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Vintage Pineapple Upside-Down Cake

  • Author: Classic Home Baking

Description

A nostalgic dessert featuring caramelized pineapple rings and maraschino cherries atop a moist vanilla cake. This retro favorite is perfect for potlucks or family gatherings.


Ingredients

Scale

For the Crust:

  • For the topping:
  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 oz) can pineapple rings (juice drained and reserved)
  • 1012 maraschino cherries (halved)
  • For the cake:
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter (softened)
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup reserved pineapple juice

Instructions

1. Prepare the Crust:

  1. 1. Preheat oven to 350°F (175°C).
  2. 2. Melt 1/2 cup butter in 10-inch cast iron skillet over medium heat. Stir in brown sugar until dissolved, then remove from heat.
  3. 3. Arrange pineapple rings in single layer over sugar mixture. Place cherry halves in center of rings and between them.
  4. 4. Whisk flour, baking powder, and salt in bowl. In separate bowl, beat 1/2 cup butter with granulated sugar until fluffy.
  5. 5. Beat in eggs one at a time, then vanilla. Alternately add flour mixture and pineapple juice, beginning and ending with flour.
  6. 6. Carefully spread batter over pineapple layer in skillet.
  7. 7. Bake 40-45 minutes until toothpick comes clean. Cool 5 minutes in skillet, then invert onto serving plate.

Notes

For best results, use fresh pineapple rings if available. The cake may stick if inverted too soon – wait exactly 5 minutes. Store covered at room temperature for up to 3 days.