Paul Kushner
Nothing says fall quite like bourbon. It’s perfect for sipping on a crisp autumn night. Bourbon has complex tasting notes including caramel, vanilla, oak, and spice. Combine them with other fall favorites including apple cider, maple syrup, pumpkin, pear, cranberry, fig, cinnamon, and other ingredients and you’ve got a winning combination. That’s exactly what I did to create a list of bourbon cocktails perfect for fall.
There are classics that are sure bets, creative takes on an Old Fashioned, some fruity smashes, and even after-dinner libations. Some are refreshing and light; others are bold and spiced for savoring. Each highlights the best of what bourbon has to offer without being too difficult to make at home.
No matter the occasion, a relaxing evening in, catching up with friends, your next dinner party or fall-themed get together, Thanksgiving, I’m certain you’ll find the perfect bourbon cocktail to fit the chill, relaxing vibe that is fall. Pick your favorite, grab the ingredients, and give one a try.
Bourbon Pear Cider
Bourbon Pear Cider is an autumnal delight. Bourbon is mixed with apple cider and pear sage syrup, then finished off with sparkling club soda to keep the drink light and refreshing. Serve with an optional cinnamon sugar rim, then garnish with a thin slice of pear and some fresh sage leaves. A perfect holiday cocktail for Thanksgiving, a weekend party, or just a quiet evening in.
Bourbon Pear Cider
Ingredients
Method
- In a rocks glass, pour the bourbon and pear sage syrup.
- Add the apple cider and soda water to the glass, stirring well to combine all the ingredients.
- Fill the glass with ice to chill the cocktail.
- For an extra touch of flavor and presentation, sprinkle the top with a mixture of cinnamon and sugar.
- Garnish with a slice of pear and a few fresh sage leaves to enhance the drink’s aroma and appearance.
- Serve immediately and enjoy your refreshing Pear Cider Cocktail!
Maple Cranberry Bourbon
The tartness of cranberry juice and sweetness of maple syrup balance the oak, vanilla, and caramel flavors of bourbon beautifully in this festive cocktail. Club soda adds some sparkle and keeps the drink from being too rich. Garnish with sugared cranberries and a sprig of rosemary, then serve during Thanksgiving and the rest of the winter holiday season. TIP: Make this cocktail’s liquid components ahead of time, then add ice, club soda, and a garnish when you’re ready to serve. Easy peasy. It only takes a few minutes to make too.
Maple Cranberry Bourbon
Ingredients
Method
- Fill a cocktail shaker with ice and add the bourbon, cranberry juice, and maple syrup.
- Shake vigorously until well-chilled.
- Strain the mixture into a rocks glass filled with fresh ice.
- Top with a splash of club soda for a refreshing finish.
- Garnish with maple cranberries and a sprig of rosemary to enhance the festive presentation.
Spicy Bourbon Pumpkin Smash
Looking for a batch boozy punch this year? This recipe for Spicy Bourbon Pumpkin Smash is a breeze to make ahead of time. Bourbon is mixed with pumpkin puree, maple syrup, pumpkin pie spice, vanilla, a little orange juice and bitters so the drink doesn’t feel too heavy, plus a hint of salt to bring all of the flavors together. Serve with ice, cinnamon sticks, a couple of star anise for presentation, plus a splash of ginger beer if you like some fizz and bite. Perfect for a Halloween party, Friendsgiving, Thanksgiving, or any get-together that calls for a seasonal, boozy punch. TIP: Make ahead of time and keep chilled. Add ice, a splash of ginger beer, and garnish when ready to serve.
Spicy Bourbon Pumpkin Smash
Ingredients
Method
- In a punch bowl, combine the spiced pumpkin syrup by mixing together the maple syrup, water, pumpkin puree, pumpkin pie spice, vanilla extract, and a pinch of sea salt.
- Stir in the bourbon, orange juice, and orange bitters until everything is well combined.
- Chill the mixture in the refrigerator until ready to serve.
- Just before serving, add ice to the punch bowl.
- Top with ginger beer for a refreshing, bubbly finish, if desired.
- Serve in glasses and enjoy the spicy, warming flavors of this festive punch.
Pear Bourbon Smash
Pear Bourbon Smash is a riff on the popular Bourbon Smash cocktail. The tartness of lemon juice cuts through the sweetness of maple syrup beautifully in this boozy libation. Mashing the pear and then straining it creates a different flavor profile than most apple-based smash cocktails, being lighter, softer, and perfect for early autumn when fresh pears are abundant. Finish off this easy-to-make libation with a couple of drops of vanilla, a little allspice, then serve on top of crushed ice garnished with a slice of pear or a cinnamon stick if you don’t have pears on hand.
Pear Bourbon Smash
Ingredients
Method
- Begin by slicing the pear in half and removing any overly soft pulp, seeds, and the stem.
- Roughly dice the pear and place it in a medium bowl.
- Mash the pear thoroughly using a fork or a potato masher until it is well broken down.
- Transfer the mashed pear into a fine mesh strainer set over a wide-mouthed measuring cup or another bowl. Press the pear pulp firmly against the strainer to extract as much juice and pulp as possible.
- Once you have extracted the pear juice, add the bourbon, maple syrup, lemon juice, vanilla extract, and allspice to the juice.
- Add ice to the mixture and stir vigorously until all ingredients are well combined and chilled.
- Fill two glasses with ice and evenly divide the pear bourbon mixture between them.
- Serve immediately and enjoy the warm, spiced flavors of this autumnal cocktail.
Persimmon Old Fashioned
Bourbon, persimmon syrup, and bitters are stirred together with ice in a mixing glass to create this seasonal, Persimmon Old Fashioned cocktail. Serve on top of ice garnished with a slice of persimmon, a couple of star anise, and if you’re feeling fancy, anise seed salt rimmed glasses. Perfect for peak persimmon season in the latter part of autumn. This is the perfect cocktail to enjoy before dinner, after Thanksgiving, or on a quiet, relaxing evening. TIP: You can easily make the persimmon syrup ahead of time (see recipe) to save yourself a few steps when you’re ready to create these delicious libations.
Persimmon Old Fashioned
Ingredients
Method
- In a mixing glass, combine the bourbon, persimmon syrup, and orange bitters.
- Fill the mixing glass with ice and stir until well-chilled.
- Strain the mixture into a rocks glass over a large ice cube or fresh ice.
- Garnish with a slice of persimmon and a star anise pod.
- Serve and savor the warm, spiced flavors.
Fig Old Fashioned
This boozy, simple cocktail made with bourbon, jammy figs, and bitters is perfect to sip on top of a big, beautiful, slowly-melting ice cube. Serve with an orange peel twisted over the drink to release its aromatics as garnish, plus a fig slice if you’re feeling fancy! Perfect for an easy-to-make cocktail during early fall when figs are plentiful! Serve after dinner or enjoy it as a relaxing nightcap!
Fig Old Fashioned
Ingredients
Method
- In a mixing glass, add ice, bourbon whiskey, fig simple syrup, and 2 dashes of Angostura bitters.
- Stir for about 15–20 seconds.
- Strain the mixture into an old-fashioned glass with an ice ball.
- Garnish with a fresh fig.
Pecan Bourbon Old Fashioned
This boozy bourbon cocktail features bourbon, pecan liqueur and pecan bitters to accentuate the bourbon’s toasted pecan notes. Rather than traditional simple syrup, brown sugar brings a deeper, more interesting sweetness to the cocktail. Pecan bitters amplify the bourbon’s toasted notes without making this fall bourbon cocktail too heavy. Serve this bourbon cocktail over a large ice cube and garnish with orange peel and a candied pecan. Sip this bourbon cocktail after Thanksgiving dinner alongside a slice of pie, some roasted pecans or a plate of sharp cheeses.
Bourbon Pecan Old Fashioned
Ingredients
Method
- In a cocktail mixing glass, combine the light brown sugar, pecan bitters, water, and bourbon. Stir until the sugar has fully dissolved.
- Once the sugar has melted into the mixture, stir in the pecan liqueur.
- Place a large ice cube into a double rocks glass.
- Add a strip of orange peel to the glass for a bright citrusy garnish.
- Pour the pecan bourbon old fashioned over the ice.
- Top with a candied pecan for an extra touch of sweetness, if desired.
- Serve immediately and enjoy the rich, nutty flavors of this elegant Pecan Bourbon Old Fashioned.
Maple Bourbon Espresso Martini
Coffee and bourbon are a match made in cocktail heaven. Freshly-brewed espresso shaken with bourbon and a couple other ingredients makes one heck of a frothy cocktail. Maple syrup is the perfect addition to highlight the bourbon’s caramel and vanilla notes. Pinch of salt brings out the bourbon’s sweetness and dusting of cinnamon adds a hint of holiday. Serve this boozy bourbon cocktail up in a coupe glass and garnish with three espresso beans.
Maple Bourbon Espresso Martini
Ingredients
Method
- Brew your fresh espresso, cold brew, or extra strong brewed coffee and let cool for a couple minutes
- Pour your espresso, bourbon, Kool-Luah coffee liqueur, maple syrup, cinnamon and sea salt to a shaker tin.
- Add ice and vigorously shake for 30-40 seconds to achieve a thick layer of foam on top
- Strain your cocktail into a coupe glass. For an even better foam, double strain the cocktail.
- Garnish with three espresso beans, serve immediately, and enjoy your Maple Bourbon Espresso Martini using the best Lebowski’s Kool Luah coffee liqueur!
Pomegranate Bourbon Smash
Pomegranates are one of my favorite fall fruits, so when I saw this gorgeous and festive bourbon cocktail I knew I had to try it. Bright red pomegranates add a beautiful garnish to this tart and bubbly bourbon cocktail. Bourbon is balanced by pomegranate and lemon juices and a touch of simple syrup to round out the tartness but not overpower the bourbon. Garnish with a handful of pomegranate seeds tossed on top of the cocktail.
Pomegranate Bourbon Smash
Ingredients
Method
- Muddle Mint: In a cocktail shaker, add a few fresh mint leaves and the simple syrup. Gently muddle the mint to release its aroma and flavor.
- Add Liquids: Add the bourbon, pomegranate juice, and fresh lemon juice to the shaker.
- Shake: Fill the shaker with ice and shake vigorously for about 15 seconds.
- Strain and Serve: Strain the mixture into a rocks glass filled with ice.
- Garnish: Garnish with a few pomegranate seeds and a sprig of fresh mint.
- Enjoy: Serve immediately and enjoy your refreshing Pomegranate Bourbon Smash.
Vanilla Chai Old Fashioned
This easy-to-make bourbon cocktail combines three secret weapons of holiday cocktails: warm spices, caramelized vanilla and bright citrus. Homemade vanilla chai syrup brings cinnamon, cardamom and other spices to the forefront of this Old Fashioned, and a squeeze of lemon juice keeps the cocktail balanced. Angostura bitters are the cherry on top of this boozy bourbon cocktail. Garnish with cinnamon stick, star anise and orange slice. Make ahead vanilla chai syrup makes this bourbon cocktail come together in a few minutes.
Vanilla Chai Old Fashioned
Ingredients
Method
- Bring 1 cup of water to a boil in a small pot.
- Remove from heat, add chai tea bags, cover, and steep for 10–15 minutes.
- Discard the tea bags, then stir in the sugar while the tea is still warm.
- Bring the mixture back to a gentle simmer for about 3 minutes, then remove from heat.
- Stir in vanilla extract and let it cool completely. Store in the refrigerator for up to 2 weeks.
- In a mixing glass, add bourbon, lemon juice, bitters, and chai syrup.
- Fill with ice and stir until well chilled.
- Strain into a rocks glass with a large ice cube.
- Garnish with a cinnamon stick, star anise and orange slice.
Wild Turkey Thanksgiving Cocktail
Whiskey Sours are the easiest cocktails to make, requiring just a combination of bourbon, fresh-squeezed lemon juice and simple syrup then shaken with ice and you’re done! Fresh lemon juice helps cleanse your palate between bites of rich, tasty foods making it the perfect bourbon cocktail to enjoy over the holidays. Bold notes of Wild Turkey whiskey make this boozy bourbon cocktail just the ticket for Thanksgiving or other holidays. Garnish with lemon peel twist and serve over ice with Thanksgiving appetizers or before dinner.
Wild Turkey Thanksgiving Cocktail
Ingredients
Method
- In a cocktail shaker, add the bourbon, lemon juice, and simple syrup.
- Add ice to the shaker and shake vigorously for 25 to 30 seconds.
- Place larger ice cubes in your serving glass.
- Strain the cocktail mixture over the ice in the prepared glass.
- Enjoy your Wild Turkey Thanksgiving Cocktail!
Smoked Cinnamon Apple Cider Bourbon Smash
The secret behind this boozy bourbon cocktail is smoke. Set a lit cinnamon stick or a small thyme sprig if you have one on top of an inverted glass to trap the smoke. Then, build the rest of the bourbon cocktail in the same glass, as smoke and apple cider are a match made in fall cocktail heaven! Bourbon and apple cider go hand-in-hand so there’s nothing fancy going on here, just a few easy-to-find ingredients come together to make a tasty bourbon cocktail. Orange bitters highlight bourbon’s natural orange peel notes and agave (totally optional) balances the cocktail’s tartness.
Smoked Cinnamon Apple Cider Bourbon Smash
Ingredients
Method
- To infuse your cocktail with a smoky flavor, take a fresh cinnamon stick (or sprig of thyme) and place it on a plate or wooden plank. Using a lighter, carefully ignite the end of the cinnamon stick or thyme until it begins to smoke. Place your cocktail glass over the smoking cinnamon stick or thyme to capture the aroma inside the glass. Let it sit for a few moments to absorb the smoke.
- While the glass is smoking, fill a cocktail shaker with ice.
- Add the apple cider, bourbon, orange bitters, and agave syrup (if using) to the shaker.
- Shake vigorously until the mixture is well-chilled and fully combined.
- Remove the smoking element from the glass and pour the shaken cocktail into the prepared glass.
- Garnish with fresh thyme, a cinnamon stick, and/or apple slices. For an extra smoky experience, you can lightly char the garnish with a lighter before adding it to the drink.
- Serve immediately and enjoy the rich, smoky flavors of this autumn-inspired cocktail.
Pumpkin Old Fashioned
This Old Fashioned features maple syrup in place of simple syrup, a spoonful of pumpkin puree, and pumpkin spice that includes cinnamon, nutmeg, and clove. Shaking this drink helps distribute the puree for a smooth consistency. Top it off with a cinnamon stick and a cherry to make this drink both flavorful and visually impressive. This bourbon-based fall cocktail is the perfect fit for a Halloween or Thanksgiving cocktail or a cozy, cold evening.
Pumpkin Old Fashioned
Ingredients
Method
- In a cocktail shaker, combine the bourbon, orange liqueur, maple syrup, pumpkin puree, and aromatic bitters. Shake well to combine.
- Strain the mixture through a fine-mesh strainer into an old-fashioned glass filled with ice.
- Garnish with an orange peel or rosemary sprig, and serve.
Maple Bacon Old Fashioned
This Old Fashioned recipe uses maple syrup in lieu of sugar. The sweetness of maple pairs well with the caramel, oak, and vanilla flavors in bourbon. Garnish it with a strip of bacon that’s cooked until crispy and salty, adding another dimension to this drink. The bacon also doubles as a snack, making this cocktail the ultimate boozy accompaniment for a fall brunch, a visit to your backyard fire pit, or an unusual pairing with a heartier appetizer for those who prefer savory over fruity.
Maple Bacon Old Fashioned
Ingredients
Method
- Pour the bourbon, maple syrup, and both bitters in a cocktail mixing glass filled with ice.
- Stir until well-chilled.
- Strain the mixture into an Old Fashioned glass over a large hunk of ice.
- Garnish with a slice of bacon and cocktail cherries.
Cider and Maple Old Fashioned
Bourbon, apple cider, maple syrup, and bitters come together in this delectable fall cocktail that’s perfect for a casual get-together. Apple cider is a classic accompaniment for fall. It’s delicious on its own and also acts as a perfect pairing with bourbon-based fall cocktails, muting the whiskey flavor just enough, but never drowning it out. Garnish the drink with a cinnamon stick and adjust the sweetness to your preference to create a crowd-pleasing pre-dinner drink.
Ingredients
- 2 oz bourbon
- 3/4 oz apple cider
- 1/3 oz pure maple syrup
- 2 to 3 dashes orange bitters
- 1 cinnamon stick, for garnish
- Ice
Autumn Apple Bourbon Cocktail
The boozy bourbon base ensures this cocktail won’t taste too light despite its fall-inspired apple and spice flavors. Make your own cinnamon syrup ahead of time and refrigerate it for easy fall cocktails in a jiffy. Apple cider lends a fall-inspired fruitiness to the drink. Serve this drink at your next Thanksgiving get-together or a casual fall dinner.
Ingredients
- 2 oz bourbon
- 1 1/2 oz cloudy apple cider
- 1/2 oz fresh lemon juice
- 1/3 oz cinnamon syrup
- 2 dashes Angostura bitters
- Apple slice, for garnish
- Cinnamon stick, for garnish
- Ice
Juicy Apple Bourbon Fall Cocktail
Maple syrup and Honeycrisp apple juice bring sweetness to this simple yet flavorful bourbon-based fall cocktail. Lemon peel garnishes add a zing of citrus to this boozy fall libation to cut through the sweet notes of maple and apple. Garnish it with a lemon peel or an apple slice and serve at your next fall brunch or casual get-together as a pre-dinner cocktail.
Ingredients
- 2 oz bourbon
- 2 oz Honeycrisp apple juice
- 1/2 oz simple syrup
- 1/4 oz fresh lemon juice
- 1 tsp pure maple syrup
- 2 thin red apple slices, for garnish
- Ice
- Optional splash of sparkling water
The Clove and Cider – A Bourbon Cocktail
A unique cocktail that’s sure to impress guests at your next get-together, this bourbon-based fall cocktail features apple cider and a syrup that’s prepared with cloves, sugar, and water. Lemon juice adds a touch of tartness to the cocktail that complements the sweet, spiced flavors. Garnish the cocktail with a smoked cinnamon stick and serve by the fire with friends or family or as part of your next Thanksgiving celebration.
Ingredients
- 2 oz bourbon
- 3/4 oz amaro
- 2 1/2 oz apple cider
- 1/2 oz clove simple syrup
- 1/2 oz fresh lemon juice
- 1 cinnamon stick, for smoking and garnish
- Ice
For the Clove Simple Syrup
- 1 cup water
- 1 cup sugar
- 1 1/2 tbsp whole cloves
Rabbit Hole Bourbon “Fall Back” Cocktail
Apple cider adds a touch of fall-inspired flavoring to this easy-to-make bourbon-based fall cocktail. Simple syrup, or maple syrup if you’re feeling adventurous, adds a little sweetness and Grand Marnier lends some boozy orange flavoring to the drink. A squeeze of fresh lemon juice adds a final flourish and prevents this cocktail from being too sweet while ensuring a refreshing, crisp finish. Garnish with an apple slice or a cinnamon stick and serve at your next boozy get-together this fall.
Ingredients
- 2 oz bourbon
- 1/2 oz Grand Marnier
- 1/4 oz Campari
- 1 1/4 oz apple cider
- 1/2 oz fresh lemon juice
- 1/3 oz simple syrup
- Apple slices, for garnish
- Ice
Cinnamon Maple Whiskey Sour
This whiskey sour features equal parts bourbon and fresh lemon juice for a citrusy, boozy kick. Maple syrup balances out the acidity of the lemon, while a sprinkle of cinnamon gives this cocktail a deliciously cozy aroma. Serve this bourbon cocktail over ice and garnish with a lemon wheel or cinnamon stick. Feel free to add more or less maple syrup based on your preferred sweetness, where less syrup means a bourbon-forward cocktail.
Ingredients
- 2 oz bourbon
- 3/4 oz fresh lemon juice
- 1/2 oz pure maple syrup
- 1 small pinch ground cinnamon
- Lemon wheel or cinnamon stick, for garnish
- Ice
Apple Cider Bourbon Cocktail
This easy-to-make bourbon cocktail is the ultimate twist on an Old Fashioned. Fresh apple cider is the star of this recipe, balanced with a splash of apple cider vinegar so it’s not too sweet. Orange bitters, maple syrup, and a hint of cinnamon round out this bourbon drink perfectly. We love this cocktail’s fruity notes, making it the perfect alternative to a classic Old Fashioned recipe. Garnish your drink with a slice of apple or cinnamon stick.
Ingredients
- 2 oz bourbon
- 2 1/2 oz apple cider
- 1/2 oz fresh lemon juice
- 1/3 oz pure maple syrup
- 2 dashes orange bitters
- Small pinch ground cinnamon
- Small pinch ground allspice
- 1 oz club soda, optional
- Apple slice, for garnish
- Cinnamon stick, for garnish
- Ice
Cozy Maple Pumpkin Bourbon Cocktail with Apple Cider
With real pumpkin puree, this bourbon cocktail will surely impress. The apple cider adds a crisp, fall-inspired note to this recipe, while maple syrup and cane sugar balance out the strong notes of the bourbon. Serve this boozy apple cider drink cold and garnish with apple slice or a cinnamon stick. Pumpkin spice (optional) amps up the cinnamon, clove, and nutmeg notes in this drink. The pumpkin gives this bourbon apple cider drink a distinct, seasonal taste and creates a thicker, more luscious texture. This drink recipe can easily be doubled, tripled, but we’ve written it for a single-serving.
Ingredients
- 2 oz bourbon
- 2 oz apple cider
- 2 tsp pumpkin puree
- 1 1/2 tsp pure maple syrup
- 1/4 tsp pumpkin spice
- 2 dashes orange bitters
- Cinnamon sugar, for the rim, optional
- Apple slice, for garnish
- Cinnamon stick, for garnish
Fall-Spiced Old Fashioned Cocktail
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This old fashioned gets a fall-inspired twist with maple syrup infused with star anise, cinnamon, and vanilla bean. We suggest a bourbon with high-rye content because rye’s peppery flavor pairs well with the spiced maple syrup. The addition of bitters gives this cocktail that Old Fashioned flair. Serve over a large ice cube and garnish with a cinnamon stick or orange peel.
Ingredients
- 2 oz spiced bourbon
- 1/4 oz pure maple syrup
- 2 dashes Angostura bitters
- 1 tsp water
- Orange peel, for garnish
- 1 large ice cube
For the Spiced Bourbon
- 2 cups bourbon
- 1 cinnamon stick
- 1/2 vanilla bean, split lengthwise
- 1 whole star anise
- 6 whole cloves
Cider-Bourbon Cocktail
Apple cider takes center-stage in this simple-to-make cocktail. Bourbon has natural notes of caramel, vanilla, and oak. The addition of fresh lemon juice adds some acidity and ensures that the cider’s sweet notes don’t take over. Ginger adds a warm, spicy kick without having to seek out hard-to-find syrups or liqueurs.
Ingredients
- 3 oz apple cider
- 2 oz bourbon
- 1/2 oz fresh lemon juice
- 2 thin slices fresh ginger
- 1 thin apple slice, for garnish
- Ice
The Cranberry Apple Hot Toddy
This hot toddy is the ultimate accompaniment to a cold-weather evening. Cranberry and apple juices form a cozy, fruity foundation for this bourbon cocktail, balanced out with bourbon, honey, and a squeeze of lemon. Star anise lends a subtle, sweet-spicy licorice flavor and aroma. We love this cocktail served in a mug after Thanksgiving dinner or on a chilly fall night by the fire.
Ingredients
- 2 oz bourbon
- 2 1/2 oz cranberry juice
- 2 1/2 oz apple juice
- 2 tsp honey
- 1/2 oz fresh lemon juice
- 1 star anise pod, for garnish
- Thin apple slices, for garnish
Bourbon Sour
This bourbon cocktail skips pumpkin, apple cider, maple syrup, and other seasonal ingredients, relying on standard pantry items to create a crowd-pleaser. Serve this drink over ice and garnish with a twist of orange for an added kick of citrusy aroma. You’re sure to love this simple and reliable bourbon cocktail, a classic recipe that balances sweet and sour elements!
Ingredients
- 2 oz bourbon
- 3/4 oz fresh lemon juice
- 1/2 oz simple syrup
- Orange slice, for garnish
- Maraschino cherry, for garnish
