Fun Craft Cocktails

November 15, 2025

Pumpkin Whiskey Smash

The Pumpkin Whiskey Smash is a modern, fall variation of the classic Whiskey Smash which dates back to the late 1800’s. It was first published in 1887 in Jerry Thomas’s Bartender Guide and was originally a mixture of sugar, water, mint, spirit such as whiskey, gin or brandy and a “seasonal fruit”. It was then reintroduced in the 1980s-90s at the Rainbow Room in New York City by celebrated bartender Dale DeGroff and again popularized in the 2000s where the seasonal pumpkin version arose especially for the fall/Thanksgiving season. I’ve teamed up with Dented Brick Distillery and am using their Bottled in Bond Rye Whiskey, which is a celebration of the bottled in bond act of 1897 that ensured consumer quality. Cheers!

Equipment

  • Cocktail Shaker
  • Jigger
  • Double Rocks Glass
  • Large Square Ice Cube Mold
  • Paring Knife
  • Cutting Board
  • Small Saucepan
  • Measuring Cup
  • Measuring Spoon
  • 2 Toothpicks

Ingredients – Serves 1

  • 2 oz Rye Whiskey (Dented Brick)
  • 1 oz Pumpkin Syrup
    • 1/2 cup Maple Syrup
    • 1/3 cup Water
    • 1/3 cup Pumpkin Puree
    • 1/2 tsp Pumpkin Pie Spice
    • 1 tsp Vanilla Extract
    • Sea Salt
  • 2 oz Apple Cider
  • 2 dashes Orange Bitters
  • Cinnamon Stick for Garnish
  • Orange Peel for Garnish
  • Star Anise for Garnish

Method

  1. Prepare the Large Ice Cubes. Using a large square ice cube mold, fill with filtered water and place in the freezer. It takes 24 hours to freeze a large ice cube.
  2. Make the Pumpkin Syrup. Combine all syrup ingredients in a small saucepan. Stir. Heat to boil. Boil 1 minute. Remove from heat and let cool. Transfer to a glass container and keep in fridge for up to 2 weeks. This will make enough for about 6 cocktails.
  3. Prepare your Garnish. Wash and dry an orange. Using a paring knife or peeler, cut a long strip of orange peel (try to go around the entire center of the orange). Trim the sides down so the strip is about 1/4 inch wide. Trim the ends. Wrap the peel around a cinnamon stick and secure with toothpicks on each end (use the open crack of the cinnamon stick to insert the toothpick). Trim the ends of the toothpicks with scissors.
  4. Make the Cocktail. Add the whiskey, pumpkin syrup, apple cider and orange bitters to a cocktail shaker with ice. Shake to combine. Place a large square ice cube into a double rocks glass. Strain the cocktail into the glass.
  5. Garnish. Place the orange peel wrapped cinnamon stick in the cocktail and the star anise on top of the ice cube. Cheers!

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