Classic Pineapple Upside Down Cake

This Classic Pineapple Upside Down Cake recipe is a family favorite for every occasion. Sweet, buttery cake with a hint of pineapple is topped with caramelized pineapple slices and juicy maraschino cherries for a forkful of nostalgia that can’t be beat.


Disclaimer: This post is created in partnership with Harry & David.  All opinions and statements are my own, as always.

We’re finally coming into the home stretch with our pool project.  I ordered chairs the other day and, of course, they’re on backorder but I don’t even care at this point. I’m just ready for that big mountain of dirt I’ve been staring at for months to be gone, fresh new, green grass in the yard and actual water in the pool so I can sit outside with a drink in hand and soak up the sun. Landon’s the only person in the house that’s going to be sad that mountain of mud is finally gone. And we will celebrate with summer foods like fresh fruit salads, fruity cocktails and Classic Pineapple Upside Down Cake….because for some reason, this is the time of year that I can’t seem to get enough pineapple.

Pineapple Upside Down Cake Recipe |

I’m a fan of the Harry & David Fruit of the Month club and frequently send it to friends as a gift.  The gift that keeps on giving.  A new favorite fruit handpicked and delivered each month is the perfect gift for everyone. And This month….they give you the best, juicy fresh pineapple you’ll ever sink your teeth into. I love to cut it up into wedges to garnish cocktails or spears for snacking and salads but my favorite way to use up pineapple is in a Classic Pineapple Upside Down Cake. Sweet and tender, this cake just reminds me of my childhood so much and it’s a ton of fun to make.  I mean, how can it not be fun to build something so beautiful and then turning it out onto a platter to reveal the prettiest dessert you ever did see.

Pineapple Upside Down Cake Recipe |

It all begins with a bit of melted butter that’s drizzled into a cake pan then sprinkled with a healthy dose of brown sugar.  Layer your pineapple slices in the bottom of the cake pan and up the sides, if you like, then arrange your cherries among the slices.

Pineapple Upside Down Cake Recipe |

Pour the vanilla scented cake batter over your fruit. Then, bake until golden and turn out onto a cake plate to reveal your new masterpiece. Always a satisfying display and so much fun to make.  Perfect for every summer party this year.

Pineapple Upside Down Cake Recipe |

Classic Pineapple Upside Down Cake

Prep Time Cook Time Total Time


    For the topping

    • 5 tablespoons melted butter
    • 1/2 cup light brown sugar
    • 6-8 slices pineapple (fresh or canned)
    • 15-20 maraschino cherries, stems removed

    For the cake

    • 1 1/3 cups all-purpose flour
    • 2 teaspoons baking powder
    • 1/2 teaspoon salt
    • 3/4 cup light brown sugar
    • 1/4 cup butter
    • 3/4 cup milk
    • 1 teaspoon vanilla
    • 1 egg
    • 3 tablespoons pineapple juice


    1. For the full recipe visit the Harry & David blog
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    3 comments on “Classic Pineapple Upside Down Cake”

    1. Nothing beats a Pineapple upside down cake. i have always wondered why no one puts cocoanut at the bottom because then you could have a pina colada cake

    2. I had never made an upside cake and always wanted to, so I followed this
      recipe and it turned out great, even though I used fresh pineapple and cherries.

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