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  • 11/24/2025

Best HOLIDAY Whisky Cocktails to Celebrate The Season

It’s that time of year: the holiday season unfolds, the winter whisky cocktails are poured, and the good times linger just a bit longer. Warming, smooth, and comforting, Pendleton® Whisky is the best whisky for holiday cocktails and moments you’ve earned.

Over here in the American West, we have our own way of celebrating the holidays, from toasting traditions to how we drink bourbon. But this year, let’s shake things up a bit.

Traditional yet one-of-a-kind, these are a few of our favorite holiday whisky cocktails that will pair with any way you celebrate the season. Let’s get into it.

Four Holiday Whisky Cocktails for the Winter Season

These aren’t your average cranberry whisky cocktails. This is our roundup of some of the best whisky drinks for winter and autumn.

Cinnamon Re-Ride: For Cozy Holiday Nights 

There’s no place like home for the holidays, especially with this easy holiday whisky drink on hand. Featuring a beloved blend of cinnamon and almond flavor, this recipe brings out the spiced fruit notes of Pendleton® Whisky Original in a delightful way. So wrangle a friend or two and get the fire going. This crafted spiced whisky drink is the perfect way to come together and toast to life’s simple pleasures.

Holiday Flavor Profile: Warm, cozy, rich 

Presentation Tip: Craft in a rocks glass and add a cinnamon stick garnish for an extra comforting yet bold sip.

Holiday Food Pairing: Pair with other spiced dishes, such as iconic holiday desserts like apple pie, spiced cookies, cinnamon rolls, or even something savory like glazed ham or roasted nuts.

Cowboy Gold Rush: For Hosted Dinner Celebrations

This bourbon holiday cocktail is keeping spirits bright and spiced. This rings especially true with Cowboy Gold Rush, a delicious fusion of flavors that deserves a spot amongst other whisky cocktails for Thanksgiving dinner. This cocktail works exceptionally well for dinner celebrations when you’re ready to break out the good stuff, like Pendleton® 1910 Bourbon. The smooth, honeyed nature of this cocktail is the ultimate warm welcome for any guest, presenting a balance between sweetness and brightness in every sip.

Holiday Flavor Profile: Bright, honeyed, comforting

Holiday Food Pairing: Thanks to the combination of rich bourbon, bright honey and fresh lemon, this cocktail complements well with roast turkey, herb-baked chicken, as well as aged cheeses like gouda or sharp cheddar. From a grazing buffet to a full-seated dinner with the works, this is one delicious addition to your hosted cocktail lineup.

Presentation Tip: Pour in a sophisticated rocks glass garnished with a lemon peel to impress guests. 

Backwoods Punch: For Large Festive Celebrations 

Holiday punch with whisky or holiday whisky with a punch? We’ll let you be the judge. We have a few ideas on how to host a holiday party, and Backwoods Punch should be part of that. Whether you’re fulfilling the role of host or bringing a little something to the potluck, this recipe is one of the best whisky cocktails for parties. Made with the unmistakably smooth Pendleton® Whisky 1910 Rye, it’s how all celebrations should taste.

Holiday Flavor Profile: Lively, bold, nostalgic

Holiday Food Pairing: Curate the table spread of your holiday dreams with a buffet featuring rich, creamy cheese boards, bold and savory pies, or mini beef sliders to impress your guests.

Presentation Tip: Punch bowls are the perfect vessel for serving at parties. Add cranberries and citrus slices as a flavorful finishing touch.

Pro Tip: Never go to a party empty-handed. Gift a bottle of Pendleton® Whisky 1910 Rye, offering the perfect opportunity to craft an inspired Christmas Old Fashioned if the punch runs low.

Midnight BOULEVARDIER: For Intimate Holiday Get-Togethers

It’s the season for togetherness. So it’s only right that we bring together two iconic flavors in this cocktail: Pendleton® Whisky and Campari. Midnight Boulevardier is crafted with Pendleton® Whisky Midnight, a spirit inspired by our Western way of living, and shines even brighter within this unexpected Negroni-like taste profile. Ideal as a Thanksgiving or Christmas whisky drink, for when the table is set and you’re ready to enjoy some good company.

Holiday Flavor Profile: Thoughtful, rich, timeless

Holiday Food Pairing: Set your table — and whisky tasting — up for success by pairing dishes with notes of cherry and spice. Dark chocolate, fruit tarts, or creamy blue cheeses also bring out bold nuances within this cocktail.

Presentation Tip: For a polished and classic look, serve in a coupe glass and top with a cherry.

Discover More of The Best Whisky Drinks for Winter with Pendleton® Whisky

The holiday season is the perfect time to revel in the year’s triumphs. Your season deserves a spirit that’s more than just a pour, but a reward. Whether you’re cozying up by the fire with a whisky drink or testing out one of these winter whisky cocktails, your new holiday tradition awaits.

We’ll cheers to that. Bring the spirit of the holidays home. Get your bottle of Pendleton® Whisky today and try these festive cocktails this upcoming season.

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