Pineapple Upside Down Cake Jars

  • Author: Cindy Gibbs
  • Prep Time: 30 Minutes
  • Cook Time: 35 Minutes
  • Total Time: 1 hour 5 minutes
  • Yield: 9 Servings 1x


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




  • 2 tablespoons unsalted butter
  • 2 cups chopped fresh pineapple cut into 1/2 inch chunks
  • 1/2 cup light brown sugar
  • 9 red marachino 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 vanill extract
  • 9 red marachino 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.
  • Category: Cake
  • Method: Bake
  • Cuisine: American

Keywords: pineapple upside down cake jars, pineapple, upside down cake,