10 of the Best Bourbon Cocktails for Fall

All September on VinePair, we’re turning our focus to America’s spirit: bourbon. For our third annual Bourbon Month, we’re exploring the industry legends and innovators, our favorite craft distilleries, new bottles we love, and more.

The buzz surrounding fall drinks is almost as inevitable as the leaves changing colors (we’re looking at you, PSL), and there are few drinks more quintessentially autumn than bourbon. If the color alone — ranging from light amber to deep mahogany — isn’t enough to make you dream of crunchy leaves and crisp temperatures, the notes of vanilla, oak, nutmeg, and caramel will surely get you in the autumnal mood.

Looking to add a little more bourbon into your fall cocktail lineup? Read on for the perfect cocktail recipes that marry the iconic American drink and some of the season’s favorite flavors.

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OLD FASHIONED

The Old Fashioned recipe

This classic cocktail is one of the oldest and most popular of all time. You don’t have to have a loaded bar cart to make this one, either. Just combine bourbon, simple syrup, and bitters in a rocks glass. Make sure to stir and add ice, then garnish with a lemon and orange twist for a drink filled with rich, spiced flavors.

BOURBON APPLE CIDER SOUR

The Bourbon Apple Cider Sour recipe

Apple cider fans, fall was made for you. The cooler months are the perfect time to enjoy apples in their prime. Pour your favorite cider into a cocktail shaker, then add bourbon, lemon juice, egg white, and cinnamon. Give it a good dry shake, add ice, then repeat. Strain into a serving glass of your choice, and make sure to garnish with some fresh apple slices and cinnamon.

THE BOURBON OREO MILKSHAKE

The Bourbon Oreo Milkshake recipe

Halloween sweets aren’t just for kids. Throw your favorite bourbon, vanilla ice cream, and Oreo cookies into a blender, then fill a glass of your choice to the brim with the frothy, boozy mix. Garnish with an Oreo if you haven’t already eaten the rest.

THE SMOKE, SPICE, AND EVERYTHING NICE

The Smoke, Spice, and Everything Nice recipe

As its name suggests, this smoky, aromatic drink channels nights spent around a firepit. To make one, you’ll need bourbon, rye, mezcal, strawberry syrup, and aromatic bitters. Stir them together in a cocktail glass with ice, then strain into a cocktail glass for the perfect blend of a Manhattan and a De La Louisiane.

THE BUTTERED PECAN OLD FASHIONED

The Butter Pecan Old Fashioned recipe

If you can’t wait until November for a slice of pecan pie, you can come close with this take on the Old Fashioned. Buttered pecan simple syrup steals the show in this cocktail. Add it, along with bourbon and aromatic bitters, to a mixing glass with ice, then stir and strain into a rocks glass with an ice cube. Sip for sweet, buttery bliss.

BOULEVARDIER

The Boulevardier recipe

The Boulevardier draws much of its inspiration from the Negroni, but nixes the gin in favor of bourbon. Combine Campari, sweet vermouth, and (you guessed it) bourbon into a glass with ice. Stir and strain into a chilled rocks glass with fresh ice, and top it off with an orange twist.

THE NOR’EASTER

The Nor'easter recipe

This drink is the perfect storm of autumn flavors. The Nor’easter, a festive creation dreamed up by two New York City bartenders, combines apple brandy, maple syrup, and bourbon for the perfect combination of sweetness and spice. Flavors abound with added egg white, dried poblano chiles, lemon juice, and lime juice. Shake until foamy, then serve in a coupe glass with a pinch of cinnamon to garnish.

THE BANKER’S CHOICE

The Banker's Choice recipe

Coffee cocktails go way beyond the Espresso Martini. Made with coffee-infused bourbon, the Banker’s Choice evokes notes of smooth chocolate, caramel, and ripe orange. Steep bourbon and coffee beans for three hours, then mix with maple syrup, Lazzaroni Amaro, and crème de pêche. The result is an elegant sipper that’s best served neat.

WALNUT AND MAPLE OLD FASHIONED

The Walnut and Maple Old Fashioned recipe

Another seasonal take on the Old Fashioned, this cocktail showcases rich, festive flavors. Stir together bourbon, maple syrup, walnut bitters, and a cup of ice in a mixing glass. Once chilled, strain the liquid into a serving glass, and top with a cracked walnut.

THE CRANBERRY APPLE HOT TODDY

The Cranberry Apple Hot Toddy recipe

This warm, crisp drink will carry you through the colder days of fall, when all you want to do is stay inside. Two autumnal fruits are included in this cocktail: apple and cranberry. Heat both fruits in a saucepan with lemon juice, then stir in honey until dissolved. Pour the mix into a serving glass, add bourbon, and stir. If you’re feeling fancy, garnish with apple slices and a star anise pod.