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1
Make the squash-infused bourbon: Place the oven rack in the center position and preheat the oven to 450u00b0F. 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.
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2
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.
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3
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.
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4
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.
