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Preheat oven to 350°F. Grease and flour two 9-inch round baking pans; set aside.
In an extra-large bowl, combine buttermilk, water, oil, 2 cups sugar, eggs, baking soda and salt. Using a large wire whisk, whisk until well combined. Add flour and cocoa powder; whisk vigorously until smooth. Divide batter between prepared pans.
Bake for 30 to 35 minutes until tops spring back when lightly touched in center. Cool in pans on a wire rack for 10 minutes. Remove from pans and cool completely.
In a medium bowl, whisk together cream cheese, pumpkin, the remaining 1/4 cup sugar and cinnamon until thickened. Place one cake layer on plate. Spread filling over top. Top with second cake layer.
In a saucepan, bring whipping cream just to a boil over medium-high heat. Remove from heat. Add chocolate (do not stir). Let stand 5 minutes. Stir until smooth. Cool 15 minutes or until slightly thickened. Pour over cake, allowing glaze to drip down sides. Chill until set, about 30 minutes. Top with grapes and/or other desired toppers.