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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.
Pineapple Upside Down Trifles Recipe
I’ve had the opportunity to go to a lot of baby showers, and I love making individual desserts for them, like these Pineapple Upside Down Trifles. They work great for parties and special occasions, but would also be great for any time. They are also really easy to make, which is great if you’re short on time.
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.
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.
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. 🙂
More Pineapple Dessert Recipes
- Pineapple Coconut Bars
- Fruit Cheesecake Sugar Cookie Cups
- Pineapple Layer Cake
- Pineapple-Upside Down Cheesecake
- Pineapple Upside Down Cake
Pineapple Upside Down Trifles
- Prep Time: 10 minutes
- Cook Time: 8 minutes
- Total Time: 18 minutes
- Yield: 8 Trifles
- Category: Dessert
- Method: Stove
- Cuisine: American
Description
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!
Ingredients
Pineapple Cherry Layer
- 24 oz canned pineapple tidbits
- 1 tbsp (14g) butter
- 1/2 cup (112g) brown sugar
- 8–10 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
Instructions
Make the Pineapple Cherry Layer
- 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.
- Begin the caramelization process by adding the butter to a medium saucepan on medium high heat and melt.
- Cook on medium-high, bringing to a simmer, for about 5-10 minutes or until pineapple softens and takes on a golden caramelized color.
- Remove from heat and set aside to cool for about 15-20 minutes.
Make the Brown Sugar Cheesecake Layer
- To make the cheesecake, add cream cheese, brown sugar and 4 tbsp pineapple juice to a mixer bowl and beat until smooth.
- Stir in 4 oz of Cool Whip. Set aside.
Assemble the Trifles
- 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.
- Place eight 8 oz cups or jars in front of you and add a layer of cheesecake to the bottom of each container.
- 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.
- Top granola with a layer of pineapple and cherries.
- Add another set of layers to each container; start with cheesecake and proceed to granola, pineapple sauce and caramelized fruit.
- Cut both pineapple rings into quarters. You should have 8 pieces to top the trifles with.
- 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.
Nutrition
- 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
Enjoy!
I love pineapple! These trifles look gorgeous Lindsay!
I mean since it has fruit and granola I’d consider it a breakfast food 😉 Looks delicious and SO PRETTY!!
Such a fun way to switch up the pineapple upside down cake! I love trifles, and this one is genius.
This is such a great twist on upside down cake. LOVE the granola in there!
Dang girl! You outdid yourself with this trifle!
I’ve never been completely on board with pineapple upside down cake, but these look fantastic! Is there a granola brand or recipe you can suggest? I’m dying to try the cheesecake layer with the pineapple juice and brown sugar. Yum!
Yes, I like this one, but I’ve also used the ALDI brand, if you have one of those stores nearby. I added the note to the ingredients as well. Thanks! 🙂
This virtual baby shower is the cutest thing ever 🙂 And your pineapple upside down trifles… I’d love to eat one right now, they look amazing!
what a beautiful trifle I am buts for anything served individual style such a fun recipe 😉
These are gorgeous, and your photography is simply stunning (as always)! Thank you so much for the sweet post! You guys are the best 🙂
pineapple in butter and brown sugar, sign me up! this looks delicious
Lindsay, it’s like we’re on the same wave length! You posted your awesome orange creamsicle cake this week and I shared an orange poppyseed cake, now you have pineapple upside down trifles and I have pineapple upside down monkey bread coming! This is definitely something we’d devour!
Ashton is so fantastic! These are seriously such a beautiful way to celebrate with her!!
Very sweet to do this for Ashton. I’m sure she loves it, and it looks great!