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Cigars and Fall Cocktails Pairings

Shane K. K's picture

Shane K.

For many, autumn is the ultimate season for cigar smoking. It’s back to leather jackets and leaving the windows open a crack at night. Tune in some football and turn up the fireplace. And who doesn’t have a favorite hooded sweatshirt? You can’t have fall without cigars, and a good cigar always tastes best with a drink to go with it. Here are three amazing pairings of cigars and fall cocktails you can put together in your man cave, or order the next time you’re sitting in your favorite cigar bar.

1.  Ashton ESG & Jack Rose

Legendary cigar-maker Carlito Fuente blends Ashton ESG (Estate Sun Grown) from reserves of the rarest and oldest tobaccos grown on the Fuente family’s iconic Chateau de la Fuente Estates in the Dominican Republic. A glistening Dominican Sun Grown wrapper envelops perfectly matured binder and filler tobaccos in five classic shapes. Tasting notes of cedar, graham cracker, and molasses emerge with velvety spices.

The 94-rated cigar is a luxurious complement to a Jack Rose, a classic Roaring 20s-era cocktail made with apple brandy and grenadine. Sweet, citrusy, and refreshing flavors of apple and pomegranate harmonize nicely with the milky spices and luscious aftertaste of Ashton ESG.


  • 2 oz Apple brandy
  • 1 oz Fresh Lemon juice
  • ½ oz Grenadine
  • Garnish: Brandied cherry

Glass: Coupe glass

Preparation: Combine all ingredients in a shaker with ice. Shake until chilled. Fine-strain into glass and garnish with brandied cherry.

2.  My Father Le Bijou 1922 & Maple-Ginger Manhattan

In 2015, Cigar Aficionado awarded My Father Le Bijou 1922 a 97-point rating and named it their ‘#1 Cigar of the Year.’ A robust and peppery profile is drawn from an ultra-oily Ecuador Habano wrapper and a potent blend of premium Nicaraguan binder and filler tobaccos grown on select Garcia family estates. Full-bodied notes of black pepper, leather, earth, and espresso beans mesmerize the senses with spicy composure.

The sweet and invigorating flavor in a Maple-Ginger Manhattan rises to the occasion to keep up with the smoky character of the cigar. Smooth and boozy notes of maple and ginger snaps blanket the palate with a dense, viscous bliss. Its deep buttery taste is an excellent backdrop to the sharp, peppery profile of Le Bijou 1922. 


  • 1 ½ oz Bourbon or rye
  • 1 oz Vermouth
  • 2 dashes of bitters
  • ½ oz Maple syrup
  • ½ oz Ginger Liqueur
  • Garnish: Brandied cherry

Glass: Martini glass

Preparation: Combine all ingredients in a cocktail shaker with ice. Stir for 30 seconds. Strain into a martini glass. Garnish with brandied cherry.

3.  Arturo Fuente Anejo & Pumpkin Spice Old Fashioned

A lustrous Connecticut Broadleaf wrapper is aged in a cognac barrel before it’s placed over a vintage interior of premium Dominican tobaccos blended by master cigar-maker Carlito Fuente. Abundant notes of dark chocolate, wood, vanilla, and coffee beans, accompany buttery spices from beginning to end. The most popular shape is the elusive No. 77 Shark, but Arturo Fuente Anejo is also crafted in a number classic sizes.

The cigar’s sweet impressions of cognac and cocoa are perfect for an evening in front of the hearth with a Pumpkin Spice Old Fashioned in your hand. Dashes of orange bitters and cinnamon add zesty hints to pumpkin flavors that make your bourbon as savory as ever. Arturo Fuente Anejo is ideal with its dark cloying taste, silky aroma, and robust finish. If you’ve got a tufted leather armchair to kick back in with a cigar, you’ll be sitting pretty this fall.


  • 2 oz Bourbon
  • 1 oz Maple syrup
  • ½ oz Orange-flavored liqueur
  • 2 dashes of orange bitters
  • 2 tablespoons pumpkin puree
  • 1 Orange slice
  • 1 dash Club Soda
  • Garnish: Cinnamon stick

Glass: Rocks glass

Preparation: Combine maple syrup, orange liqueur, pumpkin puree, orange bitters, and orange slice in a rocks glass and muddle. Add bourbon with one large ice cube and a splash of club soda. Stir several times with a cinnamon stick.

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