Preheat and prep: Preheat oven to 350°F and line a small baking dish with parchment paper.
Prep the peach: Drizzle 1 ripe but firm peach, halved and pitted with 1 tablespoons olive oil, plus extra for drizzling, a pinch of 0.1 teaspoons salt, and a pinch of 1 teaspoons cinnamon, divided (for brushing and filling). Brush both sides evenly.
First bake: Place peach halves flesh side down in the baking dish and bake.
Make the butter mixture: Mix 0.5 tablespoons butter, 1 tablespoons sugar, remaining 1 teaspoons cinnamon, divided (for brushing and filling), and 0.5 teaspoons vanilla extract together in a small bowl until it forms a smooth paste.
Fill and bake again: Flip the peach halves cavity-side up and spoon the butter mixture evenly into each. Return to the oven and bake.
Cool and top: Let cool a few minutes, then sprinkle with 1 teaspoons raw sugar, for topping, add a drizzle of olive oil, and top with 1 scoop your favorite ice cream.