Written By Matt Smith

Welcome to the Kentucky Bourbon Trail

Ready to sip, savor, and explore the best of Kentucky bourbon? A long weekend on the Kentucky Bourbon Trail offers the perfect blend of history, culture, and flavor. This 3-day itinerary is designed to maximize your time, with visits to world-famous distilleries, delicious dining options, and charming places to stay. Let’s get started!


Day 1: Arrival in Louisville

A glass of bourbon on the rocks with a warm amber glow, capturing the essence of a Day One experience on the Kentucky Bourbon Trail in Louisville.

Kick off your Kentucky Bourbon Trail adventure in Louisville with iconic distilleries, great dining, and unforgettable bourbon experiences.

Morning: Explore Louisville’s Bourbon History

Start your trip in Louisville, the gateway to the Bourbon Trail. Begin with a visit to the Frazier History Museum, the official starting point of the Bourbon Trail, where you can pick up your Bourbon Trail Passport. Don’t miss their bourbon-centric exhibits to learn about the history and heritage of Kentucky’s signature spirit.

  • Lunch: Harvest – Savor farm-to-table Southern cuisine with a modern twist. Try their bourbon-glazed pork chops!

Afternoon: Distillery Tour & Tasting

Tour the iconic Angel’s Envy Distillery, conveniently located in downtown Louisville. Their guided experience includes a behind-the-scenes look at how their award-winning bourbon is crafted and finishes with a tasting.

  • Dinner: Doc Crow’s Southern Smokehouse & Raw Bar – A perfect spot for bourbon cocktails and barbecue. Pair your meal with one of their expertly crafted bourbon flights.

Where to Stay in Louisville

  1. Luxury: The Brown Hotel – Famous for its historic charm and the legendary Hot Brown sandwich.
  2. Mid-Range: 21c Museum Hotel – A boutique hotel featuring contemporary art exhibits.
  3. Budget: Galt House Hotel – Affordable with unbeatable views of the Ohio River.

Day 2: Distillery Hopping in Bardstown

A bourbon cocktail with an orange garnish served in a rustic Bardstown setting, capturing the essence of Day 2 on the Kentucky Bourbon Trail.

Day 2 on the Kentucky Bourbon Trail: Bourbon Cocktails and Distillery Adventures in Bardstown

Morning: Head to Bardstown, the Bourbon Capital of the World

A short drive from Louisville brings you to Bardstown, a picturesque town filled with bourbon history. Begin with a tour of Heaven Hill Distillery, home to brands like Elijah Craig and Larceny. Their bourbon-tasting experience is a must.

  • Lunch: The Old Talbott Tavern – This historic spot offers hearty Southern dishes and a cozy atmosphere.

Afternoon: Iconic Distillery Experience

Next, visit Maker’s Mark Distillery, where you can hand-dip your own bottle in their signature red wax. The grounds are as stunning as the bourbon, making it a fantastic stop for photos.

  • Dinner: Mammy’s Kitchen & Bar – Enjoy classic Southern comfort food, from fried chicken to bourbon bread pudding.

Where to Stay in Bardstown

  1. Luxury: Bourbon Manor Bed & Breakfast – A charming, bourbon-themed B&B with exceptional hospitality.
  2. Mid-Range: Hampton Inn Bardstown – Convenient, comfortable, and just minutes from top attractions.
  3. Budget: SureStay Hotel by Best Western – Clean, affordable, and centrally located.

Day 3: Lexington’s Bourbon and Beyond

Woodford Reserve Distillery with its iconic limestone buildings surrounded by lush greenery in Lexington, featured for Day 3 of the Kentucky Bourbon Trail.

Discover Lexington’s bourbon heritage on Day 3 with a visit to Woodford Reserve, where tradition meets scenic Kentucky charm.

Morning: Scenic Drive to Lexington

On your final day, head to Lexington, where bourbon meets horse country. Start with a tour of the Woodford Reserve Distillery, one of the most picturesque stops on the trail.

  • Lunch: Wallace Station Deli & Bakery – A favorite for its fresh sandwiches and bourbon-inspired desserts.

Afternoon: Discover Town Branch

End your bourbon journey at Town Branch Distillery, known for its innovative whiskeys and ales. Their tour showcases both bourbon and craft beer, making it a unique stop.

  • Dinner: Jeff Ruby’s Steakhouse – Treat yourself to a luxurious steak dinner paired with bourbon from their extensive list.

Where to Stay in Lexington

  1. Luxury: The Campbell House – A historic hotel with modern Southern elegance.
  2. Mid-Range: Hyatt Regency Lexington – Perfect for convenience and comfort downtown.
  3. Budget: La Quinta Inn & Suites – A budget-friendly option with great amenities.

Tips for a High-Spirited Weekend

  1. Book in Advance:
    Many distilleries require reservations for tours and tastings, so book your spots ahead of time.
  2. Get the Bourbon Trail Passport:
    Pick up a passport at your first distillery or the Frazier History Museum. Collect stamps at each stop and earn rewards!
  3. Pace Yourself:
    Distilleries often offer generous pours. Share tastings or sip slowly to enjoy responsibly.
  4. Stay Hydrated:
    Bring water and snacks to keep your energy up throughout the day.
  5. Use a Driver Service:
    Stay safe and let someone else handle the driving by booking through Welcome Pickups.

FAQ: Kentucky Bourbon Trail

Q: How many distilleries are on the Bourbon Trail?
A: The official Kentucky Bourbon Trail features 18 distilleries, with additional stops on the Craft Tour.

Q: Do I need to be a bourbon expert to enjoy the trail?
A: Not at all! The trail is beginner-friendly, with plenty of guided tours to teach you about bourbon.

Q: When is the best time to visit?
A: Spring and fall are ideal for mild weather, but the trail is enjoyable year-round.

Q: Are children allowed at distilleries?
A: Some distilleries allow children on tours but may have restrictions in tasting areas. Check with individual locations.

Q: What should I wear?
A: Comfortable clothes and shoes for walking tours. Many distilleries are on scenic grounds.


Ready to Hit the Bourbon Trail?
With this 3-day itinerary, you’re all set to sip your way through Kentucky’s best bourbon distilleries, enjoy delicious meals, and find great places to stay.

Book your stay now and let the adventure begin!

Written By Matt Smith

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