Woodford Reserve Double Double Oaked Bourbon

 More Oak, More Bourbon… or Just More Money?

I’m a big fan of Woodford Reserve Double Oaked. At around $46 a bottle, it has always struck me as one of those bourbons that delivers far more than its price would suggest.

So when Woodford Reserve Double Double Oaked first hit the shelves, I was intrigued.

The thinking seemed simple: I like Double Oaked… so wouldn’t twice the oak be even better?

Well… sort of.

The first time I tried Double Double Oaked, I thought it was very good—rich, sweet, smooth and loaded with oak. But was it better than Double Oaked?

Honestly, I wasn't convinced.

Then there was the little problem of the $169 price tag.

At that price, my expectations were pretty high. After all, I could buy nearly four bottles of standard Double Oaked for the price of one bottle of Double Double Oaked. That's a lot of bourbon to ask one bottle to compete with.

Fast-forward to today.

Bourbon prices have softened, and Double Double Oaked has become considerably easier on the wallet. This time, I picked up a bottle for $69.

And you know what?

It tastes better at $69.

Okay, maybe the bourbon hasn't changed—but my expectations certainly did.

Double Oaked vs. Double Double Oaked

What's the Difference?

(notes from Woodfordreserve.com) The basic idea behind both expressions is similar. Woodford Reserve Double Oaked begins with bourbon that has already matured in its original barrel and then receives additional maturation in a second, specially toasted barrel. Double Double Oaked takes that concept even further.

The biggest distinction is the additional time spent in the second barrel. That extended secondary maturation allows the whiskey to take on even more of those rich oak-derived flavors.

And you can taste it.

More toasted oak. More caramelized sweetness. More vanilla. More of that dessert-like character that makes Double Oaked such an approachable bourbon. But more oak doesn't automatically mean better bourbon.

That's where the tasting comes in.

Production & Specs

• Mashbill: 72% corn, 18% rye, 10% malted barley

• Initial Aging: Approximately 5–7 years

• Secondary Aging: Extended maturation in a heavily toasted, lightly charred second barrel

• Proof: 90.4 (45.2% ABV)

The Oregon Man Review

This is not a bourbon I want to rush. Double Double Oaked is built for the slow pour—the kind of bourbon that deserves a good glass, a comfortable chair and an hour that isn't going anywhere. So, in true Oregon Man fashion, I slowed things down.

I picked the music: Kentucky Woman” by Neil Diamond.

I selected a quality cigar - The Padrón 1964 Anniversary Series

Then I poured myself a glass, sat back and gave the bourbon the attention it deserved.

The Nose

The first impression is unmistakably Woodford. Sweet oak leads the way, followed by vanilla, brown sugar and a touch of toasted marshmallow. There's a richness here that immediately separates Double Double Oaked from a more traditional bourbon. The oak is noticeable—but it isn't harsh.

The Flavor

This is where Double Double Oaked makes its case. The first sip brings a wave of brown sugar, toasted oak and marshmallow, followed by vanilla and a gentle caramel sweetness.

There is definitely more oak than the standard Double Oaked, but the additional wood doesn't completely overwhelm the sweetness. Instead, it creates a deeper, darker flavor profile. For me, the real appeal is the balance between the sweetness of the bourbon and the roasted character of the oak.

I Like the Lower Proof

Double Double Oaked comes in at 90.4 proof, or 45.2% ABV.

Some bourbon enthusiasts will tell you they want more proof. More alcohol. More intensity. More punch.

I'm not one of them.

I appreciate higher-proof bourbon from time to time, but I don't particularly enjoy the alcohol burn that can come with it. At 90.4 proof, Double Double Oaked has enough weight and flavor to be interesting without beating you over the head. It's smooth, approachable and easy to sip. And for the kind of evening I'm describing here, that's exactly what I want.

So… Is It Better Than Double Oaked?

Here's the tricky part.

Is Double Double Oaked better than Double Oaked?

I'm still not sure, It's certainly different.

The additional maturation brings more oak, more richness and a deeper flavor profile. But standard Double Oaked remains one of my favorite values in bourbon. At roughly $46, Double Oaked is incredibly hard to beat.

At $169, I had a hard time making the case for Double Double Oaked.

At $69? That's a completely different conversation.

Is It Worth Buying?

Absolutely—at the right price.

For me, that price is around $60-$70.

At that price, Double Double Oaked becomes a very compelling bottle. You're getting a richer, more oak-forward version of a bourbon I already enjoy, without feeling like I need to save the bottle for a presidential inauguration.

Cocktail Worthy?

Absolutely.

Although I prefer drinking Double Double Oaked neat, it has enough character to stand up beautifully in classic bourbon cocktails. I'd particularly recommend it in an Old Fashioned or a Bourbon Manhattan.

The extra oak and sweetness can add another layer of depth to the cocktail without requiring a complicated recipe. But honestly, if I'm going through the trouble of finding a bottle at $69, my first pour is probably going to be neat.

The Oregon Man Verdict

Woodford Reserve Double Double Oaked

Proof: 90.4

Style: Rich, sweet, oak-forward - best enjoyed: Neat, with time and Neil Diamond singing “Kentucky Woman” and lighting up the Padron 1964 Anniversary Series cigar that can stand along side the oak.

Value: ⭐⭐⭐⭐½ at $69 / ⭐⭐½ at $169

Double Double Oaked is a fascinating bourbon because it raises a question that bourbon drinkers wrestle with all the time:

When does more become too much?

For me, the answer is the original price I paid $169

But for $100 less, heck yeah, the equation changes.

Does it taste better because I paid less?

Probably not. But sometimes the price of the bottle changes how we experience what's in the glass and at $69, I'm not comparing Double Double Oaked to four bottles of Double Oaked.

I'm simply sitting back, listening to some Neil Diamond, enjoying a good cigar and thinking:

"Yeah… this is pretty damn good bourbon".

The Oregon Man