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Bourbon Trail TripDay 1: Lexington Arrival & The Manchester Experience

Planning this trip took more time than I care to admit, but it was worth it. The biggest challenge? Narrowing down which distilleries to visit — especially when you don’t want to do a full tour at each one. I leaned heavily on recommendations, reviews, and personal must-visits, then used Google Maps to chart out an efficient route. That, combined with Hotels.com, helped me put together a solid itinerary.

Wednesday, May 7 – The Road to Lexington

We hit the road Wednesday right after visiting the Atlanta United Training Facility and drove straight up to Lexington. After about six hours, we pulled into The Manchester Hotel around 7 PM — and it did not disappoint.

First Stop: Lost Palm Rooftop

Once checked in, we headed up to Lost Palm, the hotel’s rooftop bar. It’s got a 1960s tropical Florida vibe — pineapple-scented air, tiki drinks, and quirky bites like gator nuggets and short rib sliders. The views were incredible, and the energy was spot-on for a chill first night.

That said, the cocktails and food weren’t anything to rave about. But honestly, we were just happy to relax, take in the atmosphere, and ease into the trip.

Downstairs Dinner: The Granddam

After drinks and tapas, we made our way down to The Granddam, the Manchester’s main dining hall. Think upscale Bluegrass-inspired dishes, table-side juleps, and old Kentucky charm. The place had style, and the whole vibe gave off a cool nod to Southern tradition with a modern twist.

Final Thoughts on Day 1

The Manchester set a high bar — the design, the comfort, even small touches like Le Labo bath products in the room — it all made for a great kickoff. We didn’t venture out into Lexington that night; the hotel gave us everything we needed.

Bourbon Trail Trip – Day 2: Distillery Deep Dives & Downtown Louisville

Thursday, May 8th was the beginning of the trip — a day packed with bourbon history, immersive storytelling, and walking through the living, breathing legacy of Kentucky whiskey. We left Lexington in the morning and made our way to Versailles for our first scheduled tour.

First Stop: Woodford Reserve – Spectacle for the Senses Tour

Woodford’s campus is simply stunning. Tucked into the hills of central Kentucky, the distillery grounds feel like a step back in time. Jeremy, our guide, was the perfect mix of entertaining and informative. Some highlights:

Historic Status: One of only three National Historic Landmark distilleries (the others being Buffalo Trace and Maker’s Mark).
1812 Origins: Whiskey’s been made on this land since Elijah Pepper and his wife started producing it in the early 1800s.
Triple Distillation: Woodford is the only bourbon distillery in the U.S. to triple-distill using traditional copper pot stills.
Banana Bread Aromas: During fermentation, the yeast strain used gives off strong banana bread smells — and yes, we actually tasted hints of it in the final product.
Barrel Science: 80% of the flavor comes from the oak barrel. Woodford toasts their barrels before charring them — a technique borrowed from wine making to draw out richer caramel, chocolate, and vanilla notes.

Their guided tasting was incredible — from the flagship Bourbon to their Double Oak (butterscotch city) and straight malt whiskey (which smelled like Honey Nut Cheerios). The tour ended in a historic limestone warehouse that dates back to the 1800s. The air was thick with the scent of aging whiskey and history. We each left with a limited edition Kentucky Derby bottle.

Checking In: The Grady Hotel – Louisville

After Woodford, we drove to Louisville to check in at The Grady Hotel. It’s located right downtown and oozes luxury with a touch of old-world elegance. Walking distance to everything, and the rooms were top-notch.

1PM Tour: Old Forester Distillery – Whiskey Row Legacy

Our next stop was a short walk down the street to Old Forester, another Brown-Forman brand. This tour leaned more into the industrial and historical evolution of bourbon:

Founded in 1870, Old Forester was the first to sell bourbon in sealed glass bottles for quality and safety.
It survived Prohibition as one of only six companies with a medicinal whiskey license.
The brand played a major role in cleaning up bourbon’s reputation when distillers were still using additives like prune juice, tobacco spit, and worse (seriously).
Their distillery is home to Big Penny, a 44-foot copper still built by Vendome Copper & Brass Works right down the road.

The tasting included their Whiskey Row Series, with the 1910 “Old Fine Whiskey” — a double-barrel release — standing out for its syrupy, smoky finish. The tour and facility were modern and slick but full of heritage.

Next Up: Evan Williams – The Ideal Bartender Experience

Directly across the street, we stepped into a time capsule — the 1930s-style immersive bar at Evan Williams. Everything about this was theater. Phones away, lights low, and “Tom Bullock,” our Prohibition-era bartender, stayed perfectly in character:

We tasted their 1783 small batch, Bottled-in-Bond, and 12-year Red Label, all while learning how to chew our whiskey and identify flavor profiles.
Learned about the history of fake whiskey during Prohibition — kerosene, molasses, and even tobacco spit were used to mimic aging.
Fun fact: Tom Bullock (the real one) was the first Black American bartender to publish a cocktail book, The Ideal Bartender in 1917.

This was one of the most entertaining (and surprisingly educational) parts of the entire trip.

Final Stop: Whispers on Whiskey Row – Ghosts, Crimes & Murder Tour

As the sun set, we joined a 1.5-hour walking tour of downtown Louisville’s dark past. This was one part ghost stories, one part history lesson — tales of Bloody Monday riots, haunted hotels, bootleggers, and mob hits.

It added a gritty layer to the polished bourbon world we’d spent all day enjoying — a perfect contrast.

Side Notes:

Lunch was a quick pit stop at McDonald’s.
We had some cocktails at the Seelbach Hotel bar, where we learned The Great Gatsby was partially inspired. Fitzgerald drank there, and Al Capone had tunnels underneath.

Bourbon Trail Trip – Day 3: Heaven Hill, Willett, Beam & Ghosts of Old Louisville

Friday, May 9th was one of those days that somehow manages to be spontaneous and unforgettable — the kind of day that wasn’t fully planned but ended up being one of the best of the trip.

Morning: Thrifting, Coffee, and Hitting the Road

We started off slow, leaving The Grady Hotel in Louisville and making a quick stop at Goodwill so Bex could do a little thrifting (she never misses a chance) for Greenari Vintage (read | shop). After that, a necessary Starbucks run, and then we hit the road to Bardstown — bourbon’s beating heart.

Heaven Hill Distillery – Unexpectedly Incredible

We didn’t have a tour scheduled at Heaven Hill, and that turned out to be just fine. The campus is jaw-dropping — sprawling, elegant, and purpose-built for both bourbon nerds and casual visitors.

The visitor center was a standout. It included a beautifully curated museum-style walkthrough on Heaven Hill’s history: how it survived Prohibition, the devastating 1996 fire, and how it’s still family-owned — a rarity in the industry. Their portfolio is stacked too: Elijah Craig, Larceny, Henry McKenna, and more.

Five Brothers Bar & Kitchen – Trip Highlight

Without question, Five Brothers Restaurant inside Heaven Hill was the culinary and cocktail highlight of the entire trip. The food? Incredible. The cocktails? Next level. The setting was stylish but cozy, with views into the distillery campus. We could’ve stayed there all day. Honestly, if it weren’t out of the way from the rest of our stops, I would’ve come back the next day. It was that good.

After lunch, we browsed the gift shop and grabbed some bottles and merch before heading out.

Willett Distillery – Surprise Gem

Next stop: Willett, again with no tour booked — just a casual pop-in. And once again, we were blown away. The hospitality center is beautifully designed, modern but warm, and the bar/restaurant area had an open kitchen and a counter bar where we sat, sipped, and had a great chat with the bartender. The cocktails here were sophisticated and creative — definitely worth the detour.

James B. Beam Distilling Co. – A Whole New Perspective

We arrived early to Jim Beam in Clermont for our Basil Hayden Culinary Tasting Experience. Honestly, Beam was never a brand I took seriously — I always thought of it as a budget bourbon. But this visit totally changed my mind.

The grounds were beautiful, and the culinary tasting was a great showcase of how Beam is stepping up its game, especially through brands like Basil Hayden. It was classy, educational, and surprisingly impressive. I walked away with a newfound respect for their lineup.

Night Tour: Old Louisville Ghost Tour – Best Ghost Tour Yet

We made it back to Louisville just in time for our Old Louisville Ghost Tour, and it totally surpassed the one we did the night before. This one took us through the Victorian neighborhoods of Old Louisville, filled with ornate mansions and rich (and eerie) history.

We stopped at landmarks like:

Conrad-Caldwell House Museum
The Witches’ Tree (a bizarre local legend)
Filson Historical Society

The guide was top-notch and brought the city’s haunted history to life without making it feel hokey or over-the-top.

Back to The Grady

After a long day of sipping, snacking, ghost-chasing, and exploring, we headed back to The Grady Hotel to wind down. It was a full day — and somehow it all flowed seamlessly, from thrift stores to tiki bars to haunted mansions.

Bourbon Trail Trip – Day 4: Blanton’s Bottles, Female Founders, and Farewell Cocktails

Saturday, May 10th was meant to be a slow day with nothing on the books — until luck (and the waitlist gods) got us into Buffalo Trace. That gave this day a great anchor point, and what followed was a cascade of unplanned stops that turned into one of the most memorable stretches of the trip.

Morning Ritual: Thrifting & Coffee

We started the day with our now-traditional detours: Starbucks and Goodwill. Bex was on the hunt for vintage glassware and brass pieces for her Etsy store and did manage to snag a quirky wooden cat toilet paper holder. These little thrifting side quests didn’t yield much, but they were part of the charm of our mornings.

Buffalo Trace – Historic, Crowded, and Worth It

Even on a waitlist, Buffalo Trace is tough to get into — so we felt lucky when we scored a spot just days prior. The campus was buzzing, a true bourbon pilgrimage site, and the size and scope of the place reflected its legend status.

Tour Highlights:

Oldest continuously operating distillery in the U.S., dating back to the 1700s.
Learned about the massive 2024 flood, how it damaged warehouses, and how they’re rebuilding — including replacing warped concrete floors and retesting barrels.
Saw people hand-assembling Blanton’s bottles — easily the coolest behind-the-scenes glimpse.
Tasted: Wheatley Vodka, Buffalo Trace, E.H. Taylor Small Batch, and Sazerac Rye. The vodka acted as a palate cleanser, and each pour had a story — especially the caramel-forward notes in the Taylor and the peppery punch in the Rye.

We browsed the massive two-story gift shop, which had everything from collectible bottles to exclusive merch, but were bummed that there wasn’t a restaurant or cocktail bar onsite. Still, it was a great stop.

Bulleit Distilling Co. – Relaxed & Refreshing

Next, we headed to Bulleit. No tour, just vibes. The campus was small but stylish, and they offered craft cocktails in a laid-back indoor/outdoor lounge setting. We grabbed a couple drinks and picked up some limited-edition merch, happy to find something unique we couldn’t get elsewhere.

Jeptha Creed – Family Roots, Bloody Butcher Corn & Bourbon Hugs

On a whim, we made our way to Jeptha Creed, a female-led, family-operated distillery in Shelby County. It felt more like a cool farm brewery than a high-profile distillery — picnic tables, rocking chairs, and corn hole gave it a welcoming, community feel.

We sat at the bar for a private tasting and got a deep dive into their story:

Joyce and Autumn Nethery (mother and daughter) lead the operation, with Joyce as the master distiller.
They’re one of the only distilleries using 100% Bloody Butcher corn — dense, hard to grow, but rich in flavor and protein.
Their four-grain mashbill came from a road trip to Wisconsin, where Joyce and Bruce (her husband) created experimental batches — the “Great Compromise” between their favorite profiles.
Tasted bourbons ranged from “sweet heat” to “smoked leather baseball glove.” No lie.
We also tried Bloody Butcher vodka, moonshine, and their “Red, White & Bruce” three-corn blend.
We loved their vibe so much we stayed for cocktails, pretzel bread, fried pickles, and pizza.

This place felt like a hidden gem. Authentic, relaxed, and full of heart.

Michter’s – A Proper Send-Off

Back in Louisville, we ended the night at Michter’s. While we didn’t do the full tour, we did make it upstairs to their cocktail bar. The setting was polished and elegant, and the drinks were excellent — a perfect contrast to Jeptha Creed’s cozy feel. Michter’s is known for meticulous aging and blending, and it showed in every glass.

After a long day, we walked back to The Grady Hotel and called it a night, thankful for the unexpected magic this day brought.

Bourbon Trail Trip – Day 5: Wax Dips, Wooden Vats, and One Final Hug Goodbye

Sunday, May 11th marked the last leg of our bourbon adventure, but we definitely saved one of the best for last: a guided tour of Maker’s Mark Distillery in Loretto, Kentucky. While I’ve never been a Maker’s drinker, this stop, like many others on this trip, changed my mind. The campus was stunning, the stories were rich with history, and the hands-on experience made for a perfect send-off.

Arrival at Maker’s Mark – A Warm Welcome

We arrived at a picture-perfect property — lush greenery, black barns trimmed in signature red, and the kind of aesthetic that feels like a curated blend of history and hospitality. We even met Whiskey Jean, the distillery cat, lounging under a sign that read:

“I live here. Please let me sleep. I don’t like being touched.”

Of course, we did pet her, and she seemed fine with it.

Distillery Tour Highlights:

History & Innovation

The distillery dates back to 1805, originally operated by the Burks family.
In 1953, Bill Samuels Sr. and his wife Margie bought the property for $35,000. She deserves credit for the brand’s entire visual identity — from the bottle shape and red wax dip to the name Maker’s Mark itself.
Fun fact: she got the name from English pewter crafts, where artisans stamped their finest work with a “mark.”

The Mash & The Method

Maker’s uses a wheated bourbon mash bill: 70% corn, 16% soft red winter wheat, and 14% malted barley.
The grains are locally sourced and tested for quality before entering production.
A unique feature? Cypress wood fermentation vats — not for flavor, but for temperature control and tradition.

Distillation & Barrels

The 5-story copper column stills and steam cooking process were impressive.
Barrels are charred to a level 3 and filled at 110 proof, maturing over 6 to 8 years, hand-rotated for consistency — a process most distilleries gave up long ago.

Dipping Bottles & Maker’s 46

Of course, the highlight was hand-dipping our own bottles into their iconic 275°F red wax — a small act that made us feel part of the process. The wax seal is more than aesthetic; it’s a hallmark of craftsmanship, and the staff dip 60,000–80,000 bottles a day.

We also explored the cellar where Maker’s 46 is finished — 10 French oak staves added to fully matured bourbon and aged an additional 9 weeks at a constant 50°F. This makes for a smoother, richer sip that even non-bourbon fans would enjoy. And yes, we tried it all.

Tasting Flight:

Original Maker’s Mark (90 proof) – Classic caramel, vanilla, baking spice.
Maker’s 46 (94 proof) – Fruit-forward, super smooth, a crowd favorite.
Cask Strength (varies ~110–114 proof) – Big, bold, syrupy finish. Best for old fashioneds.
Private Selection: Toasted Marshmallow (111.1 proof) – Only sold at the distillery. Sweet, smoky, and delicious.

Final Thoughts

This was the perfect note to end on. Maker’s Mark gave us history, hands-on fun, a peek at the future of bourbon innovation, and a reminder of what makes Kentucky bourbon special. After a quick visit to the gift shop and a final look at the lake, we hit the road home — tired, happy, and maybe just a little bourbon wiser.