Add all the ingredients into a shaker and shake vigorously.
Double-strain into a double-rocks glass over ice, and garnish with freshly grated nutmeg.
*Green acorn squash cordial: Add 1.5 cups of squash purée, 1 cup granulated sugar and .5 tsp of whole allspice into a saucepan, and bring to a simmer, stirring slowly. Remove from the heat and allow to cool to room temperature. Once cool, strain through fine-mesh cloth into a clean bowl. Stir in 1 cup of vodka in the mixture until combined. Use immediately or refrigerate in an airtight container for up to 1 week.
**Roasted white acorn squash purée: Quarter and deseed a whole squash, then pierce the squash flesh with 10 to 12 cloves, depending on the size of the squash. Roast at 414°F in an oven-safe pan until the flesh is tender. Allow to cool and remove the cloves. Place the cooled squash in a blender, and pulse until smooth, streaming in cold water until the desired purée consistency is reached. Use immediately or refrigerate in an airtight container for up to 1 week.