opportunities and a behind-the-scenes look at artisanal bourbon craftsmanship. Don’t miss the chance to learn about Bill Samuels’ recipes and the tradition behind every bottle.
Capture photos of the iconic wax seals and maybe even try your hand at dipping a bottle. Rumor is it’s trickier than it looks!
Day 1: Visit James B. Beam — A Legacy of Innovation
Next, let’s explore the James B. Beam Distilling Company in Clermont. With roots dating back to the 1800s, it’s a cornerstone of Kentucky bourbon history. Tour the historic warehouses, learn about the Beam family’s innovations, and sample their legendary bourbons.
Be sure you check out the family portrait wall and the historic architecture as they make great photo backdrops. Toast your visit with a glass of their finest.
Day 1: Stroll Through Bardstown — The Heart of Bourbon
Spend some time in Bardstown, often called the “Bourbon Capital of the World.” Walk the charming town square, visit local shops, and chat with passionate bourbon enthusiasts.
Day 1: Time to Wind Down
After exploring, enjoy dinner at either The Rick House or Old Talbot Tavern—both offer fantastic local flavors and a cozy atmosphere. Vintage signs, cozy storefronts, and friendly locals make for memorable shots.
Time to check into The Trail Hotel, your comfortable base for the night. They afford a perfect blend of nostalgic charm and contemporary luxury for those seeking memorable moments, great company, and exceptional bourbon experiences.
“BOUR-BON / bʊər bən noun
Magic brown water for fun people.”
Day 2: Discover Elegance at Four Roses
A visit to Four Roses in Lawrenceburg offers opportunities to learn about their unique yeast strains and blending techniques that produce aromatic, floral bourbons. Tour the distillery, observe their production process, and enjoy tastings of their refined spirits.
Capture the distillery’s beautiful architecture and take a moment to smell the aroma of their signature bourbon, almost as good as stopping to smell the roses.
Day 2: Experience Small-Batch Perfection at Woodford Reserve
Drive over to Versailles to tour Woodford Reserve, known for its small-batch approach. See copper stills in action, learn about their meticulous process, and indulge in tastings of their premium bourbon.
Take a scenic photo of the distillery grounds and enjoy a tasting with a caption like “Small batch, big flavor.”
Day 2: Step Back in Time at Buffalo Trace
Make the short trip to Frankfort for a visit to Buffalo Trace—one of the oldest distilleries in America, dating back to 1773. Tour historic warehouses, hear legendary stories, and taste famous bourbons like Eagle Rare and Blanton’s.
Fun fact: if you’re into ghost stories, you might even catch a spooky tale or two from the staff!
Day 2: Relax and Reflect Over a Cocktail
Visit the Lexington Distillery District for shopping, dining, and a visit to James E. Pepper Distillery, originally opened in 1879. Grab dinner at the Barrel House, known for its delicious southern cuisine and bourbon-inspired cocktails before heading to your lodging. It’s the perfect spot to relax and fuel up for the next days adventures. Other dining options to choose include Jeff Ruby’s Steakhouse or Cole 735 Main—both offer excellent steaks, refined atmospheres, and great drinks.
Retire to the Campbell House for your overnight lodging. This hotel speaks to the history of horse racing in Kentucky and is a curio collection hotel in the Hilton umbrella. Dining options are available including Rackhouse Tavern if you didn’t grab a bite in the Distillery District. Cap off your evening with drinks at The Bourbon Bar offering a selection of 11 flights of bourbon just in case you need a night cap.
Day 3: See Barrel-Making Magic at Kentucky Cooperage
No bourbon is complete without its barrels, and at Kentucky Cooperage, you’ll watch master coopers craft oak barrels that give bourbon its signature flavor. It’s a fascinating look at the craftsmanship behind the spirit.
Photo ops include close-ups of the coopers at work and freshly made barrels.
Day 3: Celebrate at Heaven Hill — A Testament to Resilience
Your trip concludes at Heaven Hill, which survived Prohibition and a fire to keep their bourbon tradition alive. Tour the visitor center, taste their finest bourbons, and toast to Kentucky’s enduring spirit.
Raise a glass in a celebratory toast and capture a memorable selfie to end your bourbon adventure.
Day 3: Return Home
As you head home, you'll carry with you lasting memories of a trip filled with rich history, expert craftsmanship, and some of the best bourbon in the world. I hope you leave with a few bottles that become both priceless keepsakes and delicious reminders of your experience.
And if you’re dreaming of Scotch in Scotland, but can’t quite get there, Kentucky’s bourbon trail is the next best thing.
