Chocolate Cherry Pie Trifles

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I love coming up with unique desserts for the holidays to serve at the holiday table and to give as gifts during the holidays. One of our staple desserts during the holidays is pie.  I love pie and we usually at least have a pumpkin pie and a cherry pie.  My father-in-law is a really big fan of cherry pie, so I always make sure to make it for him.  One thing that we always have with our pies is Cool Whip.  My family is a big fan of whipped cream and we always make sure to have some with our pies.
The holidays are always so busy that I usually just make Mrs. Smith’s pie.  They taste just like homemade and nobody ever notices the difference.  The time I save by using Mrs. Smith’s allows me to get other things done and spend more time with my family.  Even though everyone in my family loves pie, there is always some leftover pie because we like to have a few different kinds.  I always like to take the leftover pie and make a trifle.  That way it is kind of reinventing the pie into a new dessert.
This year instead of making a few different types of pies for the holidays, I decided that I wanted to make trifle out of one of the pies beforehand so that we have a few different types of desserts.  I wasn’t sure what type of pie I wanted to use in the trifle so I headed to Walmart and over to the frozen pie and topping section to decide what I wanted to make so that I could try it out before the holidays. I picked up a Mrs. Smith’s Cherry Pie, my father-in-law’s favorite pie to use to make the trifle.
 I decided to combine the cherry pie with chocolate pudding, since I always think chocolate and cherry go well together.  I then decided to add in Cool Whip to the trifle as well.  I thought that this would be a delicious and easy dessert for the holidays that our family would love and would be different take on our traditional pie during the holiday dinners.
These Chocolate Cherry Pie Trifles taste so fantastic and I cannot wait to make them for our holiday dinner.  The trifles have layers of Mrs. Smith’s cherry pie, including the crust, chocolate pudding, and Cool Whip.  The cherry pie, chocolate pudding, and Cool Whip all taste great together and go well together to make a fantastic dessert.
I decided to serve the trifle in cute mason jars.  These could be served in any cup or container though.  The mason jars I used were a little bigger so they serve about two people as there are two pieces of pie in each mason jar.  You could use smaller mason jars or even use a bigger trifle dish.  These would also be great to use to create a new dessert with your pie leftovers.  These would also make a great romantic dessert for two or would be great to give as gifts around the holidays.  I can’t wait to make these delicious trifles again for our holiday dinners this year.


Chocolate Cherry Pie Trifles


  • 4 slices Mrs. Smith's Cherry Pie
  • 1 box instant chocolate pudding, made according to the directions on the box
  • 1 package (8 ounces) Cool Whip
  • Chocolate Curls (optional garnish)


  1. Make the Mrs. Smith's Pie according to package directions and allow to completely cool.  
  2. Make the chocolate pudding according to the package directions and refrigerate until ready to make the trifle.  
  3. Spoon a slice of cherry pie into the bottom of 2 mason jars or parfait glasses. 
  4. Spoon a layer of chocolate pudding over the cherry pie in each jar or glass.
  5. Add a layer of Cool Whip on top of the chocolate pudding in each jar or glass. 
  6. Repeat each layer.  Garnish with chocolate curls and a cherry on the top, if desired.  The recipe is for 2 large parfaits but you can also make 4 smaller parfaits or double the recipe and use a whole pie to make 4 larger or 8 small trifles.
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  1. This is just amazing!!

  2. Oh, this is such a clever and easy dessert idea! I am pretty much a sucker for any dessert served in cute little glass jars. :) Love this!

  3. I saw this earlier today and was like WHOA. This is such an epic trifle recipe, Alyssa!

  4. OMGosh this is PERFECT. What a fabulous idea Alyssa! Pinned!

  5. I absolutely love how you combined cherry pie with chocolate pudding! These flavors go so well together!

  6. That is so gorgeous!

  7. Beautiful presentation and stress-free assembly. Love it!

  8. This is such a pretty and elegant dessert! Love how easy it is to whip up!

  9. What a fun way to change up how to serve a pie! Love this idea! #Client

  10. This pretty much rocks my world!! Great idea!

  11. That is a gorgeous trifle Alyssa, and so easy to put together!!

  12. A great combination of flavours – and love the presentation too. Beautiful looking food on your blog – saying bonjour via showcase your talent – thanks for hosting too :)

  13. I’m loving everything about this, girl! Especially how quickly it’s made! :)