Preheat oven to 375 degrees F. Toss cherries with olive oil and salt then place on a baking sheet and roast for 25 minutes, tossing once or twice in between. Let cool. (This can be done ahead of time!)

To make shakes, combine ice cream, milk, bourbon and cherries in a blender and puree until smooth. Drizzle hot fudge over the inside of each glass, then pour in milkshake. Top with whipped cream, cacao nibs and a cherry.