25 stops. Dozens of pours. These were the ones I’ll never forget.

This summer, I finally made my first trip to the Bourbon Trail — and it lived up to every drop of hype. Over five days, our crew made 25 stops across Kentucky and Tennessee, sampling everything from straight-from-the-barrel ryes to legendary limited releases. We did distillery tours, thieved from barrels, conquered blind tastings, and enjoyed some unforgettable pours along the way.

I couldn’t begin to count how many whiskeys I tasted during the trip. But I can tell you which 13 stood out above the rest — including one special pour I crafted myself during a Friday night blind.

Here’s the countdown, starting with a blend that came straight from my home shelf but held its own in a strong field.

#13. “Baby Birthday Bourbon” – My Personal Old Forester Blend (100 Proof)

On Friday night, I hosted a blind tasting at our Louisville hotel featuring only 100-proof Old Forester expressions. To round out the lineup, I proofed down a custom blend I’d made from four bottles on my shelf: Single Barrel, 1897 Bottled in Bond, 1910 Old Fine Whiskey, and 1920 Prohibition Style. That blend — affectionately nicknamed “Baby Birthday Bourbon” — ended up winning the blind. It captured the best of Old Forester: rich caramel, baking spice, oak, and a sweet finish, all wrapped in a balanced 100-proof package. It didn’t reach the complexity of the real Birthday Bourbon, but it sure earned its place on this list.

#12. Four Roses OESO Single Barrel (100 proof)

A polished, fruit-forward recipe that leaned into plum, vanilla, and soft spice. It was a pleasant pour, but on a trip full of standouts, this one simply didn’t demand center stage. Still, it showcased Four Roses’ finesse and complexity — just a little too subtle for this lineup.

#11. Buzzard’s Roost Signature Double Oak

I came home with this one — and with good reason. The double oak brought rich layers of vanilla, cinnamon, and toasted wood. It’s a bottle that rewards slow sipping and quiet evenings, and while it didn’t crack the top 10, it left a lasting impression.

#10. High West Midwinter Night’s Dram

This one took top honors in Tim’s Thursday night blind tasting. It drinks like holiday cheer in a glass — with mulling spice, port wine richness, and just enough rye kick to keep it grounded. Theatrical and warming, like a Christmas Eve fireplace story.

#9. Old Forester 117 Series 1910 Extra Extra Old

Sweet, smoky, and decadent — like liquid s’mores. Caramelized sugar, toasted oak, and a marshmallow char came through with every sip. One of the most dessert-like pours of the trip, and yes, I brought this one home.

#8. Barrel-Strength Rye (Thieved at Bardstown Bourbon Company)

There’s just something about pulling a sample straight from the barrel with a whiskey thief. This rye came alive with spearmint, citrus zest, and cracked black pepper. Raw and vivid. I couldn’t bring the barrel home, but I snagged the next best thing — a bottle of Bardstown’s Origin Series Rye.

#7. Old Forester 117 Series Bonded

Big, bold, and full of character. This one brought dark toffee, leather, and a peppery backbone that stood out in our post-tour flight. A reminder that bonded whiskey, when done right, can still deliver knockout punches.

#6. Larceny Barrel Proof (Two Variants: Evan Williams & Heaven Hill Y-Series)

I tasted this twice — once at the Evan Williams Experience and again at Heaven Hill, where I bottled my own. Wheated warmth, brown sugar, and cinnamon spice made this a consistent crowd-pleaser. High proof without high drama.

#5. Michter’s 10-Year Straight Bourbon

Refined and elegant, this pour whispered instead of shouting. Deep caramel, fig, and oak layered beautifully in a silky sip. It didn’t overwhelm — it impressed with restraint.

#4. Yellowstone Toasted Barrel Bourbon

From the last available barrel before this release is gone for good. This pour hit like a campfire dessert: toasted marshmallow, spiced oak, caramel, and orange peel. A little rustic, a little refined — and yes, I brought it home.

#3. Far Better Cask Strength Bourbon

North of 140 proof and absolutely bursting with jammy red fruit, baking spice, and cola. It was wild and unforgettable but in a charming way — like the house band at a Nashville honky-tonk that just blew the roof off. It was bold enough that I had to leave it behind in Tennessee (thanks, federal proof laws). Thankfully, Scott is bringing it home for me.

#2. Jack Daniel’s 14-Year

This one was our reward after Austin’s blind tasting on Wednesday night, and it felt like a celebration in every sip. Molasses, cherry cola, tobacco, and oak danced together in a deep, balanced pour. Maturity without pretension — Tennessee whiskey at its finest.

#1. Old Forester Birthday Bourbon

The crown jewel of the trip. Elegant, layered, and utterly memorable. Cherries, toasted almond, custard, and spice all mingled in a pour that felt like a master class in blending and aging. This wasn’t just a great bourbon — it was a moment. And in a trip full of them, this was the one I’ll keep talking about.

Final Thoughts

Every distillery has its own story, but what tied this trip together was the shared experience — the laughs, the debates, the blinds, the surprises, and the occasional whiskey that stopped us in our tracks. I brought home bottles, memories, and a deeper appreciation for the craft and culture of bourbon.

This was my first Bourbon Trail trip. I can already tell it won’t be my last.