As the summer inches nearer to its conclusion and the prospect of sweater weather gets tantalizingly closer, many of us are starting to think about cooler-weather cocktails made with aged brown spirits — specifically whiskey. While you can, and should, drink whiskey all year long, the summer months usually lend themselves to lighter clear spirits, with blanco tequila, gin, white rum, and vodka all finding their way into a variety of refreshing drinks. But fall is the time to break out the bourbon again, a spirit that can be used in countless classic and nouveau cocktails ranging from warm and comforting to bold and brisk. Autumn also happens to be apple picking season, at least in many parts of the country, as orchards erupt with a bounty of apple varieties like Granny Smith, Macoun, Winesap, and Honeycrisp.

This happens to be the perfect confluence of flavors, as whiskey, specifically bourbon, is particularly well suited to pairing with the sweet, tart, and fruity notes that are at the core of an apple’s palate (pun definitely intended). And Bulleit is an exceptionally good whiskey to use when whipping up a batch of apple-based cocktails. The bourbon’s high rye content and lengthy maturation period infuse the palate with notes of spice, oak, and vanilla, making it the perfect complement to apples in any form, from ripe fruit to infused syrups to cider to any distilled apple spirit.

Pair any type of apple: sweet, tart and fruity, with these Bulleit cocktails for the Fall.
Pair any type of apple: sweet, tart and fruity, with these Bulleit cocktails for the Fall.

Apple Old Fashioned

A good place to start your journey into bourbon-apple cocktails is by making an Apple Old Fashioned, a riff on the classic whiskey cocktail that uses Bulleit Bourbon as its base. This is an autumnally augmented version of this OG drink, with the flavors kicked up a notch by the use of apple bitters, a slice of fresh apple, and a bit of applejack for good measure.

Ingredients
1.5 ounces Bulleit Bourbon
.5 ounce apple brandy
1 bar spoon honey
2 dashes aromatic bitters
2 dashes apple bitters
Slice of red apple (Fiji, Macoun, etc.)
Cinnamon stick

Directions

Add honey and bitters to tumbler with a splash of water and stir until combined. Add bourbon and apple brandy, followed by a large spherical ice cube. Stir in glass until cold, then garnish with a slice of apple and cinnamon stick.

Big Apple Manhattan

Another classic whiskey cocktail that can be tailored to the spirit of the fall is the Manhattan. This spirit-forward drink is traditionally made with rye, but Bulleit Bourbon works well here given its high rye mash bill. The spice on the palate provides a buttress to the sweetness from the vermouth and Calvados, a type of French apple brandy, rounding out the flavor profile of this venerable cocktail.

Ingredients 
1 ounce Bulleit Bourbon
1 ounce apple brandy
1 ounce sweet vermouth
2 dashes orange bitters
2 dashes apple bitters
1 slice red apple

Directions

Combine bourbon, apple brandy, and vermouth in a mixing glass. Add bitters and ice, and stir about 30 times until very cold. Strain into coupe glass, and garnish with a slice of apple.

Apple Bourbon Highball

The Highball is a refreshing and simple way to enjoy bourbon. It’s usually made with just a couple of ounces of the whiskey topped off with soda water and garnished with a slice of lemon. But this humble recipe can be adjusted to incorporate apple flavors for the colder months. Add a little hard cider and/or unsweetened regular cider to the drink, and try garnishing with a slice of dried apple instead of fresh fruit.

Ingredients
1.5 ounces Bulleit Bourbon
2 ounces hard cider
.5 ounce unsweetened cider
Soda water
2 dashes ginger bitters
1 slice dried apple

Directions

Fill highball glass with one long ice cube, or several smaller cubes all the way to the top. Add bourbon, hard cider, and unsweetened cider. Then top with soda water and add bitters. Stir until very cold, and garnish with a slice of dried apple.

Apple Whiskey Sour

The Whiskey Sour is a classic cocktail built upon the combination of tart lemon and sweet bourbon, but apple can be used in the drink as well to provide a crisp and fruity twist to turn it into an autumn staple. Also, try using a slice of Granny Smith apple instead of a sweeter red variety; this will provide some balance to the tart citrus and sweet cider used in the drink.

Ingredients
2 ounces Bulleit Bourbon
2 ounces apple cider
.5 ounce simple syrup
.5 ounce fresh lemon juice
1 slice Granny Smith apple

Directions

Combine all the ingredients except the slice of apple in a cocktail shaker and fill with ice. Shake until very cold, about 30 seconds. Then strain into rocks glass and garnish with a green apple slice.

These are just a few cocktail recommendations to get you started, but there’s a whole world of apple-based bourbon drinks to explore from here. Try subbing an apple element into another classic like a Boulevardier, or experiment with flavors using bottles that might be gathering dust at the back of your home bar. Try mixing Bulleit Bourbon with amaro and apple brandy for a version of a Black Manhattan. And don’t forget about winter warmers like hot mulled cider, an easy drink that you can prepare in advance for a group and then just add a shot of Bulleit to each mug as you serve. So when you go apple picking this fall, remember to set some aside to use in these delicious cold-weather cocktails.

This article is sponsored by Bulleit.