In a saucepan over low to medium heat, melt 2 tablespoons of unsalted butter. Add 2 cups of diced apples, 1/2 cup of brown sugar, and 1 teaspoon of cinnamon. Stir frequently for about 5–7 minutes, or until the apples soften and the sugar dissolves.

Increase the heat to medium and stir in 1/2 cup of heavy cream and 1 teaspoon of vanilla extract. Continue cooking for an additional 3–5 minutes, stirring constantly, until the mixture thickens slightly.

Once the caramel apple mixture has cooled, add it to a blender along with 3 cups of vanilla ice cream and 1/2 cup of cold milk. Blend on high for about 30-45 seconds or until smooth and creamy.

Prepare your serving glasses by drizzling some caramel sauce inside each glass before pouring in the milkshake. For added fun, sprinkle some graham cracker crumbs at the bottom.

Pour the blended Caramel Apple Pie Milkshake into the prepared glasses and top each shake with whipped cream, graham cracker crumbs, and drizzle extra caramel sauce.