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Pineapple Upside Down Cake Classic Skillet Recipe

 Pineapple Upside Down Cake 

Pineapple Upside Down Cakes is a rich vanilla cake on the bottom with a dark crisp brown sugar topping sweetened with pineapple rings and maraschino cherries.  The butter and brown sugar topping make a rich caramel glaze. A traditional dessert in the spring for Easter dinner as well as a bright flavored spring and summer dessert. 

For our family, at Easter dinner one of the traditional desserts we have served for years is a traditional pineapple upside-down cake recipe. My mother always made pineapple upside-down cake in the spring and summer as a light Sunday dessert. 

Jim’s mother has a fabulous skillet recipe that I have made once we got married.  I do not have many recipes from my mother so I have loved that Jim’s mom shared her recipes from the ’40s and ’50s.  Both my mom and Jim’s mom were married, raising their children, and being creative cooks in these years

Easter Menu Pineapple Upside Down Cake Recipe, in cast iron skillet

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I want to share our family’s traditional skillet pineapple upside-down cake which we make every Easter.  I also have a new pineapple-shaped baking pan I found in the closeout aisle at a kitchen store.  I loved the cute shapes and I was planning a dinner party and wanted a dessert.  This pan was so unique and I could make individual servings.  Nordic Ware Pineapple Upside Down Mini Cake Pan 

The Cake batter is rich and delicious with a hint of vanilla.  The butter brown sugar glaze seeps down into the cake while cooking and adds to the flavor. The pineapple rings and cherries add just a bit of extra natural sweetness and a bright spring coloring. They all most look like flowers. 

You can add more pineapple bits to the top and more cherries to the top if you want to load it up.  If the cherries are not your favorite, you can substitute pecans for the middle. I always keep a jar of the maraschino carries in my pantry along with 2 cans of pineapple rings so any weekend when we want a fun dessert I can make this recipe so simple and quick. 

Easter Menu Pineapple Upside Down Cake Recipe, cake on pink platter with bunny napkin and cake server

Why a Cast Iron Skillet for your Pineapple Upside Cake?

Our family recipe calls for a large cast-iron skillet.  However, you can use any baking round pan. The cast iron adds a depth of color to the caramelized top and adds more iron to your diet. If you do not have a cast-iron skillet this is the time to buy one.

They are so easy to use, you just need to make sure it is very very dry after rinsing or washing as they will rust if left out wet. Cast iron adds much need iron to a lot of people’s diet and can be kept for generations.  I have my mother’s that is probably over 90 years old.

Your cast iron skillet is indestructible and can be good indoors as well as on your grill on a campfire. If cared for properly are non-stick. It is chemical-free.  When you buy yours make sure to read the directions for washing and storing. They are so easy to use and will make your food taste better.

One of the best features is you can use any type of utensil on it most importantly metal. Never worry about scratching a pan again. 

pineapple upside down cake with wedge cut out

Supplies Needed: 

  1. Cast Iron Skillet
  2. Mixing Bowls
  3. Maraschino Cherries
slice of cake on a green and yellow plate with fork

Serving Pineapple Upside Down Cake

Serve this cake right out of the skillet after you turn it upside down. It is delicious warm with whip cream, instant whip topping, or a scoop of vanilla ice cream. 

After one day I like to store the cake in the fridge.  You can then reheat in the microwave or it is still super delicious cold. We mostly set the cake out on the counter to come to room temperature and top with lots of Redi Whip. 

Tip for New Cooks

Both this traditional skillet pineapple upside-down cake recipe and the mini pancake recipe are basic and simple. Just gather your ingredients before you start and it will be mixed in no time.   

The cakes keep well if you need to make a dessert ahead if you are having friends over or going to a family function.  If you have only baked from a box mix do not be afraid. This is very simple with simple ingredients.

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Pineapple Upside Down Cake Classic Skillet Recipe

This Batter has a rich vanilla flavor that puffs up when baked, with a butter brown sugar caramelized glaze.

  • Total Time: 1 hour 10 minutes
  • Yield: 8 servings 1x


Units Scale

For the bottom of the cast iron skillet:

  • 1 cup Brown Sugar
  • 2 Tablespoons of Butter

To Add to the skillet after the brown sugar and butter:

  • 2 cans of pineapple rings in natural juices
  • 2 jars of maraschino cherries

For the cake batter:

  • 1/3 cup of butter, room temperature (softened)
  • 1 cup White sugar
  • 2 eggs
  • 1 & 3/4 cups flour
  • 2 tsp baking powder
  • 1/4 tsp salt
  • 1/2 cup Milk
  • 1 tsp Vanilla


  1. Place a large 11-inch cast-iron skillet on medium heat.
  2. Add the 1/3 cup butter and 2 tablespoons of butter to the skillet and melt. Turn off the heat.
  3. Next, add the pineapple rings on top of the melted butter and brown sugar in the skillet. Cut some in half or in 1/4 to cover as much of the skillet as you can.
  4. Add to the center of each Pineapple ring a Maraschino Cherry.
  5. Next, make the cake batter
  6. In a large bowl, with a stand or hand mixer, cream the 1/3 cup of softened butter and the one cup sugar, beat until well mixed, add the 2 eggs and beat until fluffy.
  7. In a separate medium bowl sift together with a sifter or shake together with a strainer the flour, baking powder, and salt.
  8. Measure the milk and add the vanilla to the milk
  9. Combine the flour mixture and the milk mixture to the butter-sugar mixture 1/3 at a time until it comes together, do not over mix.
  10. Pour the cake batter into the skillet over the pineapple rings.
  11. Bake at 325° for 40 minutes. Let stand for 5 minutes and then invert onto a serving platter.


  1. Do not leave too long in the skillet after baking or the sugar will stick to the bottom and you will not be able to get that fabulous look on top.
  • Author: Crafting a Family
  • Prep Time: 30 minutes
  • Cook Time: 40 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American


  • Serving Size: 8

Keywords: Pineapple Upside Down Cake

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  1. This is one of those awesome traditional recipes from our mothers generation. It’s the perfect recipe for new bakers. I have not made this in a very long time. It’s time to make one again. Thanks

  2. I adore Pineapple upside down cake it is so good – never tried it in a skillet I must try this Susan.

    1. Thank you so much! The cake is a little heavier than a box mix but so much better.

  3. Thanks for Bringing Your Post on the Pineapple upside down Easter Cake… to the Blogger’s Pit Stop 🙂 Looks Super yummy!
    Pit stop Crew

  4. Roseann Hampton says:

    I love pineapple upside cake! Thanks for sharing your recipe!

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