Add bourbon, apple cider, maple syrup, and bitters.
Stir gently for about 20–30 seconds to chill and mix.
Strain into a rocks glass over a big ice cube.
Express the oils from an orange peel over the drink and drop it in.
Garnish with a cinnamon stick and an orange slice.
Notes
Swap in half apple brandy for a fruitier twist or use maple bourbon for extra sweetness without additional syrup. Reduce bourbon to 1.5 oz and increase cider for a lighter version. Cinnamon stick slowly infuses spice as you sip.