18 Best Winter Bourbon Cocktails to Try

The Vanilla Cinnamon Old Fashioned is a cozy twist on the classic cocktail, perfect for winter nights and festive celebrations. It combines the rich warmth of bourbon with the gentle sweetness of vanilla and the comforting spice of cinnamon.

Each sip is smooth, aromatic, and perfectly balanced, offering both depth and sweetness without being overpowering. The cinnamon adds a subtle kick that pairs beautifully with the bourbon’s caramel notes, creating a drink that feels both familiar and special. Whether you’re relaxing by the fire or entertaining guests, the Vanilla Cinnamon Old Fashioned is a simple yet elegant winter favorite.

The Hot Buttered Bourbon is the ultimate winter drink, bringing warmth and comfort to cold evenings. It blends the deep, rich flavor of bourbon with hot apple cider and a mix of cozy spices for a smooth and soothing cocktail.

The addition of butter and honey gives it a silky texture and a gentle sweetness, while cloves and cinnamon fill the air with a comforting aroma. Each sip feels rich, spiced, and perfectly balanced. Garnished with a cinnamon stick, this drink is ideal for fireside gatherings, holiday celebrations, or simply winding down after a long, chilly day.

The Winter Honey Old Fashioned is a rich and comforting cocktail that captures the cozy spirit of the season. It brings together the smooth depth of bourbon with the gentle sweetness of honey sage syrup, creating a drink that feels warm and inviting.

The touch of citrus from an orange twist brightens the flavors, adding balance to the rich, earthy notes. Each sip is smooth, slightly sweet, and perfectly spiced, making it an ideal choice for cold winter nights. Whether served at a holiday gathering or enjoyed by the fire, this cocktail adds a touch of elegance to any evening.

The Bourbon Coconut Milk is a cozy and creamy cocktail that’s perfect for warming up on a cold winter evening. It blends the smooth flavor of bourbon with the rich combination of whole milk and coconut milk, creating a silky texture that feels both comforting and indulgent.

A touch of brown sugar adds gentle sweetness, while freshly grated nutmeg on top gives it a festive aroma and flavor. Each sip is warm, soothing, and perfectly balanced. Whether you’re relaxing by the fire or hosting a holiday gathering, this drink is an inviting way to enjoy the season’s comforting flavors.

The Bourbon Chai Tea is a warm and soothing drink that combines the bold flavor of black tea with the comforting taste of winter spices. Blended with almond milk, a splash of bourbon, and a touch of vanilla, it offers the perfect mix of richness and warmth.

The honey adds gentle sweetness, balancing the earthy and spicy notes of the chai. Each sip feels smooth, aromatic, and deeply comforting, making it an ideal drink for cold nights or festive gatherings. Whether enjoyed alone or shared with friends, this Bourbon Chai Tea is a cozy way to unwind and savor the season.

The Spiced Cranberry Bourbon Cocktail is a festive and comforting drink that captures the warmth of the holiday season. It combines the smooth richness of bourbon with spiced cranberry juice for a balance of sweetness and tartness.

A splash of ginger beer adds a lively sparkle, making the drink both refreshing and flavorful. The finishing touch of freshly grated nutmeg adds a cozy aroma and a hint of spice that ties everything together. Perfect for winter parties or quiet evenings by the fire, this cocktail brings a touch of cheer and sophistication to any holiday celebration or chilly night.

The Winter Spice Old Fashioned is a rich and flavorful twist on the classic cocktail, perfect for cold nights and festive gatherings. It blends the deep, smooth taste of bourbon with the bittersweet flavor of Cynar and the warmth of a spiced simple syrup.

The result is a drink that feels both bold and comforting, with hints of cinnamon, clove, and ginger that bring to mind freshly baked gingerbread. A star anise garnish adds a fragrant finish and an elegant touch. Perfect for sipping by the fire, this cocktail captures the cozy, aromatic essence of the winter season.

The Boulevardier is a classic winter cocktail that brings warmth and elegance to any festive gathering. Made with whiskey, sweet vermouth, and Campari, it strikes a perfect balance of rich, smooth, and slightly bitter flavors.

The whiskey adds depth and warmth, while the vermouth brings sweetness and the Campari adds a hint of citrus and spice. Simple to prepare in just a few minutes, it can be served in a chilled cocktail glass or poured over ice for a more relaxed feel. Whether for a cozy evening or a holiday celebration, the Boulevardier is timeless, bold, and effortlessly sophisticated.

The Santa Claus Smash is a cheerful holiday cocktail that brings together bright fruit flavors and the warming depth of bourbon. Fresh pomegranate juice adds a tart, juicy quality that balances beautifully with the smooth, rich notes of the whiskey.

A touch of ginger brings gentle spice, while a splash of ginger beer on top adds sparkle and a refreshing finish. Garnished with mint and pomegranate arils, the drink looks festive and colorful, making it just right for holiday parties. At the same time, its cozy mix of flavors makes it a perfect choice for quiet winter evenings at home.

The Cherry Bourbon Chocolate is a comforting winter cocktail that combines the richness of hot chocolate with the bold flavor of cherry bourbon. The smooth chocolate base brings a deep, sweet taste, while the bourbon adds warmth and a touch of fruitiness that makes each sip feel special.

Topped with a layer of whipped cream, this drink feels cozy and inviting, perfect for enjoying on a cold evening by the fire. Finished with a garnish that adds both color and charm, it is an ideal choice for winter celebrations or simply treating yourself to something warm and satisfying.

Bad Santa is a holiday cocktail that gives classic eggnog a stronger, more spirited twist. The creamy texture of traditional eggnog sets the base, while bourbon adds warmth and a bold kick that makes the drink stand out. The balance of sweetness and spice creates a comforting flavor that feels perfect for winter gatherings.

A dusting of freshly grated nutmeg brings a fragrant holiday touch, and a cinnamon stick garnish adds both aroma and charm. This drink is ideal for anyone who enjoys their seasonal cocktails rich, flavorful, and with just the right amount of strength to keep the mood festive.

The Tipsy Elf is a festive spin on the timeless Boulevardier, crafted to bring warmth and cheer to the holiday season. At its heart is smooth bourbon, which provides depth and richness, paired with sweet vermouth that adds a layer of gentle sweetness. Campari contributes a bold, bittersweet edge that ties the drink together, giving it both strength and balance.

An orange garnish adds brightness and a touch of citrus aroma that rounds out the flavors beautifully. With its classic base and seasonal character, this cocktail is a great choice for holiday parties or relaxing evenings by the fire.

The Persimmon Old Fashioned is a holiday cocktail that brings a cozy mix of flavors while keeping the classic character of an Old Fashioned. Bourbon forms the base, offering warmth and richness, while homemade persimmon syrup adds a gentle sweetness with a seasonal touch.

Orange bitters provide a hint of citrus and spice that balances the drink, keeping it both bold and smooth. A fresh persimmon slice and a star anise garnish make the presentation festive and inviting. This cocktail feels special yet familiar, making it an excellent choice for holiday parties or quiet evenings at home.

Cranberry Bourbon Punch is a holiday cocktail that brings together bright fruit flavors with the smooth depth of bourbon. The bold character of the whiskey is softened by the sweetness of vermouth and balanced with the crisp taste of cranberry juice.

A splash of orange juice adds freshness, while a touch of simple syrup ties everything together with gentle sweetness. The drink is finished with a garnish of rosemary, fresh cranberries, and a slice of orange, giving it both color and aroma. Festive, flavorful, and easy to share, this punch is perfect for gatherings and holiday celebrations.

The Pumpkin Pie Whiskey Sour is a seasonal twist on the classic sour, blending the bold warmth of bourbon with the cozy flavors of pumpkin spice. Fresh lemon juice brightens the drink, while pumpkin spice syrup provides sweetness and autumn character.

The addition of egg white gives the cocktail a smooth, frothy texture that makes each sip feel rich and satisfying. Finished with aromatic Peychaud’s bitters and a light dusting of nutmeg, this cocktail is both comforting and balanced a festive way to enjoy whiskey with a fall-inspired flair.

The Bourbon Pear Fizz is a seasonal cocktail that combines rich warmth with light, refreshing sparkle. At its base is smooth bourbon, which gives the drink depth and a touch of strength. Spiced pear syrup adds gentle sweetness with a hint of seasonal spice, making the flavor feel cozy and inviting.

A splash of Prosecco brings bubbles and brightness, turning the drink into something festive and lively. Garnished with a pear slice or a sprig of herbs, it looks as good as it tastes. This cocktail is a wonderful choice for fall and winter gatherings, from parties to quiet evenings.

The Hot Toddy is a classic warm cocktail that has been enjoyed for generations during the colder months. Known for its soothing qualities, it blends whiskey with hot water, honey, and lemon to create a drink that is both comforting and flavorful. The whiskey provides warmth and depth, while honey adds gentle sweetness and lemon brings brightness and balance.

Often finished with a cinnamon stick or clove garnish, the aroma adds an extra touch of coziness. Perfect for cold winter nights or when you need something soothing, the Hot Toddy is a timeless favorite for seasonal gatherings and quiet evenings.