Pineapple Upside Down Trifles

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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!

Want to make the original retro cake? Try my easy pineapple upside down cake recipe.

Ashton Baby Shower announcement

Pineapple Upside Down Trifles Recipe

What’s the occasion? Today I and a handful of other bloggers are celebrating Ashton from Something Swanky’s virtual baby shower! She is due very soon with a baby boy, so join me in congratulating her!

I have long loved Ashton’s blog and she’s just as sweet in person as she is on her blog. Plus, she’s a fellow North Carolina native and sweets lover. 🙂 Her and her husband already have an adorable little girl, so I can only imagine how adorable this baby boy will be.

To celebrate the occasion, I brought these Pineapple Upside Down Trifles to the virtual party. They work great for an occasion like a baby shower given that they are individual desserts, but would also be great for any time. They are really easy to make, which is great if you have a whole party to prepare for.

A lot of the great flavor that comes in a pineapple upside down cake is from the pineapple that caramelizes in the butter and brown sugar while the cake cooks. All that delicious-ness bakes into the cake too, giving it that moist, wonderful flavor. I wanted to make sure I kept that caramelized element in these trifles.

Pineapple Upside Down Trifles in glass cups on a yellow cake stand
Pineapple Upside Down Trifles in glass cups on a tray

How to Make Pineapple Trifles

So to start, the pineapple layer is made by cooking the fruit in butter and brown sugar. It softens the pineapple and gives it that caramel-y flavor that is so wonderful. I added some chopped cherries to it, because I love them in the cake, but they could be left out if you aren’t into cherries.

The cheesecake layer is a no bake cheesecake that has some brown sugar and pineapple juice in it, further reinforcing the wonderful flavors of the classic cake. It’s easy to put together, as it’s all just combined with a mixer and then added to the trifles.

I layered my trifles with a cinnamon granola, but you could also use pound cake or angel food cake if you preferred. I love the crunch and extra flavor from the granola personally. It also softens up a fair bit when the trifles are refrigerated so it ends up adding great texture, without being too much crunch.

Close-up of Pineapple Upside Down Trifles in glass cups
Pineapple Upside Down Trifles in glass cups on burlap

To layer the trifles, alternate adding each of the three layers. You should end up with two of each layer. The glasses I used are little 8 ounce glasses that work great. You could also use the 8 ounce size mason jars. They’re a little smaller than the typical mason jar and I usually can find them pretty easily at Hobby Lobby.

These trifles were a big hit! They are such a fun flavor and with the fruit and granola, it’s basically healthy. I mean, you could almost call it breakfast. Unless you decided to replace the granola with cake. Then it’s dessert. But you can totally have dessert for breakfast. I won’t tell. 🙂

And once again, congratulations Ashton!

Be sure to check out the other recipes served at Ashton’s virtual shower today!

Krispy Kreme Pie by Wine and Glue
How to Make Lemon Mini Cupcakes by Call Me PMC
Brown Sugar Butterscotch Bundt Cake by Layers of Happiness
Double Chocolate Cups by Diary of a Recipe Collector
Strawberries and Cream Skillet Cobbler by Taste and Tell
Paleo Blueberry Coconut Cupcakes by Food Faith Fitness
Blueberry Coconut Protein Pops by Capturing Joy
Strawberry Pretzel Salad Dip by Crazy for Crust
Creamy Lemon Angel Cake Roll by Yummy Healthy Easy
Blueberry Granola Gratin by Buns in My Oven
Strawberry & Cream Profiteroles by Lemons for Lulu
Dirt Cake by In Katrina’s Kitchen
S’mores Frappuccino Cupcakes by Inside BruCrew Life
Butterfinger Cupcakes by Six Sisters’ Stuff
Brookie Bars by It Bakes Me Happy
Carrot Cake Cupcakes by Beyond Frosting
Blueberry Pie Cheeseball by Mom On Timeout
No-Bake Blueberry Cheesecake Mousse by Heather’s French Press
Blueberry Cream Cheese Cookies with a Lemon Glaze by The Recipe Critic
Lemon Berry Pastries by I Wash You Dry
Lemon Berry Fruit Kabobs by Crumbs and Chaos


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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 flavor-packed Pineapple Upside Down Trifles are layered with caramelized pineapple and cherries, no bake brown sugar cheesecake and cinnamon granola! They’re wonderfully easy to make and perfect for celebrations!


Pineapple Cherry Layer

  • 24 oz canned pineapple tidbits
  • 1 tbsp (14g) butter
  • 1/2 cup (112g) brown sugar
  • 810 maraschino cherries, chopped

No Bake Brown Sugar Cheesecake Layer

  • 8 oz (226g) cream cheese, room temperature
  • 1/4 cup (56g) brown sugar
  • 4 tbsp pineapple juice (reserved from pineapple)
  • 4 oz Cool Whip

Additional Ingredients

  • 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


Make the Pineapple Cherry Layer

  1. Drain the pineapple juice from the pineapple tidbits and slices. Reserve about a 1/2 cup of the juice for later. Set pineapple and juice aside.
  2. Begin the caramelization process by adding the butter to a medium saucepan on medium high heat and melt.
  3. Cook on medium-high, bringing to a simmer, for about 5-10 minutes or until pineapple softens and takes on a golden caramelized color.
  4. Remove from heat and set aside to cool for about 15-20 minutes.

Make the Brown Sugar Cheesecake Layer

  1. To make the cheesecake, add cream cheese, brown sugar and 4 tbsp pineapple juice to a mixer bowl and beat until smooth.
  2. Stir in 4 oz of Cool Whip. Set aside.

Assemble the Trifles

  1. Make a quick pineapple sauce by draining the juice from the cooked pineapple and add it to a separate bowl. Add 2-3 tbsp of reserved pineapple juice and stir together. Set aside.
  2. Place eight 8 oz cups or jars in front of you and add a layer of cheesecake to the bottom of each container.
  3. Top cheesecake layer with granola, then sprinkle a little bit of the pineapple sauce over the granola to give it a little more flavor and help soften it.
  4. Top granola with a layer of pineapple and cherries.
  5. Add another set of layers to each container; start with cheesecake and proceed to granola, pineapple sauce and caramelized fruit.
  6. Cut both pineapple rings into quarters. You should have 8 pieces to top the trifles with.
  7. Top trifles with some Cool Whip, a cherry and a quartered pineapple slice, 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

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Pineapple Upside Down Trifles in glass cups on a tray

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Pineapple Coconut Bars
Caramel Apple Trifles
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Triple Berry Trifle

About Lindsay

I'm a wife and a mom to twin boys and a baby girl! And I've got a serious sweets addiction! Bring on the treats!

Scripture I’m Loving

“Come to me, all you who are weary and burdened, and I will give you rest. Take my yoke upon you and learn from me, for I am gentle and humble in heart, and you will find rest for your souls.” Matthew 11:28-29