Pour 1 ounce of the eggnog onto a small plate. On another small plate, mix sugar and cinnamon on another small plate. Dip martini glass in eggnog, and then into the cinnamon sugar mixture. Set aside for cocktail.
Add 2 ounces bourbon, 1 ounce half & half and 2 ounces gingerbread eggnog to a cocktail shaker. Add a generous amount of ice. Shake until ice cold. Strain into the cocktail glass.