In the bottom of your rocks glass (or a cocktail shaker), use a cocktail muddler to muddle the blackberries, mint, sugar, and lime juice together to dissolve the sugar, release the oils from the mint, and break up the blackberries.
Add the bourbon, crushed ice, and club soda to fill the glass. Gently stir with a spoon and serve cold.
To Make a Pitcher of Blackberry Bourbon Smash
To make a nice pitcher of your summer bourbon smash, you'll need...
2 cups fresh (or frozen) blackberries, separated. You want to smash about 1 to 1.5 cups of the blackberries and have some whole for garnish.
¼ cup fresh mint leaves
About ⅓ cup of lime or lemon juice
¼ granulated sugar OR simple syrup. In this case, I'd go with the simple syrup so the sweetness can be fully incorporated throughout the drink.
2 cups of bourbon
2+ cups of club soda or ginger ale
Crushed Ice
This will fill a 2-quart pitcher, so double it if you have a gallon pitcher. Muddle the blackberries, mint, and lime juice (and granulated sugar, if using instead of the simple syrup) at the bottom of your pitcher, then use a wooden spoon or long cocktail spoon to mix the simple syrup (if using), bourbon, club soda, and ice in the pitcher until nice and cold. Serve in pretty serving glasses!