In a chilled mixing bowl, combine the whipping cream and vanilla. Beat with an electric mixer on medium speed until soft peaks form.
In a second mixing bowl, beat together the cream cheese, powdered sugar, and 1/2 teaspoon of the cinnamon with an electric mixer until smooth. Gently fold whipped cream into cream cheese mixture until evenly combined. Transfer mixture to a serving bowl.
In a small bowl, stir together the 2 tablespoons sugar and the remaining 1/2 teaspoon cinnamon. Sprinkle on top of dip. Serve with strawberries, gingersnap cookies, and/or waffle cookies.