The pineapple upside-down cake is an American classic. Here, tart apples take the place of honor, sweetened with a mix of white and brown sugar, flavored with cinnamon. It’s a beautiful autumnal dessert, with soft, tender vanilla cake and a subtly flavored bourbon whipped cream spooned on top.

Make-ahead note: Bake the cake 1 day ahead and, when thoroughly cool, wrap it well in plastic film. Rewarm, covered with foil, in a 300°F oven for about 15 minutes.

For more apple cake inspiration, check out our Apple Dapple CakeSpiced Caramel Apple Upside-Down Cake, and Apple Quick Bread with Pecan Streusel.

  • Yields: 8 servings
  • Difficulty: Medium
  • Total: 1 hr 10 mins, plus 20 mins cooling time 
  • Active: 30 mins

Ingredients (15)

  • 3/4 cup granulated sugar
  • 1/4 cup firmly packed light brown sugar
  • 1/2 teaspoon ground cinnamon
  • 8 tablespoons unsalted butter (1 stick), at room temperature
  • 2 cups peeled, cored, and thinly sliced Granny Smith apples (about 2 medium)
  • 1 tablespoon freshly squeezed lemon juice
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/3 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon fine sea salt
  • 1/2 cup whole milk
  • 1 cup heavy whipping cream
  • 3 tablespoons powdered sugar
  • 2 tablespoons bourbon


  1. Arrange a rack in the center and preheat the oven to 350°F. Grease an 8-inch round cake pan.
  2. In a medium bowl, whisk together 1/4 cup of the granulated sugar, the brown sugar, and cinnamon.
  3. Melt 2 tablespoons of the butter in a large frying pan. Add the apples and lemon juice and toss to coat evenly. Add half of the sugar mixture and cook until the sugar melts and the apples begin to soften, about 4 minutes. Transfer the apples to the prepared cake pan. Spread out the slices in a decorative way and sprinkle with the remaining sugar mixture; set aside.
  4. Cream the remaining 6 tablespoons of butter and the remaining 1/2 cup granulated sugar in the bowl of an electric stand mixer until light and fluffy. Add the egg and vanilla extract; beat until well combined, scraping the sides of the bowl as needed.
  5. Combine the flour, baking powder, and salt in a bowl. With the mixer on low speed, add the flour mixture to the butter mixture in three batches, starting and ending with the flour and alternating with the milk. Mix until well combined.
  6. Spoon the batter over the apples in the cake pan, spreading to smooth. Bake the cake until a toothpick inserted in the center comes out clean, 35 to 40 minutes. Let cool on a wire rack for 20 minutes. Run a knife around the edge of the cake and invert onto a rimmed platter.
  7. As the cake cools slightly, whisk together the heavy cream, powdered sugar, and bourbon until soft peaks form. Spoon over warm pieces of cake.