Place first five ingredients into a small saucepan and simmer over medium heat until the sugar dissolves, stirring occasionally. This should take about 5 minutes.
Bring the mixture to a boil then cover and remove from heat. Allow the mixture to steep for 30 minutes. This will allow all the spices to infuse the simple syrup with flavor. Place a strainer over a glass measuring cup, and strain the spices from the simple syrup. Reserve the simple syrup, cool completely and store in your refrigerator for about 1 hour. Discard the spices. The simple syrup will last up to 1 week in your fridge, so if you plan on making these for a fall party make the simple syrup a couple of days ahead of time.
Place one orange wedge into the bottom of each of the four glasses and muddle together. If you don’t have a muddler, use the end of a flat rolling pin to press down repeatedly on the orange wedges, which will release their juice into the glass. Place the chilled syrup, bourbon and ice into a large shaker and shake until well combined. Divide the mixture into each glass and top with an extra orange wedge, squeezing the wedge before dropping into the glass.
Garnish each glass with a cinnamon stick and serve immediately.