Make the ginger simple syrup: Bring water and sugar to a boil. Stir until sugar is dissolved. Remove from heat
Stir in the ginger. Allow to steep for at least 30 minutes. Strain into an airtight container and store in the refrigerator.
Make the cocktail: Place pumpkin butter, orange juice and ginger syrup in a cocktail shaker or glass jar with a lid. Shake vigorously so distribute the pumpkin butter.
Combine the sugar and pumpkin pie spice in a shallow dish. Moisten the rim of a rocks glass with water or orange juice. Dip into the pumpkin pie spice mixture.
Pour pumpkin mixture into the glass. Add the bourbon and stir gently to combine. Fill the glass with ice. Garnish with orange peel and cinnamon stick.