17 Winter Bourbon Cocktails to Try This Season

Winter is bourbon’s time to shine. Its rich caramel, oak, and vanilla notes create the perfect base for cozy, full-bodied cocktails that warm you from the inside out. Whether you love classic Old Fashioneds, creamy dessert-style drinks, or bold modern creations, bourbon can do it all — from fireside sipping to festive gatherings.

These 17 bold winter bourbon cocktails are designed to showcase the spirit’s depth while embracing the season’s best flavors — maple, apple, cinnamon, chocolate, and more.

Get ready to pour, stir, and savor bourbon’s warmth in every glass.

1. Maple Cinnamon Bourbon Old Fashioned

This comforting twist on the classic Old Fashioned infuses bourbon with sweet maple syrup and a touch of cinnamon. It’s smooth, rich, and perfectly balanced — ideal for slow sipping on cold evenings.

Ingredients:

1. 2 oz bourbon
2. ½ oz maple syrup
3. 2 dashes Angostura bitters
4. Pinch of ground cinnamon
5. Orange peel for garnish

Steps:

1. Stir bourbon, maple syrup, bitters, and cinnamon with ice in a mixing glass.
2. Strain into a rocks glass over a large ice cube.
3. Garnish with a twist of orange peel.

2. Spiced Apple Bourbon Smash

Sweet apple, zesty lemon, and warm cinnamon make this cocktail taste like a cozy slice of apple pie. The bourbon adds depth and spice, making it perfect for crisp winter nights.

Ingredients:

1. 2 oz bourbon
2. ½ oz lemon juice
3. ½ oz honey syrup
4. ¼ cup apple slices
5. Pinch of cinnamon

Steps:

1. Muddle apple slices and honey syrup in a shaker.
2. Add bourbon, lemon juice, and cinnamon with ice.
3. Shake well and strain into a glass with fresh ice.
4. Garnish with an apple slice or cinnamon stick.

3. Brown Sugar Bourbon Hot Toddy

A rich and velvety upgrade to the traditional hot toddy, this version uses brown sugar and a squeeze of lemon for a beautifully balanced sweet-tart drink. It’s soothing, aromatic, and perfect for chilly evenings.

Ingredients:

1. 2 oz bourbon
2. 1 tbsp brown sugar
3. ½ oz lemon juice
4. Hot water (to fill)
5. Cinnamon stick for garnish

Steps:

1. Add brown sugar and lemon juice to a mug.
2. Pour in hot water and stir until the sugar dissolves.
3. Add bourbon and stir again.
4. Garnish with a cinnamon stick.

4. Bourbon Buttered Pecan

This indulgent cocktail tastes like a liquid dessert — nutty, buttery, and beautifully smooth. It’s a decadent treat that pairs perfectly with winter desserts or cozy nights in.

Ingredients:

1. 2 oz bourbon
2. 1 oz pecan syrup or praline liqueur
3. ½ oz cream
4. Dash of vanilla extract

Steps:

1. Combine all ingredients in a shaker with ice.
2. Shake until frothy and chilled.
3. Strain into a rocks glass and garnish with crushed pecans.

5. Smoked Orange Bourbon Sour

A smoky twist on the classic sour, this cocktail combines bourbon’s caramel depth with charred orange and lemon for a bold, aromatic finish. It’s both bright and brooding — a true winter standout.

Ingredients:

1. 2 oz bourbon
2. ¾ oz lemon juice
3. ½ oz smoked orange syrup or orange juice
4. ½ oz simple syrup
5. Ice cubes

Steps:

1. Add all ingredients to a shaker with ice.
2. Shake vigorously until well chilled.
3. Strain into a glass over ice and garnish with a flamed orange peel.

6. Chocolate Bourbon Manhattan

This elegant winter twist on the Manhattan adds a splash of chocolate liqueur for a silky richness that enhances bourbon’s natural sweetness. It’s refined, indulgent, and perfect for after-dinner sipping.

Ingredients:

1. 2 oz bourbon
2. ½ oz chocolate liqueur
3. ½ oz sweet vermouth
4. 2 dashes chocolate or aromatic bitters
5. Cherry for garnish

Steps:

1. Stir all ingredients with ice in a mixing glass.
2. Strain into a chilled coupe or martini glass.
3. Garnish with a cherry.

7. Ginger Maple Bourbon Mule

This cozy mule variation brings together spicy ginger beer, earthy maple syrup, and rich bourbon for a winter-friendly refreshment. It’s bubbly, aromatic, and perfectly balanced with a hint of sweetness.

Ingredients:

1. 2 oz bourbon
2. ½ oz maple syrup
3. ½ oz lime juice
4. Ginger beer (to top)
5. Lime wedge and candied ginger for garnish

Steps:

1. Add bourbon, maple syrup, and lime juice to a copper mug filled with ice.
2. Stir and top with ginger beer.
3. Garnish with a lime wedge and piece of candied ginger.

8. Bourbon Chai Latte

Warm, creamy, and spiced just right, this drink blends bourbon with chai tea and honey for a comfort-in-a-cup experience. It’s sweet, aromatic, and perfect for unwinding on a cold day.

Ingredients:

1. 1½ oz bourbon
2. 3 oz brewed chai tea (hot)
3. ½ oz honey syrup
4. 1 oz milk or cream
5. Ground cinnamon for garnish

Steps:

1. Combine bourbon, chai tea, honey syrup, and milk in a mug.
2. Stir until smooth and well blended.
3. Sprinkle cinnamon on top before serving.

9. Caramel Bourbon Eggnog

Nothing says winter comfort like eggnog — especially when paired with smooth, caramel-kissed bourbon. This creamy cocktail is festive, indulgent, and a must-have for any holiday celebration.

Ingredients:

1. 2 oz bourbon
2. 4 oz eggnog
3. ½ oz caramel syrup
4. Ground nutmeg for garnish

Steps:

1. Shake bourbon, eggnog, and caramel syrup with ice until frothy.
2. Strain into a glass.
3. Dust with nutmeg before serving.

10. Bourbon Cranberry Smash

This cocktail delivers the perfect mix of tart cranberries and deep bourbon warmth. The vibrant red hue makes it an ideal choice for holiday parties or cozy evenings at home.

Ingredients:

1. 2 oz bourbon
2. ½ oz lemon juice
3. ½ oz simple syrup
4. ¼ cup fresh cranberries
5. Club soda (to top)

Steps:

1. Muddle cranberries and syrup in a shaker.
2. Add bourbon, lemon juice, and ice. Shake well.
3. Strain into a glass and top with club soda.
4. Garnish with a rosemary sprig.

11. Vanilla Orange Bourbon Spritz

A light yet warming cocktail that balances bourbon’s depth with citrusy freshness. The touch of vanilla brings a soft, sweet finish that makes every sip feel festive and bright.

Ingredients:

1. 2 oz bourbon
2. 1 oz orange juice
3. ½ oz vanilla syrup
4. Sparkling water (to top)
5. Orange slice for garnish

Steps:

1. Add bourbon, orange juice, and vanilla syrup to a shaker with ice.
2. Shake lightly and strain into a glass with ice.
3. Top with sparkling water and garnish with an orange slice.

12. Bourbon Hot Chocolate

Rich, velvety, and irresistibly cozy, this drink blends creamy hot chocolate with smooth bourbon for the ultimate winter comfort. It’s a luxurious treat for snow days or nights by the fire.

Ingredients:

1. 1½ oz bourbon
2. 1 cup milk
3. 2 tbsp cocoa powder
4. 1 tbsp sugar
5. Whipped cream and chocolate shavings for garnish

Steps:

1. Warm milk, cocoa powder, and sugar in a saucepan until smooth.
2. Remove from heat and stir in bourbon.
3. Pour into a mug and top with whipped cream and chocolate shavings.

13. Smoked Maple Bourbon Flip

Creamy, frothy, and slightly smoky, this cocktail feels indulgent yet balanced. The maple and bourbon pair beautifully with the velvety texture from the egg — a sophisticated winter sipper.

Ingredients:

1. 2 oz bourbon
2. ½ oz maple syrup
3. 1 whole egg
4. Dash of smoked salt or bitters

Steps:

1. Add all ingredients to a shaker without ice and shake vigorously.
2. Add ice and shake again until well chilled.
3. Strain into a coupe glass and sprinkle a bit of smoked salt on top.

14. Cherry Vanilla Bourbon Smash

This rich and fruity cocktail layers deep cherry flavors with bourbon’s caramel smoothness. The hint of vanilla ties everything together, making it both elegant and comforting.

Ingredients:

1. 2 oz bourbon
2. ½ oz vanilla syrup
3. ½ oz lemon juice
4. ¼ cup pitted cherries (fresh or frozen)

Steps:

1. Muddle cherries and syrup in a shaker.
2. Add bourbon, lemon juice, and ice.
3. Shake well and strain into a glass with ice.
4. Garnish with a cherry.

15. Cinnamon Bourbon Cider

Warm, spiced, and perfectly seasonal — this cocktail is fall and winter in a glass. It’s simple to make but full of cozy, layered flavor that instantly sets the mood.

Ingredients:

1. 2 oz bourbon
2. 4 oz warm apple cider
3. ¼ tsp ground cinnamon
4. Apple slice for garnish

Steps:

1. Warm the cider in a saucepan with cinnamon.
2. Pour into a mug and add bourbon.
3. Stir gently and garnish with an apple slice.

16. Espresso Maple Bourbon Martini

A sophisticated winter cocktail for coffee lovers, this martini blends bold espresso with bourbon and maple for a rich, warming kick. It’s smooth, aromatic, and slightly sweet—an instant classic.

Ingredients:

1. 1½ oz bourbon
2. 1 oz espresso (cooled)
3. ½ oz maple syrup
4. ¼ oz coffee liqueur

Steps:

1. Shake all ingredients with ice until well-chilled.
2. Strain into a martini glass.
3. Garnish with coffee beans.

17. Winter Bourbon Punch

This crowd-pleasing punch combines citrus, cranberry, and spiced bourbon flavors for a bright yet warming holiday drink. It’s easy to make in batches and perfect for winter celebrations.

Ingredients:

1. 1 cup bourbon
2. 2 cups cranberry juice
3. 1 cup orange juice
4. ½ cup lemon juice
5. Sparkling water (to top)
6. Orange slices and cranberries for garnish

Steps:

1. Combine all juices and bourbon in a large pitcher.
2. Chill for 30 minutes before serving.
3. Pour into glasses over ice, top with sparkling water, and garnish with fruit.