5 Pure Genius Cookie and Whiskey Pairings

There are pairings that, while a bit luxurious, are really about chemistry: pairing a bold Barolo with a perfectly seared ribeye, for example. Other pairings are exclusively indulgent, like pairing cigars and whiskey, or caviar and sparkling wine. Such pairings exist because they can.

The same goes for whiskey and cookies. It may not be the first combo that springs to mind, whether it’s because of the doubled-up calories, or the mixing of a dram with dessert. But wine pairs with chocolate beautifully, and arguably the flavor profiles are much more complex both the whiskey category and for cookies that can range from barely sweetened biscuits to spice-rich European throwbacks, to the sugar bombs found at Crumbl.

There are useful strategies to pairing whiskey and cookie to keep in mind. First, try and identify key flavor notes in the whiskey. Clove? Coffee? Oak? Heather? Use these top notes to guide your baked goods decisions, the way you might pair wine and cheese. The second also comes from the wine world. If you’re sipping a sweetened whiskey, like BSB brown sugar bourbon or Skrewball, make certain your cookies aren’t sweeter than your whiskey, otherwise you run the risk of throwing off the whiskey flavors. Save the extra-sugary treats for classic oaky, tannic whiskeys. Consider the whiskey expressions below to be guidelines for your own exploration into indulgence.

Woodinville Whiskey Co. Founder’s Find & Peppermint Cocoa Cookies

Woodinville Whiskey and Pepperidge Farm Peppermint Cocoa photo credit Robert Haynes-Peterson

Woodinville Whiskey, located northeast of Seattle, is firmly embedded in the metro area’s wine and spirits tasting neighborhood, where you’ll find over 130 tasting rooms, distilleries, breweries, and more. The brand’s signature small-batch bourbon has a high-corn mash bill (72%) and is dark and rich with a hint of sweetness. While most expressions are distilled on site, this one is the brand’s first “sourced discovery,” and was released as part of the distillery’s annual event where fans wait overnight to be the first to purchase Woodinville’s Harvest Release.

Founder’s Find reportedly came about when Woodinville co-founder Orlin Sorensen was working on another project. In the process, he discovered a “forgotten” 12-year whiskey aged in reconditioned charred barrels and made from a “bourbon mash,” and decided to bottle it as the brand’s first sourced whiskey.

$129, 53.5% ABV

Why it works: The extra aging on this whiskey beautifully rounds out the bumpy edges of a higher-proof product (it’s not officially a bourbon, since it was aged in previously used barrels). The dark amber liquid has a viscous heaviness, a slight sweetness, and hints of coffee, baking spices, and a bit of dark chocolate. Peppermint cocoa cookies find a balance between sweet and bitter, with the dry notes of cocoa and dark chocolate interrupted with spicy bites of peppermint. The Pepperidge Farm version I paired up was a holiday release, but you’ll find similar cookies from Trader Joe’s, Rustic Bakery, and Nestle Tollhouse.

Jack Daniel’s & Oreos

My dad worked the night shift, coaxing the regional newspaper out the door. He left for work as I got home from school and returned home after I went to bed. On occasion, I’d wake up at 2 or 3 a.m. and find him in his recliner, strumming on hs guitar, sipping Jack Daniel’s and munching Oreos. We’d chat about life, the universe, and everything while he strummed and sipped.

Back then, according to Jack Daniel’s master distiller Chris Fletcher, the core (and only) expression, Old No 7, was actually an allocated whiskey, because they couldn’t make it fast enough. These days, you can get Old No 7 just about anywhere, but Fletcher and his team have expanded the portfolio significantly to limited edition releases such as Distillery Series and extra-aged expressions. The most recent release, the company’s first 14-year aged expression in over a century, is composed of select barrels of the same whiskey as Old No 7 that are brought down from the hottest, highest levels of the rickhouses down to floor level to slow the aging process in its final years. The results are stunning.

Old No 7 $20, 40% ABV | 14-Year-Aged $150, 63% ABV

Why it works: Because it makes me think of my dad, that’s why it works. Beyond that, both Oreo and the core Jack Daniel’s are familiar and not overly complex products. Like a mainstream Chardonnay and a mild cheddar, neither require a lot of concentration, they just make for a pleasant evening.

But now that both Jack Daniel’s and Oreo have expanded their offerings, the opportunities for experimentation are multitude. I paired JD’s 14-Year with Oreo’s limited release Post Malone Taste Twist variation. The whiskey is in a class all its own, noticeably darker than its 10- and 12-year-old sister expressions. You’ll get a ton of confectionary notes like dark molasses, chocolate, and a cigar tobacco long finish with leather top notes. There’s a rich caramel cream aromatic that itself evokes filled cookies. Pairing it with Malone’s version of the Oreo with its swirled cream of salted caramel and shortbread works wonderfully, though the cookie is so rich and sweet, just a couple will do.

Glenmorangie 12 Year & Walker’s Shortbread

The Glenmorangie is a Highland single malt whiskey distilled on the coast in northern Scotland under the watchful eye of the legendary Dr Bill Lumsden, a chemist-turned-distiller. The extra-tall stills at the distillery contribute to the nature of the distinctively creamy single malts with hints of citrus, honey, and vanilla. The 12-year expression–the brand’s flagship–was recently reimagined to soften and round out the liquid, highlighting the single malt’s peach, orange, and honey notes and silky texture, earning the expression itself winning Individual International award at the 2024 New York International Spirits Competition, while the distillery received two gold medals.

40% ABV, $50

Why it works: Scotland excels at evoking the ecosystem and aura of the land in its foods, from Highland heather and honey to briny Islay peat mud. So it’s no surprise that the Scotch and the Scottish cookie share overlapping flavor notes. The buttery cookies with a hint of floral and just a touch of citrus pair beautifully with the whisky, encouraging enjoying a dram and a few cookies while watching the sunset from a deck or Scottish hilltop.

If you’re a fan of vanilla wafers on your ice cream, consider one of Glenmorangie’s most recent releases, A Tale of Ice Cream. Part of the company’s Tale series (there’s also been A Tale of the Forest and A Tale of Cake), it was deliberately designed to evoke an ice cream menu and is the first time Lumsden and his team have blended Glenmorangie component whiskies aged in high-vanillin casks with those aged ex-bourbon casks. Yum!

Old Forester 1897 Bottled-in-Bond Bourbon & Pirouette Wafers

Old Forester 1897 Bottled-in-Bond Bourbon and Pirouette Wafers photo credit Robert Haynes-Peterson

Bottled-in-bond whiskies have a long history but were sort of in the background as a category until the past decade. The 1897 Bottled-in-Bond Act was intended to protect the public from deceptive whiskey producers. A spirit labeled as bottled-in-bond ensures it’s made from the ingredients required for a specific spirit, at one distillery, and distilled in one distilling season. Old Forester claims to have marketed the first bottled-in-bond whiskey back in 1897, and this expression celebrates that claim. Cementing its place in history, Old Forester opened a 70,000-square-foot distillery on Louisville’s Whiskey Row (where the brand began) in 2018.

Old Forester’s bourbons are classic, old-school spirits with a balance of spicy and sweet, with a fruit-and-toffee bold nose. You’ll get the alcohol up front (in a good way), even in lower-proof expressions. The BIB also offers up hints of dark fruit, oak, and a crisp clove-nutmeg spice note, with a long, slightly sweet finish.

50% ABV, $50

Why it works: Pirouettes are a classic central-European cookie made from the basics: flour, eggs, vanilla, butter, and confectioner’s sugar. They’re lightly sweet, but more of a classic biscuit than a super-sweet cookie. The crunchy rolled wafers work beautifully with a straightforward whiskey, pulling out the whiskey’s sweet and spice notes. I opted for the last of my Old Forester 150th Anniversary bottle, with noticeable banana bread and toffee-vanilla overtones. And of course, you may want to opt for creme-filled or chocolate-covered pirouettes if you’re feeling particularly saucy.

Angel’s Envy Cask Strength Straight Bourbon 2024 & Biscotti

Angel's Envy Cask Strength 2024 and Biscotti photo credit Robert Haynes-Peterson

Angel’s Envy has become known over the years for its tradition of finishing straight bourbon in port casks. The technique softens the hard edges of the whiskey and imbues it with subtle notes of candied fruits, stewed plum, and dark firewood. The technique has earned the brand legions of diehard followers who eagerly await the special annual release of a cask-strength version.

The 2024 cask strength release (Angel’s Envy’s 13th annual release) changed things up a bit with the addition of whiskey finished in tawny port barrels, along with the traditional ruby port barrel-finished component whiskeys. The result is a rich, robust bourbon overlain with additional toffee, caramel, almond, oak, dark fruit, and a hint of light cigar smoke. It’s so good, it earned a Double Gold Medal at last year’s New York International Spirits Competition. Just over 23,000 bottles were released.

59.4% ABV, $230.

Why it works: Honestly, it’s a match made in heaven. The barely sweet, crunchy biscotti–with its thin layer of bittersweet dark chocolate and hints of almond and licorice–pairs beautifully with the rich, complex notes of the bourbon, without drowning it in sugar. I took things up a notch and paired it a second time with Nonni’s salted caramel biscotti. The addition of caramel, toffee, and a hint of salt creates a tantalizing back-and-forth between cookie and whiskey on the palate, without coming off as over-sweet.

Want to have your cookie and drink it too? Orkney Islands-based Highland Park Scotch whisky came up with the Tough Cookie, a frothy, coffee cocktail combining all the best things in one drink. Use whatever cookie you wish for the topping, but we suggest a non-chewy version for extra crunch and texture.

Tough Cookie Cocktail

1.5 oz Highland Park 12-Year Single Malt

1.5 oz Cold Brew Coffee

.5 oz Cookie Butter

.5 oz Simple Syrup

Crumbled Cookies (Vanilla Wafers, Biscotti, or Shortbread work well)

Salted Whipped Cream

In a shaker with ice, add whisky, cold brew, and cookie butter. Shake well and strain into a highball glass filled with fresh ice. Top with salted whipped cream and cookie crumbles. Serve with a straw and ice cream spoon.