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When ready to cook, start the Traeger grill on Smoke with the lid open until the fire is established (4 to 5 minutes). Set the temperature to 180 degrees F and preheat, lid closed, for 10 minutes.
While Traeger preheats, slice whole orange into wheels.
Place cherries on a small sheet pan. Place orange slices directly on the grill grate.
Smoke cherries for 1 hour and oranges for 25 minutes, depending on taste, before removing from the grill. Let oranges and cherries cool.
Pour Bourbon into glass, followed by simple syrup and bitters. Add ice and stir for 45 seconds or until drink is well-diluted.
Strain contents into new glass over fresh ice. Skewer orange wheel and add cherry for garnish. Enjoy!