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Food & Drink

Tasting Winchester's New Kentucky Straight and Double Oaked Whiskeys

Tasting Winchester's New Kentucky Straight and Double Oaked Whiskeys

Hook & Barrel reviews Winchester’s new Kentucky Straight and Double Oaked Bourbons, exploring how the iconic American brand’s 150-year legacy translates into the whiskey world. From smooth cocktail-ready character to richer double-oaked complexity, we taste both new offerings and share a favorite bourbon cocktail recipe to try at home.

By Niki Morrison
Published Jun. 1, 2026

We poured the new Kentucky Straight and Double Oaked bourbons to see whether 150 years of Winchester tradition could carry from the field to the glass.

A bottle of Winchester Kentucky Straight Bourbon Whiskey and a bottle of Winchester Double Oaked Kentucky Straight Bourbon Whiskey on a wood table in a rustic setting

Few things are more fun than an impromptu bourbon tasting on a random Thursday evening, so when I received Winchester’s first foray into the world of spirits, I invited my best friend over for a cocktail-hour tasting. We’ve both had our share of bourbons over the years, so it’s always fun seeing what we think of a new brand. I was particularly interested in seeing how Winchester’s 150 years of history and strong ties to American tradition and outdoor culture would translate to my favorite spirit.

As it turns out, there's more to the story than a firearms brand putting its name on a bottle. The bourbons are produced by Model 1866 Distillery, named for Winchester's founding year and created to connect the brand's heritage to its new whiskey venture. Model 1866 grew out of Ugly Dog Distillery, a company founded by avid bird hunters and outdoorsmen whose culture revolves around many of the same traditions that have long been associated with Winchester. That shared background helps make the partnership a natural fit. Winchester Bourbon's CEO David Salmon says, “Great bourbon starts the same place as a great hunt does, in the field.”

Winchester Kentucky Straight Bourbon Whiskey

We started with Winchester Kentucky Straight Bourbon Whiskey, which is priced around $45. It poured a rich amber color in both the bottle and the glass. The aroma brought light spice and a touch of smokiness. After the first sip, we agreed it would make a great Gold Rush cocktail: bourbon, honey syrup, and fresh lemon juice. That’s exactly how we ended up enjoying it.

Two bottles of Winchester bourbon with a Gold Rush cocktail
Winchester Kentucky Straight Bourbon Whiskey made an excellent Gold Rush.

Winchester Double Oaked Kentucky Straight Bourbon Whiskey

Next up was the Winchester Double Oaked Kentucky Straight Bourbon Whiskey, which pours a darker amber with richer copper tones. The oak shows up right away with smoky notes, spice, a hint of caramel and a more layered profile overall. Priced at $65, it's a worthwhile upgrade. It’s a bit richer on the palate and finishes with some sweetness and a hint of nuttiness.

Turns out we weren't the only ones enjoying it in different ways. As Hook & Barrel CEO John Radzwilla put it: “I drank it neat and then, out of sacrilege, added Coke. I truly just enjoyed it while I was cooking a wild game dinner.


Hook & Barrel in a Glass

Hook & Barrel recommends this bourbon-forward twist on the Manhattan, a worthy alternative to the increasingly popular espresso martini:

A Revolver Cocktail in a coupe glass

The Revolver

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