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Author Notes: I love culinary takes on cocktails. Winter spices and warm roasted butternut squash are infused into bourbon; creating a drink with deep earthy sugar and spice flavors. —Sippity Sup (Greg Henry)
- 1 small butternut squash (about 1 pound)
- 1 (750 ml) bottle bourbon
- 4 whole star anise pods
- 1 tablespoon whole fennel seeds
- 1 (3-inch) cinnamon stick, broken into pieces
- 1 teaspoon lightly cracked, whole cloves
- 1 teaspoon lightly cracked, whole black peppercorns
- 1/2 cup granulated sugar
- 1/2 cup water
- 2 1/2 ounces prepared squash-infused bourbon
- 1/2 ounce prepared five-spice syrup
- 1-2 dashes Angostura bitters
- ice cubes (as needed)
- 1 wide strip of orange peel (as garnish)
- Make the squash-infused bourbon: Place the oven rack in the center position and preheat the oven to 450°F. Place the whole butternut squash on a baking sheet and bake until blistered and soft enough that you can easily pierce the skin with a knife, about 1 1⁄2 hours. Remove from the oven and set aside until cool enough to handle but still quite warm.
- Cut the squash in half lengthwise and scoop out the seeds and fibers from the center and discard them. Pull off the skin and discard it. Cut the flesh into 2-inch chunks. Place the pieces in a large, nonreactive container. Add the bourbon while the squash is still warm; this will help the infusion process. Cover and set aside in a dark area for 3 days, swirling the mixture occasionally. Taste the infusion; it should have a pronounced sweet squash flavor. If so, strain the liquid through a sieve, lined with a double layer of damp cheesecloth, discarding the solids. This infusion makes more than you need for just one cocktail, but it can be covered and refrigerated for up to 1 month.
- Make the five-spice syrup: Add star anise, fennel seeds, cinnamon stick pieces, cloves, and peppercorns to a small, dry saucepan set over medium-high heat, shaking the pan often, until noticeably fragrant, about 2-3 minutes. Stir in sugar and water and heat until it just begins to reach a low boil. Adjust the heat to keep the liquid at a simmer for 5 more minutes, turn off heat and steep the syrup for an hour. Strain the syrup through a fine-mesh sieve then place it in a lidded container and store in the refrigerator. Bring to room temperature before using.
- Make the cocktail: Add the prepared squash-infused bourbon, prepared five-spice syrup, and bitters to a cocktail shaker and fill the shaker with ice cubes; shake until well chilled. Double-strain through a fine-mesh sieve into an Old-Fashioned glass filled with three medium or one extra-large cube of ice. Twist, spritz, and garnish with a wide strip of orange peel.
- This recipe was entered in the contest for Your Best Savory (Winter) Squash Recipe