Then make the whipped cream. Whip 1/2 cup of the heavy cream, powdered sugar, 1/2 tsp. of vanilla, and 1/2 tsp. of cinnamon until soft peaks form. Set aside.
In a blender add the coffee, whiskey, maple syrup, remaining heavy cream, remaining vanilla, and remaining cinnamon. Blend for about 30 seconds.
Pour evenly between 2 mugs and top with a generous dollop of the whipped cream.