Tasting Tuesday Wednesday: A Christmas “Best Of” Bourbon Showdown

Twelve bottles. Four flights. One clear winner.

Every Christmas trip to the mountains seems to come with its own quiet rituals. Some are expected—family meals, familiar roads, the same views you’ve seen a hundred times before. Others evolve over time. This year, mine came in the form of a small bourbon carrier packed with twelve bottles that represent the very best of my shelf.

There was no theme beyond quality. No price ceiling. No attempt to crown a “budget king” or chase hype. The goal was simple: taste the bourbons I genuinely enjoy the most and see how they stacked up against one another. I sampled them in four flights of three, selected a winner from each group, and then let the final four decide the outcome.

What surprised me most wasn’t which bottle won—some things are predictable for a reason—but how strong the field was from top to bottom. There were no weak pours here. Just different expressions of what great whiskey can be, depending on mood, proof, and palate. What follows isn’t a lab report or a scoring exercise. It’s simply one bourbon lover’s snapshot of a memorable tasting.

🥃 First Group

Wilderness Trail

Color: Medium amber
Nose: Rich caramel, vanilla, toasted oak
Palate: Butterscotch, nutmeg, citrus zest
Mouthfeel: Medium-bodied
Finish: Light chocolate and oak linger gently

Four Roses OESO

Color: Deep amber
Nose: Ripe red fruit, brown sugar, chocolate, light oak
Palate: Fruit-forward caramel, cinnamon, dark chocolate
Mouthfeel: Silky and rounded
Finish: Chocolate deepens with satisfying oak

Jack Daniel’s Single Barrel Barrel Proof Rye

Color: Solid mahogany
Nose: Chocolate, caramel, banana, nutmeg
Palate: Chocolate-covered caramel, baking spice, banana—remarkably bourbon-like for a rye
Mouthfeel: Viscous and rich
Finish: Long, decadent, and spiced

Result:
🥇 Jack Daniel’s Barrel Proof Rye
🥈 Four Roses OESO
🥉 Wilderness Trail (a strong bottle, just facing stiff competition)

🥃 Second Group

Jack Daniel’s Heritage Barrel

Color: Burnished copper
Nose: Vanilla, caramel, toasted oak
Palate: Sweet rush of caramel and brown sugar with light spice
Mouthfeel: Medium, smooth
Finish: Brown sugar dominates

Rebel Single Barrel (Kyle Busch Selection)

Color: Dark amber
Nose: Cherries, caramel, vanilla
Palate: Cherry jubilee, vanilla, caramel
Mouthfeel: Thick and coating
Finish: Sweet, rich, and very satisfying

Maker’s Mark 2024 Heart Release

Color: Dark and inviting
Nose: Dark chocolate, toffee, oak, subtle berries
Palate: Oak arrives early but integrates with dark chocolate, molasses, and black cherry
Mouthfeel: Creamy and rich
Finish: Long, with oak, chocolate, and fruit in balance

Result:
🥇 Maker’s Mark Heart Release
🥈 Rebel Single Barrel
🥉 Jack Daniel’s Heritage Barrel (still excellent, just not at its peak here)

🥃 Third Group

Kentucky Rambler

Color: Deep amber
Nose: Cherry, caramel, spice
Palate: Bold cherry, caramel, spice
Mouthfeel: Surprisingly calm for 124 proof
Finish: Assertive and warming

Copper & Cask

Color: Deep copper, nearing mahogany
Nose: Maple, brown sugar, nutmeg, caramel
Palate: Cinnamon, nutmeg, caramel, honest oak
Mouthfeel: Velvety and rich
Finish: Warm and lingering with caramel and spice

Doc Whiskey

Color: Deep copper, darker than expected for its age
Nose: Earthy at first, then vanilla, baked fruit, cocoa
Palate: Caramel, cocoa, vanilla, allspice
Mouthfeel: Creamy and full
Finish: Long, warm, cocoa and apple

Result:
🥇 Doc Whiskey
🥈 Kentucky Rambler
🥉 Copper & Cask

🥃 Fourth Group

Early Times

Color: Golden amber
Nose: Roasted peanuts, cinnamon, soft tree fruit
Palate: Caramel, apple, cinnamon, vanilla
Mouthfeel: Lighter but respectable
Finish: Mid-length, brown sugar and oak

Far Better Ultra Small Batch

Color: Deep copper
Nose: Proof-forward at first, then oak, cinnamon, vanilla
Palate: Oak, chocolate, brown sugar, savory spice
Mouthfeel: Creamy and surprisingly composed for 141.8 proof
Finish: Sweet, brown-sugary, and deeply satisfying

Smooth Ambler Old Scout

Color: Rich amber
Nose: Leather, cardamom, caramel
Palate: Cherries, banana, brown sugar, nutmeg
Mouthfeel: Oily and coating
Finish: Long, fruity, and sweet

Result:
🥇 Far Better
🥈 Smooth Ambler Old Scout
🥉 Early Times (outgunned here, but unbeatable at its price)

🏆 The Final Four — Overall Results

4️⃣ Maker’s Mark Heart Release
Rock-solid and delicious, but its trademark simplicity keeps it from separating from the pack at this level.

3️⃣ Doc Whiskey
The overachiever. Beautiful flavors and incredible value, but it runs out of complexity against elite competition.

2️⃣ Far Better Ultra Small Batch
The sleeper hit. Hazmat proof with real elegance and depth. This bottle deserves far more attention than it gets.

🥇 Jack Daniel’s Barrel Proof Rye
No surprises here. It transcends categories—bourbon, rye, Tennessee whiskey—and consistently proves why it belongs at the top of so many lists. The best whiskey of Christmas, and arguably the best thing on your shelf.

At the end of the night, the results told a familiar story—but with a few important footnotes. Yes, the heavy hitters rose to the top. Yes, experience, proof, and depth still matter. But value, personality, and surprise mattered too. Some bottles punched well above their weight. Others reminded me why consistency is a virtue in its own right.

What this tasting reinforced is something I keep learning over and over again: great bourbon doesn’t exist in a vacuum. Context matters. Mood matters. Even the order you taste things in matters. A $20 bottle can impress when expectations are low, and a celebrated release can stumble when the bar is set high.

And that’s part of the fun. Bourbon isn’t about chasing perfection—it’s about discovery, revisiting old favorites, and occasionally being stopped in your tracks by a bottle you didn’t see coming. This dozen did all of that. And if Christmas had to crown a winner, it did so honestly.

Here’s to good whiskey, good company, and the joy of finding something familiar—and something new—in the same glass. 🥃