Cranberry Cinnamon Whiskey Sour

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Fall just isn’t fall without cranberries and cinnamon, and this Cranberry Cinnamon Whiskey Sour wraps them both up in one smooth, seasonal sip. It’s tart from the cranberries, warm with spice, and mellowed by a touch of vanilla—basically autumn in a glass. If a classic whiskey sour is your go-to, this cozy twist will be your new favorite fall cocktail.

When it comes to spirits, whiskey is hands down my favorite. Neat, it’s rich and complex; in a cocktail, it brings a bold, smoky backbone you can’t miss. If whiskey hasn’t won you over yet, this Cranberry Cinnamon Whiskey Sour might just change your mind. And if you’re already a sour lover, don’t miss my Spiced Pomegranate Rum Sour, another fall favorite that’s perfect for sharing with guests.

Which Whiskey is best for a fall Whiskey Sour?

While I could wax poetic about brands, styles, and aging, my rule of thumb for mixing whiskey is simple: save the pricey bottles for sipping neat. For cocktails, reach for something you enjoy but won’t mourn losing to citrus and spice. A solid, budget-friendly option like Bulleit Rye or Jim Beam Bourbon will do the trick beautifully.

What is a Sour?

A sour is a simple formula—spirit, citrus, and sweetener—and the whiskey sour is one of the best-known examples. This Cranberry Cinnamon Whiskey Sour follows that classic structure but with a distinctly autumn twist. Picture a New England hillside in peak color, cranberry bogs nearby, and warm cinnamon drifting from the kitchen—that’s the flavor story in your glass.

While this fall Whiskey cocktail only requires 4 ingredients, there is one ingredient you need that I recommend you make from scratch: cinnamon vanilla syrup. It is wonderfully easy to make and tastes so much better than commercial syrup with preservatives or artificial flavors. Plus you can make a big batch and store it in the fridge for many more cocktails.

The cranberry juice is also an important ingredient. To get the most out of this flavor it needs to be pure cranberry (not cranberry juice cocktail) and ideally unsweetened.

Ingredients Notes:

This fall whiskey cocktail may only call for four ingredients, but one of them is worth making from scratch: cinnamon vanilla syrup. It’s incredibly simple, tastes worlds better than anything with preservatives or artificial flavoring, and a batch will keep in the fridge for plenty more cocktails.

The cranberry juice matters too—skip the cranberry cocktail blends and go for pure, unsweetened cranberry juice to really let that tart, bold flavor shine.

Tools you will need:

• Boston Shaker or Cobbler Shaker. I highly recommend the Yeti Rambler. If you know Yeti products you know this is high-quality. It’s great for making 1-2 cocktails at a time and has a phenomenal seal (a lot of cobbler shakers tend to leak).
• Measuring Jigger
• Cocktail Strainer. You don’t need this if using a cobbler shaker like the Yeti Rambler.
• Your favorite double old-fashioned or rocks glass. The smoked Buchanan glass from CB2 is one of my favorites and I love that you can stack them for easy storage.

How to make a Cranberry Cinnamon Whiskey Sour:

1. Add the whiskey, cranberry juice, lemon juice and cinnamon vanilla simple syrup to your mixing glass.
2. Fill with ice and shake vigorously.
3. Strain over fresh ice in your glass.
4. Garnish with cinnamon.

How to make the Cinnamon Vanilla Syrup:

Ingredients:

• 1 cup water
• 1 cup sugar
• 1 tsp vanilla extract
• 4-6 cinnamon sticks

Instructions:

1. Add the water and sugar to a small saucepan. Bring the water to a boil and stir until the sugar is completely dissolved.
2. Add 4-6 cinnamon sticks. Reduce the heat and simmer for about 10 minutes.
3. Remove from heat then cover with a lid and let sit for a minimum of one hour before you use it. The longer you let it sit the more flavor you will get from the cinnamon.
4. Next, add the vanilla extract and stir to combine.
5. Transfer to a syrup bottle with a tight seal.
6. Store in the refrigerator for up to 2 weeks.

Notes:  

• You can remove the cinnamon sticks if you want, but I prefer to leave them in so they continue to marinade and add more cinnamon flavor.
• The quality of vanilla extract you use will make a difference in flavor. Use the best quality you can find.

Can I substitute the Cranberry Juice?

Need a cocktail in a hurry but out of cranberry juice? No problem—there are a few swaps that still make a fantastic fall whiskey sour. Just keep in mind the flavor will shift from my original recipe (in a good way). Here are some solid options:

• Pomegranate Juice – Naturally sweeter, so cut the syrup in half.
• Cherry Juice – Tart cherry works beautifully; if you only have a sweeter version, dial back the syrup.
• Apple Juice – A fall classic, but definitely sweet—halve the syrup to keep it balanced.

Whether you’re cozying up by the fire or hosting friends who love a little warmth in their sip, this Cranberry Cinnamon Whiskey Sour hits all the fall notes—tart, sweet, spicy, and perfectly balanced. If you want to wander further down bourbon’s tree-lined path, I’ve got more cocktails where this came from. Try my Apple Cinnamon Bourbon Sour for a crisp apple twist, or embrace deep sweetness with the Maple Boston Sour if you’re feeling extra decadent.

Cheers to rich flavors and memorable sips!

♥ Jessica

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