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12 Classic Bourbon Cocktails for Toasting Fall

Pour one out for National Bourbon Heritage Month.

September brings us the official end of summer. But it also heralds the beginning of my favorite season: Fall. What better way to get in the mood for fall than to celebrate while sipping some beautiful bourbon cocktails? After all, September also happens to be, officially, National Bourbon Heritage Month, a period dedicated to honoring the family heritage and deep-rooted legacy that the Bourbon industry contributes to the United States. "Kentucky is the one, true and authentic home for America's only native spirit," reads The Kentucky Bourbon Trail's web site.

So, in honor of our lovely native spirit, I've put together this list of twelve to-die-for Bourbon cocktails that are sure to warm your bones as the weather cools down. Some were crafted for us here at Best Life, while others are classics we all know and love. Now, spark the fireplace, whip one of these up, and get ready to fall into fall!

Iced Bourbon Palmer

bourbon cocktails bourbon palmer

Crafted by Shana Wall

I love sipping on iced tea and lemonade, so I figured we should elevate the classic combo a notch in honor of National Bourbon Heritage Month. This is my take on a boozy Arnold Palmer.


  • 12 oz Makers Mark Bourbon
  • 2 cups boiling water
  • 8 oz Honey Syrup
  • 3 Orange Pekoe Tea Bags
  • 6 black tea bags
  • 2 cups fresh lemonade
  • Ice
  • Raw sugar for rim
  • Fresh mint sprigs and orange slices for garnish


To infuse the bourbon:

Place 3 Orange Pekoe Tea Bags in a large Mason jar or container with a lid. Pour Bourbon in and close lid tightly. Steep in refrigerator for 24 hours.

To make the cocktails

Pour the boiling water over the Black Tea Bags in a heatproof container and steep for 5 minutes. Remove tea bags and discard. Pour the tea base into a heatproof pitcher or serving jar. Add the honey syrup and stir well. Add the lemonade, ice, and bourbon. Stir well, and refrigerate until serving. To serve, pour into an ice-filled highball glass or Old Fashioned glass. Rub an orang wedge around the glass then rim with brown sugar. Garnish with mint and orange slices. (*Add more honey syrup to taste.) Serves 8.

Bourbon Maple Chai Punch

Bourbon Maple Chai Punch bourbon cocktails

Crafted by John Henderson of The Happiest Hour 

"The chai and maple add a nice sweetener which compliment Maker's Mark's sweeter flavor profile," Henderson tells me. Plus, the apples make this libation quite the seasonally appropriate treat!


  • 1 ½ part Maker's Mark Bourbon
  • 1 part Apple Cider
  • 1 part Hard Cider
  • 1 part strong Chai Tea
  • ¾ part Lemon Juice
  • ¾ part Maple Syrup
  • 2 parts Sater, (can use sparkling too for more effervescence)
  • 2 dashes Fee Brothers West Indies Orange Bitters
  • Garnish bowl with Apple Slices, Lemon Slices, and Cinnamon Sticks if desired.


Combine all ingredients in punch bowl and ladle into cups over ice. Serves 1.

Family Meal

MM Family Meal on bourbon cocktails

Crafted by Chef Newman Miller, Star Hill Provisions at Maker's Mark Distillery

"The Family Meal cocktail is similar to what restaurant folks sometimes drink without bourbon as a 'meal' between double shifts. The jolt of caffeine between the cold brew coffee concentrate and Mexican coke do just the trick," says Miller. "Using Maker's Mark as the base of this cocktail evens that out for a surprisingly delicious and simple cocktail all folks can enjoy at any point in the day."


  • 1 ½ parts Maker's Mark Bourbon
  • ¼ part cold brew coffee concentrate (Chef Newman uses Harden coffee, which is house roasted 15 miles from restaurant)
  • Mexican Coke, as needed
  • Lemon Peel, for garnish


Build coffee and Maker's Mark Bourbon in a rocks or highball glass. Add ice and stir gently. Top with Mexican cola and finish with oil from a strip of lemon peel. Serves 1.

Tailor Made

tailor made bourbon cocktails

Crafted by Pam Wiznitzer, bartender, mixologist, and creative director at Seamstress

"Earl Grey and nutmeg compliment Maker's Mark nicely for a smooth fall libation," Wiznitzer says. 



Combine all ingredients in a punch bowl and allow the ingredients to marry for a few hours. When ready to serve, add a large ice block, garnish with fresh nutmeg, and ladle out into individual punch cups. Serves 8.

Bourbon Sangria

Sangria, cocktails

I always love a good sangria. Here's a tastier, punchier version with a Bourbon twist. Enjoy!


  • 1 Bottle Malbec
  • ½ cup Bourbon
  • 1 Apple Diced
  • 1 can Mandarin Oranges
  • 1 Cinnamon Stick
  • ½ cup Sprite


Drop the fruit into the bottom of a large pitcher. Add the cinnamon stick. Pour wine over the fruit, then add the bourbon and stir. Refrigerate for anywhere from 3 hours to 3 days. When ready to serve, pour into a glass filled with ice and top with Sprite. Serves 6.

Bourbon Mary

Bloody Mary, cocktails


We all love a good Bloody Mary during summer brunches. But there's no reason the tradition can't carry into fall. Swap out vodka for Bourbon and you've got a sublime cocktail.


  • 12 oz Makers Mark Bourbon
  • 2 dashes hot sauce
  • 2 dashes Worcestershire sauce
  • 1 tsp wasabi
  • Tomato juice
  • 1 lime wedge
  • Celery salt


Rub the lime wedge around the rim of a pint glass and coat with celery salt. Fill with ice and add 2 dashes of celery salt and the remaining ingredients except the tomato juice. Fill with tomato juice and stir well. Garnish with a celery stalk, lime wedge and blue cheese-stuffed olives. Serves 1.

Kentucky Cobbler

KentuckyCobbler bourbon cocktails

Crafted by Tarin Fasano, bartender at The Spotted Pig

I was sitting at one of my favorite local New York City bars, The Spotted Pig, speaking to one of my favorite bartenders, Tarin, when I was writing this story. I asked her if she would craft me a bourbon cocktail to try out, and she whipped this up. And I drank it up!


  • 3 Bourbon-soaked cherries
  • 3 orange slices
  • 0.5 oz raspberry preserves
  • 0.5 oz orange juice
  • .75 oz lemon juice
  • 1 oz Colosia Amartillado Sherry
  • 1.5 oz Virgilkaine Rip-Track Bourbon


Muddle cherries and orange slices. Add everything to a cocktail shaker. Shake vigorously and double-strain over ice into rocks glass. Serves 1.

Old Fashioned

Nightcaps, old fashioned

From The Today Show

I've tried a million Old Fashioned recipes, and this is among the best out there. Can't go wrong with the classic!


  • 1 sugar cube
  • 2 dashes Angostura bitters
  • 2 ounces bourbon or rye
  • Orange twist, no pith


In an old-fashioned short rocks glass, muddle the sugar, bitters, and a spoon of warm water until the sugar is dissolved. Add the rye or bourbon and stir. Add one large ice cube. Twist the orange peel to release the oils and run around the rim of the glass, then drop the twist into the glass and enjoy.

Hot Toddy

Nightcaps, hot toddy

From Epicurious

I love a Hot Toddy on a crisp fall night to warm me up! Plus, you can carry this tasty recipe with you through the winter.


  • 1 oz (2 tablespoons) Bourbon
  • 1 tbs mild Honey
  • 2 teaspoons fresh Lemon Juice
  • 1/4 cup boiling-hot Water


Put bourbon, honey, and lemon juice in a 6-ounce mug. Top off with hot water and stir until honey is dissolved. Serves 1


A Manhattan, a truly timeless cocktail.

Crafted by Tarin Fasano

No introduction is needed for this classic. Here's the perfect recipe—straight from Tarin Fasano at The Spotted Pig.



Chill a coup glass in freezer for at least 5 minutes. Shake the whiskey, and both vermouths in a cocktail shaker filled halfway with ice. Strain into chilled coup glass. Add the dash of bitters, and garnish with a Luxardo Maraschino Cherry. Serves 1

Bourbon Sour

bourbon cocktails bourbon sour

Crafted by Tarin Fasano

"You can never go wrong with a classic Whiskey Sour. Of all the ones I've tried is one here is my favorite rendition!


  • 2 oz Bulleit Bourbon
  • ¾ oz freshly squeezed lemon juice
  • Lime juice
  • 0.5 oz simple syrup (see below for recipe)
  • 1 egg white
  • Maraschino cherries

Recipe for simple syrup:

Simple Syrup: Put 1 cup sugar and 1 cup water in a small saucepan and cook over medium heat until the sugar dissolves. Chill thoroughly before using.


In a cocktail shaker, add the egg white, bourbon, lemon juice, and simple syrup and dry shake to emulsify the egg. Add ice, then do a second shake. Double-strain over a rocks glass filled with ice. (It is important to double-strain so that you get the right ratio of foam-to-liquid.) Garnish with a Maraschino Cherry and a splash of Angostora Bitters. Serves 1.

Mint Julep

From The Food Network's Alton Brown

The one-and-only Alton Brown has perfected the mint julep recipe. For a refreshing kick during a balmy fall day (hey, they come around!), whip one of these up. Cheers!


  • 10 mint leaves, plus a sprig for garnish
  • 1 1/2 teaspoons superfine sugar
  • Seltzer water
  • Crushed ice
  • 2 1/2 ounces Kentucky bourbon whiskey


Place the mint leaves in the bottom of an old-fashioned glass and top with the sugar. Muddle these together until the leaves begin to break down. Add a splash of seltzer water, fill the glass 3/4 full with crushed ice, and add the bourbon. Top with another splash of seltzer, stir, and garnish with a sprig of mint. Serve immediately. Serves 1.

Shana Wall is a certified sommelier, cellar consultant, and contributing editor for Best Life Magazine. Follow her on Instagram or email her at [email protected]For more advice on living your best life, follow us on Facebook now!