Step 1: Muddle the Fruits
In a sturdy Old Fashioned glass, add the pitted cherries and fresh blackberries. Use a muddler to gently press the fruit, releasing the natural juices and flavors. The goal is to break down the fruit slightly without completely crushing it, ensuring that the flavors infuse beautifully into the cocktail without creating too much pulp.

Step 2: Add the Sweetener and Bitters
Drop a sugar cube or pour ½ teaspoon of simple syrup into the glass. Add 2 dashes of Angostura bitters. The bitters add depth and complexity to the drink, balancing the sweetness of the fruit and bourbon. If using a sugar cube, muddle it lightly with the fruit until it dissolves into the mixture.

Step 3: Pour in the Bourbon
Slowly pour 2 ounces of bourbon over the muddled fruit mixture. The rich caramel, vanilla, and oak notes of the bourbon will mix with the fresh fruit, creating a delightful contrast of flavors.

Step 4: Stir and Add Ice
Add a large ice cube to the glass. A single large ice cube melts slower than smaller cubes, preventing the drink from becoming overly diluted. Stir gently for about 30 seconds, allowing the flavors to meld and the cocktail to chill.

Step 5: Garnish and Serve
Express the oils from an orange peel by holding it over the drink and gently twisting it to release its aromatic essence. Drop the peel into the glass for extra flavor. Garnish with a fresh cherry and a blackberry on a cocktail pick. Serve immediately and enjoy.