Top 5 Bourbon Cocktails to Enjoy This Fall

Ready for some fall cocktail recipes that spotlight bourbon? Good–because we’ve got loads. There’s no better time than autumn for settling in with a new bottle, plus five new recipes for road-testing your latest find. So grab your slippers, get that fire crackling, and read on. 

Brown Derby

Fall marks the start of citrus season, a celebratory time for every cocktail lover. Celebrate these indispensable bar fruits with this bittersweet concoction of bourbon, grapefruit juice, and honey syrup. Just don’t be tempted to substitute the stuff from the carton; freshly squeezed citrus juice will always take your cocktail to the next level (even if it’s just vodka and orange juice). 

To make this cocktail, you’ll need to whip up a quick batch of honey syrup. The good news is that it’s easy and, if you have extra, it keeps in the fridge for weeks.

• 1 ½ ounces bourbon (try Great Jones Straight Bourbon Whiskey)
• 1 ounce freshly-squeezed grapefruit juice
• ½ ounce honey syrup (a 1:1 ratio of honey and water, warmed to dissolve)

Combine all ingredients in a cocktail shaker filled with ice. Shake until well-chilled, then strain into a chilled coupe or Nick & Nora Glass.

Bourbon Sour

A real whiskey sour is one of the most sophisticated cocktails you can make–and bears little resemblance to those teeth-achingly sweet concoctions made with packaged mixers. It’s also a great cocktail for learning how to do a dry shake, a bartending technique that effectively emulsifies egg white into a silky, mousse-like texture. 

• 2 ounces bourbon (try our Mash & Grape exclusive single barrel selection of Elijah Craig)
• ¾ ounce lemon juice
• ½ ounce simple syrup
• ½ ounce egg white
• Angostura bitters, for garnish

Add bourbon, lemon juice, simple syrup, and egg white to a cocktail shaker. Shake, without ice, for at least 30 seconds (pro tip: If you have a Hawthorne strainer, take the spring off and add it to the shaker for extra aeration). Remove the spring if you used it, add ice, then shake again until well chilled. 

Double-strain into a chilled cocktail glass. Garnish the drink with three dots of Angostura bitters, drawing a toothpick through each one to create a heart shape, if desired. 

Maple Old Fashioned

This autumnal twist on the classic Old Fashioned substitutes maple syrup for the sugar cube or simple syrup, plus it incorporates two different kinds of bitters: Angostura and orange. The caramelly, aromatic tones of maple syrup pair particularly well with the sweet tanginess of orange.

• 2 ounces bourbon (Barrell Bourbon Batch 030 is a great option)
• ½ ounce maple syrup
• Dash Angostura bitters
• Dash orange bitters
• Orange twist, for garnish

Add the bourbon, maple syrup, and bitters to a chilled rocks glass. Stir well to combine, then add a large ice cube. Stir again to chill, and garnish with the orange twist.

Perfect Manhattan

In this case, “perfect” isn’t a synonym for “ideal”–even if the Manhattan is among the most flawless bourbon drinks ever created. Instead, it refers to drinks that use a combination of equal parts dry and sweet vermouth. In this case, a dose of dry vermouth takes the standard Manhattan in a slightly drier, more herbaceous direction that feels just right on chilly fall days.

• 2 ounces bourbon (like Ironweed Bourbon Whiskey)
• ½ ounce dry vermouth
• ½ ounce sweet vermouth
• Dash Angostura bitters
• Amarena cherries, for garnish

In a mixing glass filled with ice, combine the bourbon, vermouths, and bitters. Stir until well-chilled, then strain into a coupe glass. Garnish with cherries. 

Hot Toddy

Nothing warms you up after shoveling the sidewalk (or just another long, rainy commute home) like a well-made hot toddy. You can make great toddies with any kind of whiskey, but bourbon is a particularly good choice for pairing with warm spices like cinnamon or nutmeg. 

When you’re making yours, don’t let the water come to a full rolling boil. If it’s too hot, it’ll cause the alcohol in your bourbon to partially evaporate, which will make your drink smell and taste overly boozy. Also, feel free to experiment with the hot water portion by substituting herbal tea (ginger is nice) or hot apple cider.

• 2 ounces bourbon (try Spirit Works Distillery Four Grain Straight Bourbon Whiskey)
• ½ ounce honey (or use 1 ounce honey syrup from the Brown Derby recipe)
• ½ ounce lemon juice
• 6 ounces hot water
• Lemon wedge and cinnamon stick, for garnish

Combine bourbon, honey, hot water, and lemon juice. Stir thoroughly to combine, garnish with lemon wedge and cinnamon stick, and enjoy.