Combine all ingredients and pour over ice. Garnish with orange peel and a blueberry.
To make Squash-Infused Bourbon:
Cut 2 cups acorn squash into chunks.
Toss squash with 1/4 cup maple syrup and 1 teaspoon cinnamon.
Spread on a baking sheet and bake in the oven at 350 degrees for 15 minutes or until soft. Allow to cool.
In a large jar, combine the squash with 1 750mL bottle of bourbon; save the bottle for later.
Cover jar tightly and allow it to infuse for two to three weeks.
Strain the bourbon, funnel back into the empty bottle and cap tightly.