clock clock icon cutlery cutlery icon flag flag icon folder folder icon instagram instagram icon pinterest pinterest icon facebook facebook icon print print icon squares squares icon
Pineapple Upside Down Trifle close up

Pineapple Upside Down Trifles

  • Author: Lindsay
  • Prep Time: 10 minutes
  • Cook Time: 8 minutes
  • Total Time: 18 minutes
  • Yield: 8 Trifles
  • Category: Dessert
  • Method: Stove
  • Cuisine: American


These Pineapple Upside Down Trifles are delicious desserts layered with caramelized pineapple, no bake cheesecake and cinnamon granola! They’re wonderfully easy to make and perfect for celebrations!



  • 24 oz canned pineapple tidbits
  • 1 tbsp butter
  • 1/2 cup brown sugar
  • 810 maraschino cherries, chopped


  • 8 oz cream cheese, room temperature
  • 1/4 cup brown sugar
  • 4 tbsp pineapple juice (reserved from pineapple)
  • 4 oz Cool Whip


  • 2 cups cinnamon granola (I use Bear Naked Original Cinnamon Protein Granola)
  • 2 tbsp pineapple juice (reserved from pineapple)
  • 4 oz Cool Whip
  • 8 maraschino cherries, for garnish
  • 2 pineapple slices, quartered, for garnish


1. Drain the pineapple juice from the cans and reserve about a 1/2 cup of the juice for later.
2. To caramelize the pineapples, add the butter to a medium saucepan on medium hight heat and melt.
3. Stir in brown sugar, pineapple tidbits and cherries.
4. Cook on medium-high, bringing to a simmer, for about 5-10 minutes or until pineapple softens and takes on the caramelized color.
5. Remove from heat and set aside to cool for about 15-20 minutes.
6. To make the cheesecake, add cream cheese, brown sugar and 4 tbsp pineapple juice to a mixer bowl and beat until smooth.
7. Stir in 4 oz of Cool Whip. Set aside.
8. To layer the trifles, first drain the juice from the cooked pineapple and add to a separate bowl. Add 2-3 tbsp of pineapple juice reserved from cans and stir together.
9. Add a layer of cheesecake to the bottom of each glass.
10. Top cheesecake with granola, then sprinkle a little bit of the pineapple juice from step 8 over the granola to give it a little more flavor and help soften it.
11. Top granola with a layer of pineapple.
12. Repeat steps 8-11.
13. Top trifles with some Cool Whip, a cherry and a piece of pineapple, if desired. Refrigerate until ready to serve. Trifles best for 2-3 days.


  • Serving Size: 1 trifle
  • Calories: 379
  • Sugar: 40.7 g
  • Sodium: 274 mg
  • Fat: 14.3 g
  • Carbohydrates: 58.9 g
  • Protein: 6.5 g
  • Cholesterol: 19.7 mg

Keywords: trifles recipe, easy trifles recipe, pineapple dessert, pineapple dream dessert, pineapple recipe, pineapple upside down cake recipe, recipe for trifles