It’s pineapple time! Bold and refreshing Harry & David pineapples are a juicy treat that’s wonderful all on their own. Cut into spears or wedges, they make an excellent snack any time of day, but I like to mix things up by throwing them into my dessert recipes like this classic pineapple upside down cake.

Tender and moist, this cake is topped with perfectly caramelized fresh pineapple slices and sweet maraschino cherries, making it a fun centerpiece for your dessert table. And it couldn’t be easier to make!

It all begins with a bit of melted butter that’s drizzled into a cake pan then sprinkled with brown sugar. Layer your pineapple slices on the bottom of the cake pan (even try placing slices up the sides of the pan, if you like), then arrange your cherries among the slices. Pour the vanilla scented cake batter over your fruit, then bake until golden. Turn it out onto a cake plate to reveal your new masterpiece.

Classic Pineapple Upside Down Cake

5 from 1 vote
Prep Time 40 minutes
Cook Time 45 minutes
Resting time 15 minutes
Total Time 1 hour 40 minutes
Servings 8


  • 1 10 inch deep dish cake pan


For the topping

  • 5 tablespoons melted butter
  • ½ cup light brown sugar
  • 6-8 slices pineapple
  • 15-20 maraschino cherries (stems removed)

For the cake

  • 1 ⅓ cups all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ¾ cup light brown sugar
  • ¼ cup butter
  • ¾ cup milk
  • 1 teaspoon vanilla
  • 1 egg
  • 3 tablespoons pineapple juice


  • Preheat oven to 350˚ Fahrenheit.
  • Pour melted butter into the bottom of a 10 inch deep dish cake pan and sprinkle the brown sugar evenly over top.
  • Arrange the pineapples and cherries on top of the butter mixture and up the sides, if desired. Set aside.
  • In a medium bowl, whisk together the flour, baking powder and salt. Set aside.
  • In a large bowl, beat the brown sugar and butter together until smooth. Turn the mixer to low and, slowly add the milk, vanilla, egg and pineapple juice until combined.
  • Add the dry ingredients to the wet mixture beating until combined and no lumps remain.
  • Pour the batter over the pineapple and spread evenly — some of the fruit may poke through the batter.
  • Bake for 45 minutes or until golden brown and the top springs back when pressed with your finger.
  • Allow the cake to cool in the pan for 5 minutes then turn the cake out onto a cake plate or platter and leave the pan on the cake for 10 minutes longer.
  • Remove the pan and allow to cool to room temperature or serve warm, if desired.
Course: Dessert
Cuisine: American
Keyword: cake, pineapple
Tried this recipe? Snap a pic and share.Mention @harryanddavid or tag #sharemore!

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  1. Avatar photo
    celestine landrum Reply

    I would love to have the recipe for Classic Pineapple Upside Down Cake. I cannot print the recipe only. It looks so good, would love to make it.

  2. Avatar photo
    Megan Davis Reply

    Wow! This is like the best recipe I’ve come across. I will make this for my Moms birthday. Thank you!

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