This cocktail is tart from blackberry syrup and lemon juice and fruity without any cloying sweetness. It’s balanced by the caramel flavors in the bourbon and gets creaminess from the sherry. Drink it all season, or at least as long as you can get some decent berries. Rolf and Daughters’ bar director Brice Hoffmann mixed up this new, seasonal cocktail (developed by bartender Reuben Bidez) for one of our editors when she visited Nashville. —Food52
Make the blackberry syrup. In a small saucepan over medium heat, combine water and sugar and mix until sugar has dissolved. Add blackberries and cook for 20 to 30 minutes, until mostly collapsed. Remove blackberry mixture from heat, press through a fine-mesh strainer into a bowl, and let the syrup rest until fully cooled.
Fill a shaker halfway with ice and then pour in the bourbon, blackberry syrup, lemon juice, simple syrup, and oloroso sherry.
Shake vigorously and pour, over ice, into a glass with height.
Express a lemon or orange peel (twist the peel so its oils are extracted) over the drink and add it into the glass. Serve immediately.