Name: Cinnamon Old Fashioned
Prep time: 3 min
Total time: 3 min
Yield: 1
Ingredients: 2 oz bourbon; 1/4 oz cinnamon simple syrup (see recipe above or buy it); 3 dashes chocolate bitters; Garnish: Cinnamon stick

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The Cinnamon Old Fashioned is a warm, inviting twist on the original Old Fashioned that’s just right for enjoying in the autumn.

Why You Should Try the Cinnamon Old Fashioned

If you’re a fan of the classic Old Fashioned, the Cinnamon Old Fashioned is a must-try. It takes everything you love about the original and adds a touch of seasonal flair that’s perfect for the cooler months.

But beyond that, this really is a fantastic cocktail in its own right. The cinnamon simple syrup adds a unique depth of flavor that complements the bourbon beautifully, while the chocolate bitters provide a subtle complexity that keeps you coming back for more.

The warm, cozy flavors make it the perfect cocktail to sip on a chilly evening, whether you’re curled up by the fireplace or hosting a cozy gathering with friends.

Tasting Notes

The first sip of this Cinnamon Old Fashioned reveals rich, oaky notes of the bourbon balanced by the sweet, aromatic cinnamon simple syrup. The chocolate bitters add a subtle depth of flavor that ties everything together beautifully.

As you sip, you’ll notice the cinnamon aroma wafting up. And then the finish is where the real magic happens. The cinnamon lingers pleasantly, leaving you with a warm, comforting sensation that just begs you to take another sip.

It’s the kind of cocktail that you could sip slowly and savor, letting the flavors unfold with each passing moment.

How to Make Cinnamon Simple Syrup (and Store It)

The cinnamon simple syrup is the heart of this cocktail. It’s super easy to make at home and keeps well.

Basic ratio: Combine 1 cup sugar and 1 cup water in a small saucepan. Add 2–3 cinnamon sticks (or 1–2 teaspoons ground cinnamon, though sticks give a cleaner flavor).
Heat: Warm over medium heat just until the sugar dissolves. Don’t let it boil long; a gentle simmer for a minute is enough.
Steep: Remove from heat and let the mixture cool and steep for 15–30 minutes for a milder flavor, or up to a few hours for stronger cinnamon notes.
Strain: Strain out the cinnamon sticks (or use a fine mesh to catch grounds).
Storage: Put the syrup in a clean bottle in the fridge. It will keep for about 2–3 weeks. Label with the date so no one’s guessing later.
Tip: For a spiced syrup, add star anise, a clove, or a small piece of vanilla bean while heating. Just remember those flavors will be present, so don’t overdo it.

Overhead view of Cinnamon Old Fashioned cocktail

Picking the Right Bourbon

Bourbon choice matters here because cinnamon syrup emphasizes the spirit’s sweeter, oakier traits. Mid-shelf bourbons with vanilla, caramel, and light spice notes work best. Think of bourbons where the sweetness can meet the cinnamon without being lost.

Avoid overly sweet or flavored whiskeys: Extremely sweet or heavily finished bourbons can make the drink cloying. You may be tempted to use a cinnamon flavored whiskey, but it will lose some of the essential bourbon flavor.

No need to splurge on ultra-premium bottles. A good-quality bottle in the $30–$60 range will make an excellent Cinnamon Old Fashioned.

Glassware and Ice Tips

Small details help make the drink feel special and improve each sip. A classic rocks glass (old-fashioned glass) is perfect. It’s sturdy, lets aromas gather, and looks right for a slow-sip cocktail.

For ice, use one large ice cube or a large sphere if possible. Large ice melts more slowly, chilling the drink while preserving flavor without watering it down quickly.

You can never go wrong pre-chill the glasses in the freezer for a few minutes. It makes the drink feel crisper right away.

Presentation and Garnish Ideas

A good garnish isn’t just decoration. It adds aroma and rounds out the flavor.

The classic cinnamon stick garnish gives aroma and looks cozy. Light it briefly with a match to release more scent if you want a smoky warmth (don’t leave it burning).

A thin orange peel expressed over the glass adds bright citrus oils that cut through richness. Or you could add an element of chocolate by shaving a little dark chocolate over the top. Or use chocolate bitters with a chocolate-topped orange twist.

Serving Occasions

This cocktail fits a lot of settings. It’s not just for dessert time. It’s great for quiet evenings at home, especially when it’s chilly.

But you can also serve it after a hearty meal as an after-dinner sipper with dessert or cheese. And since cinnamon signals holiday flavors, it works great for Thanksgiving, Christmas, or seasonal parties.

It’s a surprisingly good porch or firepit cocktail. It gets you warm without being heavy.

Food Pairings

Try serving the Cinnamon Old Fashioned alongside a rich, decadent dessert like a warm apple pie or a chocolate lava cake. The cinnamon and chocolate notes in the cocktail will complement the sweetness of the dessert beautifully.

If you’re in the mood for something a little more savory, this drink also pairs wonderfully with grilled meats, especially those with a hint of spice or sweetness. Think a juicy steak with a cinnamon-sugar rub, or a rack of barbecue ribs glazed with a cinnamon-infused sauce.

A rich, creamy cheese plate works perfectly, too. The contrast of the bold, spicy-sweet cocktail and the creamy, savory cheeses is simply divine.