Kentucky Bourbon Trail Uncorked: A 4-Day Itinerary

Tips for a Smooth Bourbon Trail Experience

• Drink Water Frequently – Carry a water bottle, pace yourself, and don't skip meals.

• Ask Each Distillery About Exclusive Bottles – Many offer bottles only available at the gift shop.

• Look Online Before You Buy Bottles – Before purchasing bottles, look them up online. Some limited releases can be found cheaper in stores or online due to distillery markups.

• Check Local Delivery Apps for Bourbon Prices – Before heading to a distillery or liquor store, browse apps like DoorDash to compare prices at nearby retailers. I recently did this and ended up visiting three different stores in one day, spotting no less than 50 bottles of Blanton’s — all under $85. It’s a great way to avoid overpaying and uncover local gems.

• Plan Lunch Strategically – Most distilleries don’t serve food; always plan meals ahead to avoid drinking on an empty stomach.

• Book Tours in Advance – Many top-tier spots like Willett, Woodford, and Buffalo Trace sell out days or weeks ahead.

• Bring Cash – Handy for small distilleries that may not accept cards and for tipping tour guides or bartenders.

• Use a Designated Driver or Tour Company – Essential for full-day outings to ensure safety and stress-free travel.

• Even small pours add up. Most distillery tastings include 3–5 samples, and it’s perfectly fine to skip one or just take a sip. Don’t feel obligated to finish every pour.

• Distilleries typically open around 9–10 a.m. and close by 4–5 p.m. Starting early gives you time to visit multiple spots and leaves room for a relaxing dinner.

    

Day 1: Louisville Legends & Flavorful First Impressions​

Morning

Start your day in Downtown Louisville, the perfect jumping-off point for urban bourbon.

 

Breakfast at Wild Eggs: A hearty Louisville favorite offering creative brunch fare and strong coffee.

 

Barrels & Billets Bourbon Experience: Located next to the Louisville Slugger Museum, this interactive experience walks you through a short tasting and a personalized test (10–20 questions) to match your flavor profile. You'll custom-blend a bottle based on your results — a fun and modern twist on traditional bourbon tasting.

     

LUNCH

Walk over to Feast BBQ or Royals Hot Chicken for some laid-back Louisville classics.

 

The Table: A pay-what-you-can restaurant in the Portland neighborhood serving delicious, locally sourced food with a mission.

   

AFTERNOON

Louisville Slugger Museum: Since you're next door, step into the world of baseball history and see how the iconic bats are made.

 

Stay local with walking-distance distilleries:

Angel’s Envy – A beautifully designed distillery with a focus on port barrel finishes. Book the Signature Tour and focus on how the port wine barrels impact flavor. A standout in finish techniques.

 

Old Forester – The only bourbon continuously sold before, during, and after Prohibition. Don’t miss the cooperage demo on-site. Cooperage tour is a must—it’s hands-on and visually dramatic. You’ve got the only on-site barrel-making demo here.

 

Peerless Distilling Co. – One of the most underrated spots in the city, known for bold, high-proof pours.  Skip a full tour here and just do the tasting bar. Their high-proof lineup is worth savoring without a repeat walkthrough.

 

Evan Williams Bourbon Experience - An immersive journey through the history of Kentucky’s bourbon heritage, featuring interactive exhibits, tastings, and a behind-the-scenes look at the distilling process.  Choose the "Speakeasy Experience" or "Ideal Bartender Experience" for a theatrical twist in a Prohibition-style setting.

   

DINNER & DRINKS​

Dinner: Jeff Ruby’s Louisville – High-end steaks, plush decor, and an excellent bourbon list. It's an ideal first-night splurge.

 

Nightcap: Head to Hell or High Water – an intimate speakeasy tucked away below Whiskey Row.

     

Day 2: Bardstown, the Bourbon Capital of the World​

Morning

Breakfast: Grab coffee and breakfast at Please & Thank You in NuLu — great biscuits, killer chocolate chip cookies.

 

Morning Drive: Depart early for Bardstown, Known as the Bourbon Capital of the World (~1 hr from Louisville).

 

Distilleries:

Heaven Hill Bourbon Experience – Great interactive exhibits and rare tasting flights. Book the "You Do Bourbon" experience – you get to taste, bottle your own bourbon, and customize the label.

 

Willett Distillery – Quirky, charming, and home to cult-favorite bourbons like Noah’s Mill. Willett is quirky and cool. Their family-led tours feel intimate and include rare pours not widely distributed.

 

Bardstown Bourbon Company – A modern, open-concept distillery with a killer cocktail bar and stylish restaurant. Instead of a tour, try their Rickhouse Barrel Thieving Experience or Bourbon Cocktail Class at their slick on-site bar.

   

LUNCH​

The Old Talbott Tavern: Operating since the 1700s, this historic site serves Southern staples in a rustic, timeworn setting. A true Kentucky classic.

    

AFTERNOON

Lux Row Distillers – Home of Rebel and Ezra Brooks, great for barrel strength lovers.

 

Barton 1792 - A well-known Kentucky bourbon distillery, established in 1879 and known for its 1792 Small Batch Bourbon, a "high rye" recipe with notes of caramel, vanilla, and spice.

     

DINNER​

Try Harvest in NuLu for a farm-to-table experience that pairs well with bourbon-forward cocktails.

   

Day 3: Woodford Reserve & James B. Beam​

Morning​

Breakfast on the road: Pick up a light breakfast at Quills Coffee.

 

Drive to Woodford Reserve (~1 hr 15 min) One of the most “boujee” tours, in my opinion and it is super cool. It’s picturesque, with copper pot stills and rolling bluegrass horse country views. Try their Double Oaked. Choose the Corn to Cork experience for a complete look at the process with barrel tastings. Great photography, too.

 

Wild Turkey – Visit the rickhouses and enjoy panoramic river views. Try the Russell’s Reserve line. Skip the full tour here; instead, enjoy a tasting flight and spend time soaking up the views from the visitor center.

     

LUNCH​

The Kitchen Table Located at the Jim Beam American Stillhouse in Clermont. This spot offers Southern hospitality, modern Kentucky flavors, and a view of the rackhouses while you eat. Try the pork chop or fried chicken.

    

Afternoon​

Jim Beam Distillery Big, bold, and immersive. The tour includes tastings of core and small-batch brands. Take the time to visit their gift shop — Beam often has location-specific bottles or unique blends. Consider the Distillers’ Collection Tasting or Behind the Beam, which dives deeper than the general tour.

 

Four Roses (Lawrenceburg) – Spanish-style architecture and sweet, delicate bourbon. Do the Heritage Tour if you want a quieter, architecturally beautiful stop with sweet, floral bourbon notes.

 

Bluegrass Distillers Small batch and experimental, for those who like the road less traveled. Tasting only is best here. Chat with staff about mash bills—they're passionate about rye-forward styles.

    

DINNER​

Watch Hill Proper Located in Norton Commons, this is the world’s most extensive American whiskey bar. The food is elevated and delicious, and their staff is super knowledgeable if you want to try something rare or different. Perfect finale. Consider a curated flight or guided vinatge tasting.

   

Day 4: Lexington, Frankfort, & Beyond​

Morning​

Wiltshire Pantry Start your day on a cozy note. If you're near NuLu, grab a warm croissant sandwich and a locally roasted pour-over at Wiltshire Pantry Bakery & Café—the kind of quiet, charming spot that locals treasure.

 

Michter’s Fort Nelson Distillery (Louisville) Kick off your final day with a deep dive into history and innovation at Michter’s. Their tour is tight, informative, and beautifully staged inside a restored historic building. What really sets Michter’s apart is the attention to detail—from their small-batch process to the pristine presentation in the tasting room. Don't miss the chance to sample one of their rare or distillery-exclusive barrel picks—you’ll understand why their reputation stretches well beyond Kentucky. Taste of Fort Nelson is a great option—focuses on a guided tasting and their history, especially the Fort Nelson pot still.

 

Maker's Mark (Loretto) When you're visiting the Maker's Mark distillery on the Bourbon Trail, one of the most fun experiences is dipping your own bottle in wax. However, I’d recommend going for a smaller bottle, especially since it’s more affordable and easier to handle. Dipping a larger bottle can be tricky, and chances are you won’t finish it all. A smaller bottle not only saves you money but also makes for a great souvenir that's easy to transport. Plus, the dipping experience is just as special, no matter the size, so you’ll get to enjoy the fun of personalizing your bottle without the commitment of a bigger one!"

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Kentucky Cooperage (Lebanon) Take a rare behind-the-scenes look at one of bourbon’s most essential (yet often overlooked) elements: the barrel. At Kentucky Cooperage, you can witness expert coopers crafting white oak barrels by hand, flames roaring as they char the wood to perfection. This stop adds context and craftsmanship to everything you’ve tasted—because without the barrel, there’s no bourbon. Call ahead to time your visit with the production floor in action. This is unique and adds variety to the trail. Confirm timing with Independent Stave Company.

    

LUNCH​

The Stave (Frankfort) Nestled along Glenn’s Creek between distillery stops, The Stave is a hidden gem with big flavor. The menu is Southern-inspired but elevated, with locally sourced ingredients and an impressive selection of rare bourbons behind the bar. Try the bourbon-glazed pork belly or hot brown fries, and enjoy the rustic-modern patio if weather allows. This is the kind of place where you’ll want to linger a bit longer—thankfully, it’s right on your path to Buffalo Trace.

    

AFTERNOON​

Buffalo Trace Distillery (Frankfort) One of the most iconic names in bourbon, Buffalo Trace blends prestige with approachability. The tours are well-paced, informative, and—best of all—free (though reservations are a must). From Eagle Rare to Blanton’s, you’ll get a sense of legacy in every brick and barrel rack. The tasting is generous and often includes distillery-only options you won’t find elsewhere. Make sure to explore the gift shop—it’s one of the best on the trail. The Hard Hat Tour (if available) shows more behind-the-scenes. Otherwise, their standard tour and tasting is iconic and free. If you're looking for those hard to get allocated bottles, be sure to keep an eye on the daily product availablity and the daily odds to get an idea of what might be offered.

 

Bulleit Frontier Whiskey Experience (Shelbyville) Finish the day with a modern take on bourbon at Bulleit. This visually striking facility is as bold as the whiskey itself, with a contemporary visitor center, hands-on exhibits, and a well-curated tasting bar. It’s a great photo stop, and their innovative approach (think cocktail classes and sustainability showcases) makes for a dynamic final impression on your bourbon journey. Book the Bulleit Frontier Whiskey Experience if it’s your first time, or the cocktail-making class for something different

    

DINNER​

OBC Kitchen (Lexington) End your day in Lexington with dinner at OBC Kitchen, a warm and refined bourbon-centric spot beloved by locals and bourbon aficionados alike. Their selection of rare and vintage pours is one of the best in the state, and the food more than holds its own. Think duck fat fries, smoked meats, and indulgent desserts—perfectly paired with a pour of something special. Toast your last night on the trail in style. Ask the staff for a “bottle challenge”—they often have rare single-barrel picks not on the menu.

    

Optional Add-On

Jack Daniel’s (Lynchburg, TN): If you’re up for a longer drive (about 3.5 hours one-way), it’s possible to tack this onto an extended trip.