Why You’ll Love This Recipe

I’m a loyalist when it comes to the classic old-fashioned, but every November I want something that tastes a little more like the season. Swapping the sugar cube for a homemade cranberry-orange syrup does exactly that. It adds a gentle tartness, a rosy blush, and a bright citrus note that plays beautifully with the caramel and vanilla in good bourbon. The drink is still strong, smooth, and simple, but it tastes like a holiday table. The syrup keeps for two weeks, so each cocktail takes about two minutes to stir together, and a flamed orange peel on top makes it feel like a bar-quality drink at home.

Ingredients

For the cranberry-orange syrup (makes about 1 cup)

1 cup fresh or frozen cranberries
3/4 cup sugar
3/4 cup water
3 strips orange peel (pith removed)
1 cinnamon stick
1 tablespoon fresh orange juice

For the cocktail (makes 1)

2 oz bourbon or rye whiskey
1/2 oz cranberry-orange syrup, plus more to taste
2 dashes Angostura bitters
1 dash orange bitters
Ice (one large cube for serving, plus regular ice for stirring)

For garnish

1 wide strip orange peel
3 fresh or sugared cranberries
Brandied or Luxardo cherry (optional)

Directions

Make the syrup. In a small saucepan, combine the cranberries, sugar, water, orange peel, and cinnamon stick. Bring to a boil, then reduce the heat and simmer for 10 minutes, until the berries burst and the liquid turns deep red.
Strain. Remove from the heat, stir in the orange juice, and let steep for 15 minutes. Strain through a fine-mesh sieve, pressing gently on the solids. Cool completely.
Chill the glass. Place a rocks glass in the freezer for 10 minutes, or fill it with ice water while you mix.
Combine. Add the bourbon, 1/2 ounce of syrup, Angostura bitters, and orange bitters to a mixing glass.
Stir. Fill the mixing glass with ice and stir for 25 to 30 seconds, until very cold and slightly diluted.
Strain. Place the large ice cube in the chilled rocks glass and strain the cocktail over it.
Express the orange peel. Hold the peel skin-side down about 3 inches above the drink and pinch it to release the oils. For a flamed peel, hold a lit match between the peel and the drink, then squeeze so the oils spark over the surface. Rub the peel around the rim and drop it in.
Garnish. Add the cranberries and a cherry, if using, and serve right away.

Servings and Timing

Servings: 1 cocktail (the syrup makes about 12 drinks)
Prep time: 5 minutes for the drink, plus 10 minutes for the syrup
Cook time: 10 minutes (syrup only)
Total time: About 30 minutes including cooling, or 2 minutes once the syrup is made

Batch version (serves 8): Combine 2 cups bourbon, 4 ounces syrup, 16 dashes Angostura, and 8 dashes orange bitters in a bottle with 3 ounces of water. Chill, then pour over ice and garnish each glass.

Variations

Spiced: Add a star anise pod or 3 whole cloves to the syrup.
Maple: Replace half the syrup with pure maple syrup for a deeper, woodsier sweetness.
Smoky: Rinse the glass with a splash of mezcal or peated Scotch before pouring.
Rye or aged rum: Use rye for a spicier edge or aged rum for a rounder, sweeter profile.
Cranberry Manhattan: Swap the syrup for 1/2 ounce cranberry juice and add 1/2 ounce sweet vermouth.
Low-proof: Use 1 oz bourbon and 1 oz amaro or sweet vermouth.
Mocktail: Combine 2 oz strong black tea, 1/2 oz syrup, 2 dashes bitters, and a splash of orange juice. Stir over ice.
Sugar-free: Make the syrup with a 1:1 sugar substitute and reduce simmer time slightly.

Storage and Reheating

Cocktail: Best served immediately, since dilution continues as the ice melts.
Syrup: Store in a sealed jar in the refrigerator for up to 2 weeks. Add 1 ounce of vodka to stretch it to a month.
Batched cocktail: Without ice, keep in a sealed bottle in the fridge for up to 2 days, or in the freezer for up to 1 week.
Garnishes: Cut orange peels a few hours ahead and cover to keep them from drying out.
Reheating: Not applicable. This is served cold.

FAQs

What’s the best bourbon for an old-fashioned?
A mid-priced bourbon around 90 to 100 proof is ideal. Look for something with caramel and vanilla notes, such as Buffalo Trace, Maker’s Mark, or Wild Turkey 101.

Why a large ice cube?
A big cube melts slowly, so the drink stays cold without becoming watery. Silicone molds make 2-inch cubes easily.

Do I need two kinds of bitters?
Angostura is the classic backbone, and orange bitters brighten the citrus. If you only have one, Angostura on its own works fine.

Is the flamed peel necessary?
No. It adds a toasty, caramelized orange aroma, but a simple expressed peel is still lovely.

Can I use cranberry juice instead of syrup?
You can, but the drink will be thinner and tarter. Use 1/2 ounce of juice plus 1/4 ounce simple syrup.

Why should an old-fashioned be stirred, not shaken?
Stirring chills and dilutes the drink while keeping it clear and silky. Shaking adds air and cloudiness.

How strong is it?
It’s a spirit-forward drink, with about 2 ounces of bourbon, or roughly one and a half standard drinks. Sip slowly, and offer the mocktail version to guests who aren’t drinking.

Conclusion

This cranberry-orange old-fashioned is my go-to cocktail from Thanksgiving through New Year’s. It’s smooth, warming, and gently tart, with a bright orange aroma in every sip. I hope it becomes a ritual at your holiday gatherings, too. If you make it, I’d love to hear how you garnished yours!

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This Cranberry-Orange Old-Fashioned puts a festive spin on the classic whiskey cocktail with a homemade cranberry-orange syrup, aromatic bitters, and a flamed orange peel. Bourbon’s caramel and vanilla notes pair beautifully with tart cranberry and bright citrus. It’s a sophisticated, sip-worthy drink for the holidays that comes together in minutes once the syrup is made.

Author: Laura
Prep Time: 5 minutes (plus 25 minutes for the syrup)
Cook Time: 10 minutes
Total Time: 30 minutes
Yield: 1 cocktail
Category: Drinks
Method: Stirring
Cuisine: American

Instructions

Make the syrup: Combine the cranberries, water, sugar, orange peel, and cinnamon stick in a small saucepan. Bring to a boil, stirring until the sugar dissolves.
Simmer: Reduce the heat and simmer for 10 minutes until the cranberries burst.
Strain and cool: Strain through a fine-mesh sieve, pressing gently on the berries. Cool completely and store in the fridge.
Build the drink: In a rocks glass, combine the bourbon, 1/2 ounce of cranberry-orange syrup, Angostura bitters, and orange bitters.
Add ice: Add a large ice cube and stir for 20-30 seconds until well chilled.
Express the peel: Hold the orange peel skin-side down over the glass and squeeze to release the oils. For flair, flame it briefly with a lit match, then rub the peel around the rim.
Garnish: Drop the peel into the drink and add the cranberries and a cinnamon stick.
Serve: Serve immediately.

Notes

The syrup makes about 1 1/4 cups, enough for 8-10 cocktails. It keeps in the fridge for up to 2 weeks.
Use a large ice cube so the drink stays cold without diluting too quickly.
Bourbon gives a sweeter, rounder flavor, while rye adds a spicy, drier edge.
Use unsweetened cranberries for the syrup and adjust the sugar if you like a tarter drink.
Batch for a party: mix 16 oz whiskey, 4 oz syrup, 16 dashes Angostura, and 8 dashes orange bitters in a bottle, add 3 oz water, and chill. Pour over ice to serve.
Please drink responsibly.

Nutrition

Serving Size: 1 cocktail
Calories: 185
Sugar: 9 g
Sodium: 2 mg
Fat: 0 g
Saturated Fat: 0 g
Unsaturated Fat: 0 g
Trans Fat: 0 g
Carbohydrates: 10 g
Fiber: 0 g
Protein: 0 g
Cholesterol: 0 mg