As some of you know, I’m in the early stages of building a new blind bracket challenge, which means I’ve been re-tasting a lot of bottles—some favorites, some forgotten, and a few that deserve a fair second hearing.

One of those bottles is Woodford Reserve Double Oaked.

A Little Background

Woodford Double Oaked starts life as standard Woodford Reserve, then gets a second maturation in a heavily toasted, lightly charred new oak barrel. That extra time in fresh oak is meant to amplify sweetness, richness, and depth—pushing the bourbon firmly into dessert territory.

When I first bought this bottle, though, I wasn’t sold. The oak felt too oaky, crowding out the balance I usually look for. It didn’t quite hit my sweet spot, so it went back on the shelf for a while.

Fast forward to this week.

The Re-Taste

Tasted blind as part of the competition, this was not the bourbon I remembered. Time—and maybe my own evolving palate—has been kind to it. What showed up in the glass was confident, layered, and remarkably composed.

Tasting Notes:

• Color: Solid mahogany

• Nose: Brown sugar, nutmeg, crème brûlée

• Palate: Rich and buttery, with waves of caramel, chocolate, and warming spice taking turns rather than competing

• Mouthfeel: Full and lush, with flavors that linger long after the sip—no hurry to leave

I won’t engage in hyperbole, but this was pretty great.

Looking Ahead

I have no idea how far this will go in the upcoming bracket—blind tastings have a way of humbling predictions—but based on what I tasted earlier this week (and again tonight), this bottle has the potential to go deep.

This is very much a dessert-in-a-glass bourbon. It’s indulgent without being ridiculous, and the price—while not cheap—isn’t outrageous for what you’re getting. Safe to say, this one will be seeing more time in my glass over the coming weeks and months.

Sometimes, the bourbon doesn’t change.
We do.