Begin by pouring 1 cup of heavy cream into a mixing bowl. Using an electric mixer, whip the cream on medium speed for about 2-3 minutes until soft peaks form. Transfer to the refrigerator to keep chilled.

Brush a thin layer of maple syrup around the rims of your glasses. Dip the rims into black sanding sugar and place the glasses in the freezer for about 5 minutes.

In a blender, combine 2 cups of vanilla ice cream, 1 cup of milk, ⅓ cup of black cocoa powder, 2 tablespoons of maple syrup, and 1 teaspoon of vanilla extract. Blend on high for 30-45 seconds until smooth and creamy.

Taste and adjust the flavor by adding more black cocoa powder if desired and blend again before serving.

Remove glasses from the freezer, fill with the milkshake mixture, top with whipped cream, and add festive sprinkles before serving.