The Perfect Fall Old Fashioned: A Historic Cocktail with Seasonal Flair

The Perfect Fall Old Fashioned: A Historic Cocktail with Seasonal Flair

A Cocktail Steeped in History

The "Old Fashioned" cocktail was said to have been first made at the Pendennis Club, a gentlemen's club founded in Louisville, Kentucky. A bartender created it in honor of James E. Pepper, a prominent bourbon distiller. So thrilled was Pepper to have a cocktail made for him, he brought the recipe with him on a trip to the big apple and had it recreated at the Waldorf-Astoria Hotel bar. The rest, as they say, is HISTORY.

When Fall Inspiration Strikes

As a long fall day wound down, I decided to toast its passing with an Old Fashioned. Baked apple slices fresh out of my oven begged to be a part of the festivities. Their addition meant little to no sugar was really needed to make this libation sweet. For the sake of history and the flavors of fall filling my kitchen, I decided a dash of orange vanilla sugar would do the trick. Beth calls it "A drunken apple crisp."

Fall Harvest Old Fashioned

Serves 2 | Prep Time: 5 minutes

Ingredients:

  • 8 dashes Apple Angostura Bitters
  • 1/2 tsp orange vanilla sugar
  • 2 Orange wheels
  • 8 slices baked apple slices (reserve 2 for garnish)
  • 4 oz Bourbon (we love Maker's Mark)

Instructions:

  1. Muddle with care: In your cocktail shaker, muddle the bitters, orange vanilla sugar, orange wheels, and 6 apple slices until well combined. The goal is to release the flavors without turning everything to mush.

  2. Add the star: Pour in the bourbon - this is where the magic happens.

  3. The perfect stir: Add ice to your shaker and stir gently 15 times. This technique is crucial - it creates the ideal dilution and temperature while preserving the integrity of your muddled ingredients.

  4. Strain and serve: Divide between two Old Fashioned glasses filled with fresh ice, straining out any large pieces of orange rind.

  5. The finishing touch: Garnish each glass with a reserved baked apple slice.

Why This Version Works

The beauty of this fall twist lies in the orange vanilla sugar. Unlike regular sugar, it adds:

  • Bright citrus notes that complement both the apple and bourbon
  • Vanilla undertones that create depth and warmth
  • Aromatic complexity that makes each sip an experience

The baked apple slices bring natural sweetness and that cozy fall feeling, while the traditional 15-stir technique ensures everything melds together perfectly without over-diluting this classic cocktail.

The Art of the 15-Stir Method

Why exactly 15 stirs? This isn't arbitrary - it's the sweet spot where:

  • The ice provides just enough dilution
  • The temperature drops to the perfect serving point
  • The flavors marry without the muddled fruit breaking down further
  • You maintain the cocktail's strength and character

This Fall Harvest Old Fashioned honors the cocktail's storied past while embracing the season's best flavors. It's proof that sometimes the best innovations come from simply listening to what your kitchen - and the season - are telling you.

Cheers to fall, history, and the perfect Old Fashioned!


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