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Pineapple Upside Down Cake Jars

Pineapple Upside Down Cake Jars – A Tropical Dessert You Can Hold in Your Hand


  • Author: Sam

Description

Pineapple Upside Down Cake Jars are a fun and portable twist on the classic! Layers of brown sugar-glazed pineapple, moist vanilla cake, fluffy whipped cream, and those signature cherries—all stacked into individual mason jars for a dessert that brings sunshine to any table. Great for parties, picnics, or make-ahead treats. These jars are as beautiful as they are delicious!


Ingredients

Scale

For the Cake:

  • 1 box vanilla or yellow cake mix (plus eggs, oil, and water as required)
    or

  • 1½ cups homemade vanilla cake batter

For the Fruit Layer:

  • 1 can (20 oz) pineapple chunks, drained

  • 1 jar maraschino cherries, drained and halved

  • ¼ cup packed brown sugar

For the Whipped Cream:

  • 1 cup heavy whipping cream

  • 2 tablespoons powdered sugar

  • 1 teaspoon vanilla extract

Optional Garnish:

  • Extra maraschino cherries

  • Toasted coconut flakes

  • Crumbled cake or graham cracker crumbs


Instructions

  1. Bake the Cake:
    Prepare cake mix according to box directions or use your favorite homemade vanilla cake recipe. Bake in a 9×13-inch pan. Once fully cooled, cut the cake into small cubes.

  2. Make the Whipped Cream:
    In a chilled mixing bowl, beat heavy cream with powdered sugar and vanilla until stiff peaks form. Refrigerate until ready to use.

  3. Assemble the Jars:
    In each 8 oz mason jar, start with a spoonful of brown sugar and a few pineapple chunks. Add a layer of cubed cake, then some cherry halves. Repeat with another layer of cake and pineapple. Finish with a generous dollop of whipped cream.

  4. Garnish and Chill:
    Top with a cherry and optional coconut or crumbs. Chill for at least 1 hour. Best enjoyed within 2–3 days.

Notes

  • For a fun twist, add a splash of dark rum or rum extract to your whipped cream or cake batter.

  • Crushed pineapple works well in place of chunks for a softer texture.

  • Cake can be made a day ahead and stored at room temperature in an airtight container.

  • Use Cool Whip instead of whipped cream if you need extra stability for transporting or prepping ahead.

  • These jars are best served cold and will stay fresh in the fridge for up to 3 days.