Impress your guests when you serve these Pineapple Upside Down Cake Jars.  They are the perfect size for a single serving and your guests will be surprised to find a second maraschino cherry hiding in the bottom of the jar.

These Pineapple Upside Down Cake Jars will be the easiest dessert you ever made and they are absolutely adorable.

Your guests will love having their own little jar of cake to dig into.  They will be like kids when they get to the bottom of the jar and find a second maraschino cherry hiding there.

There are only a few simple steps to making these easy cake jars.


  1. Cut fresh pineapple into 1/2 inch chunks.
  2. Melt some butter in a skillet.  Add the pineapple and some brown sugar and cook until the pineapple is golden brown and slightly soft.


  1. Divide the pineapple mixture and 9 maraschino cherries between nine 8-ounce mason jars.
  2. Mix up a quick cake batter and layer it on top of the pineapple layer.
  3. Bake until the cakes are a light golden brown on top and a toothpick comes out clean.


  1. Place some whipping cream in a large mixing bowl and beat until slightly thickened.  Add some cream cheese, powdered sugar, and vanilla and beat until stiff peaks form.  Note:  The cream cheese acts as a stabilizer for the whipped cream.
  2. Divide the whipped cream topping equally between the 9 jars.  Place a stemmed cherry on top of each one.


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Pineapple Upside Down Cake Jars

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 5 from 1 review
  • Author: Cindy Gibbs
  • Prep Time: 30 Minutes
  • Cook Time: 35 Minutes
  • Total Time: 1 hour 5 minutes
  • Yield: 9 Servings 1x
  • Category: Cake
  • Method: Bake
  • Cuisine: American


These delectable little Pineapple Upside Down Cake Jars are perfect for taking on a picnic, or making just because they’re so darn cute!


Units Scale


  • 2 tablespoons unsalted butter
  • 2 cups chopped fresh pineapple cut into 1/2 inch chunks
  • 1/2 cup light brown sugar
  • 9 red maraschino cherries, without stems


  • 1 1/2 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1 stick unsalted butter
  • 2/3 cup granulated sugar
  • 1 large egg
  • 1/2 teaspoon pure vanilla extract
  • 2/3 cup milk


  • 1 cup heavy whipping cream
  • 3 tablespoons powdered sugar
  • 2 ounces cream cheese, softened
  • 1/4 teaspoon pure vanilla extract
  • 9 red maraschino cherries with stems (or without stems)



Preheat oven to 350 degrees.

  1. Melt the butter in a medium skillet over medium heat.  Add the chopped pineapple and brown sugar and cook, stirring and turning the pineapple every so often until it is golden brown and slightly soft, about 5 to 6 minutes.
  2. Divide the pineapple mixture and maraschino cherries equally between nine 8 ounce mason jars, using a spoon to lightly press and level the mixture in the bottom of the jars.  Set aside.


  1. In a medium bowl, whisk together the flour, baking powder and salt and set aside.
  2. In a large bowl, using an electric mixer, mix the butter and sugar together on medium-high speed until they are light and fluffy, about 2 to 3 minutes.  Add the egg and vanilla and mix on medium speed until well inorporated.
  3. On low speed, add one half of the flour and the milk, followed by the remaining flour, and mix just until it is incorporated.  Do not over mix.
  4. Divide the batter equally between the jars, using a spoon to level out the batter.
  5. Transfer the jars to a cookie sheet, spacing them apart, and bake until the cakes are a light golden brown on top and a toothpick inserted into the cake part comes out clean, about 30 to 35 minutes.  Transfer the cakes to a wire rack to cool slightly.  Refrigerate until they are totally cool.


  1. Add the whipping cream to the bowl of a stand mixer, or use a hand mixer.  Beat the whipping cream on medium speed until it begins to slightly thicken.  Turn mixer to high and beat until soft peaks form.  Add the powdered sugar, cream cheese and vanilla and beat until stiff peaks form.
  2. Divide the topping equally between the cooled jars.  Place one maraschino cherry with stem on top of each one.
  3. Serve immediately or refrigerate.  See notes below.


  • The cream cheese acts as a stabalizer in the whipped cream.  You can leave the jars out at room temperature for quite a while and the whipped cream will remain stable.
  • I suggest not putting the topping on the cakes until you’re ready to serve them.  That way you can place the lids on the jars, keeping them fresh, and leave them at room temperature for serving.  You can even slightly warm the cakes if preferred, before adding the topping.